Similarity of High-Resolution Tandem Mass Spectrometry Spectra of Structurally-Related

Appendix A

SupplementaryMaterial for:

Similarity of High-Resolution Tandem Mass Spectrometry Spectra of Structurally-Related Micropollutants and Transformation Products

Jennifer E. Schollée,*,a,b Emma L. Schymanski,a Michael A. Stravs,a,b Rebekka Gulde,a Nikolaos S. Thomaidis,c and Juliane Hollendera,b

aEawag, Swiss Federal Institute of Aquatic Science and Technology, 8600 Dübendorf, Switzerland

bInstitute of Biogeochemistry and Pollutant Dynamics, ETH Zürich, 8092 Zürich, Switzerland

cLaboratory of Analytical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, 157 71 Athens, Greece

*Corresponding Author

Journal of The American Society for Mass Spectrometry, 2017

Table of Contents

Section S1. Comparison of spectra measured on multiple Orbitrap instruments

Section S2. LC-QTOFMS measurement settings

Section S3. Table of Structurally Related and Unrelated Pairs

Section S4. Fragment Analysis

Section S5. Summary of the Weighting Factors

Section S6. Single Collision Energy Analysis

Section S7. Absolute Intensity vs. Relative Intensity Merging

Section S8. Influence of the Monoisotopic Peak on Similarity Scores

Section S9. Analysis of QTOF data

Section S10. Structural Similarity and Spectral Similarity

Section S11. Transformation Type

Section S12. References

Section S1.Comparison of spectra measured on multiple Orbitrap instruments

Figure S1.(a) to (m) show the comparison of spectra collected for the 13 compounds that were measured on two different Orbitrap instruments. Indicated in the top two lines of the legend are the instrument types. In the bottom two lines of the legend are the resolution of the measurement, followed by the normalized collision energies (NCEs) used for measurement. It is clear that in all cases, fragmentation was very similar of the two instruments, with mostly only slight differences in intensity observable.

Section S2. LC-QTOFMS measurement settings

Analyses were carried out using a UHPLC/QTOF-MS system, equipped with a UHPLC apparatus (Dionex UltiMate 3000 RSLC, Thermo Fisher Scientific, Dreieich, Germany), consisting of a solvent rack degasser, auto-sampler, a binary pump with solvent selection valve and a column oven coupled to the QTOF-MS mass analyzer (Maxis Impact, Bruker Daltonics, Bremen, Germany).

The chromatographic separation was performed on an Acclaim RSLC C18 column (2.1 × 100 mm, 2.2 µm) from Thermo Fisher Scientific (Dreieich, Germany) preceded by a guard column of the same packaging material, kept at 30˚C. For positive ionization mode (PI), the aqueous phase consisted of H2O/MeOH 90/10 with 5 mM ammonium formate and 0.01% formic acid and the organic phase was MeOH with 5 mM ammonium formate and 0.01% formic acid. For negative ionization mode (NI), the aqueous phase consisted of H2O/MeOH 90/10 with 5 mM ammonium acetate and the organic phase was MeOH with 5 mM ammonium acetate. The adopted elution gradient for both ionization modes started with 1% of organic phase (flow rate 0.2 mL min-1) for one minute, increasing to 39 % by 3 min (flow rate 0.2 mL min-1), and then to 99.9 % (flow rate 0.4 mLmin-1) in the following 11 min. These almost pure organic conditions were kept constant for 2 min (flow rate 0.48 mL min-1) and then initial conditions were restored within 0.1 min, kept for 3 min and then the flow rate decreased to 0.2 mL min-1 for the last minute. The injection volume was set to 5 µL.

The QTOF system was equipped with an electrospray ionization interface (ESI), operating in positive and negative mode, with the following operation parameters: capillary voltage 2500 V (PI) and 3500 (NI); end plate offset, 500 V; nebulizer pressure 2 bar; drying gas 8 L min−1 and gas temperature 200 °C.Full scan mass spectra were recorded over the range 50–1000 m/z with a scan rate of 2 spectra s-1. MS/MS experiments were conducted using AutoMS acquisition mode (data-dependent acquisition) using an inclusion list of 73 pairs. The collision energy applied was set to five predefined values, 10, 20, 30, 40 and 50 eV for each MS/MS experiment. A QTOF external calibration was performed daily with the manufacturer's solution. The instrument provided a typical resolving power (FWHM) between 36,000-40,000 at m/z 226.1593, 430.9137 and 702.8636. Mass spectra acquisition and data analysis was processed with DataAnalysis 4.1 and TargetAnalysis 1.3 (Bruker Daltonics, Bremen, Germany).

S1

Section S3. Table of Structurally Related and Unrelated Pairs

Table S1. Structurally Related and Unrelated Pairs. Related pairs are indicated as “True pair”, while unrelated pairs are indicated as “False pair” under the column Type. Transformation types were assessed manually by comparing the affected functional groups of the parent compound and the transformation product. LogD and TanimotoDissimilarity values were calculated with JChem for Excel. Formula differences were calculated with RMassBank.

Transformation Product / Parent Compound / Type / TP CAS / TP logD (pH7) / TP SMILES / TP Formula / TP m/z / Parent CAS / Parent logD (pH7) / Parent SMILES / Parent Formula / Parent m/z / Ionization / Mass Difference / Formula Difference / Tanimoto Dissimilarity / Transformation
N4-Acetyl-Sulfathiazol / Sulfathiazol / True pair / 127-76-4 / 0.69 / CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1 / C11H11N3O3S2 / 297.0242 / 72-14-0 / 0.69 / NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1 / C9H9N3O2S2 / 255.0136 / positive / 42.0106 / C2H2O1 / 0.29 / acetylation
4-Acetamidoantipyrin (=N-Acetyl-4-Aminoantipyrin 4-AAA) / Aminopyrine / True pair / 83-15-8 / 0.15 / CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1 / C13H15N3O2 / 245.1164 / 58-15-1 / 1.15 / CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1 / C13H17N3O / 231.1372 / positive / 13.9792 / H-2O1 / 0.28 / multiple
N4-Acetyl-Sulfadimethoxin / Sulfadimethoxin / True pair / 24341-30-8 / 1.00 / COC1=CC(OC)=NC(NS(=O)(=O)C2=CC=C(NC(C)=O)C=C2)=N1 / C14H16N4O5S / 352.0841 / 122-11-2 / 0.97 / COC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N1 / C12H14N4O4S / 310.0736 / positive / 42.0105 / C2H2O1 / 0.28 / acetylation
N4-Acetyl-Sulfamethazin / Sulfamethazin / True pair / 100-90-3 / 0.41 / CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=NC(C)=CC(C)=N1 / C14H16N4O3S / 320.0943 / 57-68-1 / 0.39 / CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1 / C12H14N4O2S / 278.0837 / positive / 42.0106 / C2H2O1 / 0.25 / acetylation
N4-Acetyl-Sulfadiazin / Sulfadiazin / True pair / 127-74-2 / 0.15 / CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1 / C12H12N4O3S / 292.063 / 68-35-9 / 0.13 / NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1 / C10H10N4O2S / 250.0524 / positive / 42.0106 / C2H2O1 / 0.27 / acetylation
Dimethenamid-OXA / Dimethenamid / True pair / 380412-59-9 / -1.04 / COCC(C)N(C(=O)C(O)=O)c1c(C)csc1C / C12H17N1O4S1 / 271.0878 / 87674-68-8 / 2.92 / COCC(C)N(C(=O)CCl)C1=C(C)SC=C1C / C12H18ClNO2S / 275.0747 / positive / -3.9869 / H-1O2Cl-1 / 0.45 / OXA
Dimethenamid-ESA / Dimethenamid / True pair / 205939-58-8 / -0.79 / COCC(C)N(C(=O)CS(O)(=O)=O)c1c(C)csc1C / C12H19N1O5S2 / 321.0705 / 87674-68-8 / 2.92 / COCC(C)N(C(=O)CCl)C1=C(C)SC=C1C / C12H18ClNO2S / 275.0747 / positive / 45.9958 / H1O3S1Cl-1 / 0.53 / ESA
Metolachlor-OXA / Metolachlor / True pair / 152019-73-3 / -0.46 / CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)C(O)=O / C15H21N1O4 / 279.1471 / 51218-45-2 / 3.45 / CCC1=C(N(C(C)COC)C(=O)CCl)C(C)=CC=C1 / C15H22ClNO2 / 283.1339 / positive / -3.9868 / H-1O2Cl-1 / 0.44 / OXA
Prometon-Hydroxy-Desisopropyl / Prometon / True pair / 19988-24-0 / -0.64 / CC(C)NC1=NC(=O)N=C(N)N1 / C6H11N5O / 169.0964 / 1610-18-0 / 2.22 / COC1=NC(NC(C)C)=NC(NC(C)C)=N1 / C10H19N5O / 225.159 / positive / -56.0626 / C-4H-8 / 0.49 / multiple
Atrazin-desethyl-2-hydroxy (=Prometon-Hydroxy-Desisopropyl) / Atrazin / True pair / 19988-24-0 / -0.64 / CC(C)NC1=NC(=O)N=C(N)N1 / C6H11N5O / 169.0964 / 1912-24-9 / 2.20 / CCNC1=NC(NC(C)C)=NC(Cl)=N1 / C8H14Cl1N5 / 215.0938 / positive / -45.9974 / C-2H-3O1Cl-1 / 0.40 / multiple
Atrazin-2-Hydroxy / Atrazine / True pair / 2163-68-0 / 0.00 / CCNC1=NC(=O)N=C(NC(C)C)N1 / C8H15N5O / 197.1277 / 1912-24-9 / 2.20 / CCNC1=NC(NC(C)C)=NC(Cl)=N1 / C8H14Cl1N5 / 215.0938 / positive / -17.9661 / H1O1Cl-1 / 0.26 / dehalogenation
Irgarol-descyclopropyl / Irgarol / True pair / 30125-65-6 / 2.19 / S(C)-c(nc(n1)N)nc1NC(C)(C)C / C8H15N5S / 213.1048 / 28159-98-0 / 2.97 / CSC1=NC(NC(C)(C)C)=NC(NC2CC2)=N1 / C11H19N5S1 / 253.1361 / positive / -40.0313 / C-3H-4 / 0.29 / descyclopropyl
Isoproturon-didemethyl = 1-(4-Isoprophenyl)urea / Isoproturon / True pair / 56046-17-4 / 2.12 / CC(C)C1=CC=C(NC(N)=O)C=C1 / C10H14N2O / 178.1106 / 34123-59-6 / 2.57 / CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 / C12H18N2O1 / 206.1419 / positive / -28.0313 / C-2H-4 / 0.26 / didesmethyl
Atrazin-Desisopropyl / Atrazine / True pair / 1007-28-9 / 1.12 / CCNC1=NC(Cl)=NC(N)=N1 / C5H8ClN5 / 173.0468 / 1912-24-9 / 2.20 / CCNC1=NC(NC(C)C)=NC(Cl)=N1 / C8H14Cl1N5 / 215.0938 / positive / -42.047 / C-3H-6 / 0.34 / desisopropyl
Diuron-desdimethyl = 1-(3,4-Dichlorophenyl)urea / Diuron / True pair / 08.02.2327 / 2.09 / NC(=O)NC1=CC(Cl)=C(Cl)C=C1 / C7H6Cl2N2O / 203.9857 / 330-54-1 / 2.53 / CN(C)C(=O)NC1=CC(Cl)=C(Cl)C=C1 / C9H10Cl2N2O1 / 232.017 / positive / -28.0313 / C-2H-4 / 0.27 / didesmethyl
Diuron-desmonomethyl (DCPMU) = 1-(3,4-Dichlorophenyl)-3-methylurea / Diuron / True pair / 3567-62-2 / 2.31 / CNC(=O)NC1=CC(Cl)=C(Cl)C=C1 / C8H8Cl2N2O / 218.0014 / 330-54-1 / 2.53 / CN(C)C(=O)NC1=CC(Cl)=C(Cl)C=C1 / C9H10Cl2N2O1 / 232.017 / positive / -14.0156 / C-1H-2 / 0.14 / demethylation
Ethofumesat-2-keto / Ethofumesate / True pair / 26244-33-7 / 1.64 / CC1(C)C(=O)OC2=C1C=C(OS(C)(=O)=O)C=C2 / C11H12O5S / 256.0405 / 26225-79-6 / 2.34 / CCOC1OC2=C(C=C(OS(C)(=O)=O)C=C2)C1(C)C / C13H18O5S1 / 286.0875 / positive / -30.047 / C-2H-6 / 0.20 / deethylation
Metamitron-desamino / Metamitron / True pair / 36993-94-9 / 0.02 / CC1=NC(=O)C(=NN1)C1=CC=CC=C1 / C10H9N3O1 / 187.0746 / 41394-05-2 / 0.44 / CC1=NN=C(C(=O)N1N)C1=CC=CC=C1 / C10H10N4O1 / 202.0855 / positive / -15.0109 / H-1N-1 / 0.17 / desamino
Simazin-2-hydroxy / Simazin / True pair / 03.11.2599 / -0.42 / CCNC1=NC(=O)N=C(NCC)N1 / C7H13N5O1 / 183.112 / 122-34-9 / 1.78 / CCNC1=NC(NCC)=NC(Cl)=N1 / C7H12ClN5 / 201.0781 / positive / -17.9661 / H1O1Cl-1 / 0.27 / dehalogenation
Terbutylazin-desethyl / Terbutylazine / True pair / 30125-63-4 / 1.82 / CC(C)(C)NC1=NC(N)=NC(Cl)=N1 / C7H12Cl1N5 / 201.0781 / 5915-41-3 / 2.48 / CCNC1=NC(NC(C)(C)C)=NC(Cl)=N1 / C9H16ClN5 / 229.1094 / positive / -28.0313 / C-2H-4 / 0.22 / deethylation
Terbutylazin-desethyl-2-hydroxy / Terbutylazine / True pair / 66753-06-8 / -0.36 / CC(C)(C)NC1=NC(=O)N=C(N)N1 / C7H13N5O1 / 183.112 / 5915-41-3 / 2.48 / CCNC1=NC(NC(C)(C)C)=NC(Cl)=N1 / C9H16ClN5 / 229.1094 / positive / -45.9974 / C-2H-3O1Cl-1 / 0.39 / multiple
Fipronil-sulfid / Fipronil / True pair / 120067-83-6 / 5.62 / NC1=C(SC(F)(F)F)C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N / C12H4Cl2F6N4S1 / 419.9438 / 120068-37-3 / 4.49 / NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F / C12H4Cl2F6N4O1S1 / 435.9387 / positive / -15.9949 / O-1 / 0.07 / sulfur reduction
Atenolol-desisopropyl / Atenolol / True pair / 81346-71-6 / -3.03 / NCC(O)COC1=CC=C(CC(N)=O)C=C1 / C11H16N2O3 / 224.1161 / 29122-68-7 / -2.14 / CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 / C14H22N2O3 / 266.163 / positive / -42.0469 / C-3H-6 / 0.27 / desisopropyl
2-Aminosulfonyl-benzoicacid-methylester (=Methyl-2-(aminosulfonyl)benzoate) / Metsulfuron-methyl / True pair / 57683-71-3 / 0.58 / COC(=O)C1=C(C=CC=C1)S(N)(=O)=O / C8H9NO4S / 215.0252 / 74223-64-6 / 1.05 / COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(C)=N1 / C14H15N5O6S / 381.0743 / positive / -166.0491 / C-6H-6N-4O-2 / 0.79 / urea derivative
DMSA (=N,N-Dimethylaminosulfanilid) / Dichlofluanid / True pair / 4710-17-2 / 0.34 / CN(C)S(=O)(=O)NC1=CC=CC=C1 / C8H12N2O2S / 200.0619 / 1085-98-9 / 3.22 / CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 / C9H11Cl2FN2O2S2 / 331.9623 / positive / -131.9004 / C-1H1S-1Cl-2F-1 / 0.61 / N-(dichloromethyl)sulfanylaniline derivative
Betamethason-21-acetat / Betamethason / True pair / 987-24-6 / 2.12 / C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COC(C)=O / C24H31FO6 / 434.2105 / 378-44-9 / 1.68 / C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO / C22H29FO5 / 392.1999 / positive / 42.0106 / C2H2O1 / 0.21 / acetylation
Guanylurea / Metformin / True pair / 141-83-3 / -2.06 / NC(N)=NC(N)=O / C2H6N4O / 102.0542 / 657-24-9 / -3.66 / CN(C)C(=N)N=C(N)N / C4H11N5 / 129.1014 / positive / -27.0472 / C-2H-5N-1O1 / 0.73 / oxidation
Dexamethason-21-acetat / Dexamethason / True pair / 1177-87-3 / 2.12 / C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COC(C)=O / C24H31FO6 / 434.2105 / 50-02-2 / 1.68 / C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO / C22H29FO5 / 392.1999 / positive / 42.0106 / C2H2O1 / 0.21 / acetylation
Pheniramine-N-oxide / Pheniramine / True pair / 12656-98-3 / 1.85 / C[N+](C)(CCC(c1ccccc1)c2ccccn2)[O-] / C16H20N2O / 256.1576 / 86-21-5 / 0.53 / CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2 / C16H20N2 / 240.1626 / positive / 15.995 / O1 / 0.25 / n-oxidation
Chlorothiazid / Hydrochlorothiazide / True pair / 58-94-6 / -0.45 / NS(=O)(=O)C1=CC2=C(NC=NS2(=O)=O)C=C1Cl / C7H6ClN3O4S2 / 294.9488 / 58-93-5 / -0.58 / NS(=O)(=O)C1=CC2=C(NCNS2(=O)=O)C=C1Cl / C7H8ClN3O4S2 / 296.9645 / positive / -2.0157 / H-2 / 0.13 / hydrogenation
2-Amino-4-methoxy-6-methyl-1,3,5 triazin / Thifensulfuron-methyl / True pair / 1668-54-8 / 0.59 / COC1=NC(N)=NC(C)=N1 / C5H8N4O / 140.0698 / 79277-27-3 / 1.03 / COC(=O)C1=C(C=CS1)S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 / C12H13N5O6S2 / 387.0307 / positive / -246.9609 / C-7H-5N-1O-5S-2 / 0.80 / multiple
2-Amino-4-methoxy-6-methyl-1,3,5 triazin / Metsulfuron-methyl / True pair / 1668-54-8 / 0.59 / COC1=NC(N)=NC(C)=N1 / C5H8N4O / 140.0698 / 74223-64-6 / 1.05 / COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(C)=N1 / C14H15N5O6S / 381.0743 / positive / -241.0045 / C-9H-7N-1O-5S-1 / 0.80 / multiple
4-Isopropylanilin / Isoproturon / True pair / 99-88-7 / 2.39 / CC(C)C1=CC=C(N)C=C1 / C9H13N / 135.1048 / 34123-59-6 / 2.57 / CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 / C12H18N2O1 / 206.1419 / positive / -71.0371 / C-3H-5N-1O-1 / 0.57 / urea derivative
Metolachlor-Morpholinon / Metolachlor / True pair / 120375-14-6 / 2.62 / CCC1=CC=CC(C)=C1N1C(C)COCC1=O / C14H19N1O2 / 233.1416 / 51218-45-2 / 3.45 / CCC1=C(N(C(C)COC)C(=O)CCl)C(C)=CC=C1 / C15H22ClNO2 / 283.1339 / positive / -49.9923 / C-1H-3Cl-1 / 0.24 / Rearrangement
2,6-Dichlorbenzamid / Dichlobenil / True pair / 2008-58-4 / 2.03 / NC(=O)C1=C(Cl)C=CC=C1Cl / C7H5Cl2NO / 188.9748 / 1194-65-6 / 3.04 / ClC1=CC=CC(Cl)=C1C#N / C7H3Cl2N / 170.9643 / positive / 18.0105 / H2O1 / 0.18 / hydration
Metribuzin-Desamino (DA) / Metribuzin / True pair / 35045-02-4 / 1.33 / CSC1=NC(=O)C(=NN1)C(C)(C)C / C8H13N3OS / 199.0779 / 21087-64-9 / 1.96 / CSC1=NN=C(C(=O)N1N)C(C)(C)C / C8H14N4O1S1 / 214.0888 / positive / -15.0109 / H-1N-1 / 0.23 / desamino
Metribuzin-Diketo (DK) / Metribuzin / True pair / 56507-37-0 / 0.64 / CC(C)(C)C1=NNC(=O)N(N)C1=O / C7H12N4O2 / 184.096 / 21087-64-9 / 1.96 / CSC1=NN=C(C(=O)N1N)C(C)(C)C / C8H14N4O1S1 / 214.0888 / positive / -29.9928 / C-1H-2O1S-1 / 0.28 / diketo
Ranitidin-S-oxid / Ranitidine / True pair / 73851-70-4 / -1.17 / CN\C(NCCS(=O)CC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O / C13H22N4O4S / 330.1362 / 66357-35-5 / 0.13 / CN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O / C13H22N4O3S / 314.1413 / positive / 15.9949 / O1 / 0.08 / sulphoxidation
Ranitidin-N-oxid / Ranitidine / True pair / 73857-20-2 / -0.13 / CN\C(NCCSCC1=CC=C(C[N+](C)(C)[O-])O1)=C/[N+]([O-])=O / C13H22N4O4S / 330.1362 / 66357-35-5 / 0.13 / CN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O / C13H22N4O3S / 314.1413 / positive / 15.9949 / O1 / 0.22 / n-oxidation
2-Aminobenzimidazol / Carbendazim / True pair / 934-32-7 / 0.14 / NC1=NC2=C(N1)C=CC=C2 / C7H7N3 / 133.064 / 10605-21-7 / 1.80 / COC(=O)NC1=NC2=C(N1)C=CC=C2 / C9H9N3O2 / 191.0695 / positive / -58.0055 / C-2H-2O-2 / 0.46 / carbamyl derivative
Propazine-2-hydroxy (=Prometon-Hydroxy) / Prometon / True pair / 7374-53-0 / 0.41 / CC(C)NC1=NC(=O)N=C(NC(C)C)N1 / C9H17N5O / 211.1433 / 1610-18-0 / 2.22 / COC1=NC(NC(C)C)=NC(NC(C)C)=N1 / C10H19N5O / 225.159 / positive / -14.0157 / C-1H-2 / 0.25 / demethylation
Trinexapac-Säure / Trinexapac-ethyl / True pair / 104273-73-6 / -4.17 / OC(=O)C1CC(=O)C(C(=O)C2CC2)C(=O)C1 / C11H12O5 / 224.0685 / 95266-40-3 / -2.37 / CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1 / C13H16O5 / 252.0998 / positive / -28.0313 / C-2H-4 / 0.37 / deethylation
N4-Acetyl-Sulfamethoxazol / Sulfamethoxazole / True pair / 21312-10-7 / 0.10 / CC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1 / C12H13N3O4S / 295.0627 / 723-46-6 / 0.14 / CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1 / C10H11N3O3S1 / 253.0521 / positive / 42.0106 / C2H2O1 / 0.27 / acetylation
Isoproturon-monodemethyl = 1-(4-Isoprophenyl)-3-methylurea / Isoproturon / True pair / 34123-57-4 / 2.35 / CNC(=O)NC1=CC=C(C=C1)C(C)C / C11H16N2O / 192.1263 / 34123-59-6 / 2.57 / CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 / C12H18N2O1 / 206.1419 / positive / -14.0156 / C-1H-2 / 0.13 / demethylation
Atrazin-Desethyl / Atrazine / True pair / 6190-65-4 / 1.54 / CC(C)NC1=NC(N)=NC(Cl)=N1 / C6H10ClN5 / 187.0625 / 1912-24-9 / 2.20 / CCNC1=NC(NC(C)C)=NC(Cl)=N1 / C8H14Cl1N5 / 215.0938 / positive / -28.0313 / C-2H-4 / 0.23 / deethylation
Terbutylazin-2-hydroxy / Terbutylazin / True pair / 66753-07-9 / 0.28 / CCNC1=NC(=O)N=C(NC(C)(C)C)N1 / C9H17N5O / 211.1433 / 5915-41-3 / 2.48 / CCNC1=NC(NC(C)(C)C)=NC(Cl)=N1 / C9H16ClN5 / 229.1094 / positive / -17.9661 / H1O1Cl-1 / 0.26 / dehalogenation
3-Phnzyl Alkohol / Permethrin / True pair / 13826-35-2 / 2.71 / OCC1=CC=CC(OC2=CC=CC=C2)=C1 / C13H12O2 / 200.0837 / 52645-53-1 / 5.70 / CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC2=CC=CC=C2)=C1 / C21H20Cl2O3 / 390.0789 / positive / -189.9952 / C-8H-8O-1Cl-2 / 0.69 / ester cleavage
3-Phenoxybenzoesäure / Permethrin / True pair / 3739-38-6 / 0.11 / OC(=O)c1cccc(Oc2ccccc2)c1 / C13H10O3 / 214.063 / 52645-53-1 / 5.70 / CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC2=CC=CC=C2)=C1 / C21H20Cl2O3 / 390.0789 / positive / -176.0159 / C-8H-10Cl-2 / 0.70 / multiple
2,4-dimethylphenylformamid / Amitraz / True pair / 60397-77-5 / 2.19 / CC1=CC(C)=C(NC=O)C=C1 / C9H11NO / 149.0841 / 33089-61-1 / 2.72 / CN(C=NC1=C(C)C=C(C)C=C1)C=NC1=C(C)C=C(C)C=C1 / C19H23N3 / 293.1892 / positive / -144.1051 / C-10H-12N-2O1 / 0.80 / formamidine derivatibe
N-(2,4-dimethylphenyl)-N-methylformamidin / Amitraz / True pair / 33089-74-6 / 0.81 / CN=CNC1=CC=C(C)C=C1C / C10H14N2 / 162.1157 / 33089-61-1 / 2.72 / CN(C=NC1=C(C)C=C(C)C=C1)C=NC1=C(C)C=C(C)C=C1 / C19H23N3 / 293.1892 / positive / -131.0735 / C-9H-9N-1 / 0.76 / formamidine derivatibe
Norfluoxetin / Fluoxetin / True pair / 56161-73-0 / 1.16 / NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1 / C16H16F3NO / 295.1184 / 54910-89-3 / 1.50 / CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1 / C17H18F3NO / 309.134 / positive / -14.0156 / C-1H-2 / 0.09 / demethylation
Fenofibrinsäure / Fenofibrate / True pair / 42017-89-0 / 0.98 / CC(C)(OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1)C(O)=O / C17H15ClO4 / 318.0659 / 49562-28-9 / 5.28 / CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1 / C20H21Cl1O4 / 360.1128 / positive / -42.0469 / C-3H-6 / 0.37 / desisopropyl
N,N-Dimethylsulfamid / Dichlofluanid / True pair / 3984-14-3 / -1.54 / CN(C)S(N)(=O)=O / C2H8N2O2S / 124.0306 / 1085-98-9 / 3.22 / CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 / C9H11Cl2FN2O2S2 / 331.9623 / positive / -207.9317 / C-7H-3S-1Cl-2F-1 / 0.94 / cleavage
Metolachlor-ESA / Metolachlor / True pair / 171118-09-5 / -0.26 / CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CS(O)(=O)=O / C15H23N1O5S1 / 329.1297 / 51218-45-2 / 3.45 / CCC1=C(N(C(C)COC)C(=O)CCl)C(C)=CC=C1 / C15H22ClNO2 / 283.1339 / positive / 45.9958 / H1O3S1Cl-1 / 0.52 / ESA
Oseltamivir-carboxylat / Oseltamivir / True pair / 187227-45-8 / -1.84 / CCC(CC)O[C@@H]1C=C(C[C@H](N)[C@H]1NC(C)=O)C(O)=O / C14H24N2O4 / 284.1736 / 196618-13-0 / -1.07 / CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 / C16H28N2O4 / 312.2049 / positive / -28.0313 / C-2H-4 / 0.31 / deethylation
Flufenacet-ESA / Flufenacet / True pair / 201668-32-8 / -1.19 / CC(C)N(C(=O)CS(O)(=O)=O)C1=CC=C(F)C=C1 / C11H14F1NO4S1 / 275.0628 / 142459-58-3 / 3.22 / CC(C)N(C(=O)COC1=NN=C(S1)C(F)(F)F)C1=CC=C(F)C=C1 / C14H13F4N3O2S / 363.0665 / positive / -88.0037 / C-3H1F-3N-2O2 / 0.72 / ESA
Flufenacet-OXA / Flufenacet / True pair / 201668-31-7 / -1.52 / CC(C)N(C(=O)C(O)=O)C1=CC=C(F)C=C1 / C11H12F1N1O3 / 225.0801 / 142459-58-3 / 3.22 / CC(C)N(C(=O)COC1=NN=C(S1)C(F)(F)F)C1=CC=C(F)C=C1 / C14H13F4N3O2S / 363.0665 / positive / -137.9864 / C-3H-1F-3N-2O1S-1 / 0.72 / OXA
Propachlor-ESA / Propachlor / True pair / 123732-85-4 / -1.33 / CC(C)N(C(=O)CS(O)(=O)=O)C1=CC=CC=C1 / C11H15N1O4S1 / 257.0722 / 1918-16-7 / 2.39 / CC(C)N(C(=O)CCl)C1=CC=CC=C1 / C11H14ClNO / 211.0764 / positive / 45.9958 / H1O3S1Cl-1 / 0.62 / ESA
Propachlor-OXA / Propachlor / True pair / 70628-36-3 / -1.59 / CC(C)N(C(=O)C(O)=O)C1=CC=CC=C1 / C11H13N1O3 / 207.0895 / 1918-16-7 / 2.39 / CC(C)N(C(=O)CCl)C1=CC=CC=C1 / C11H14ClNO / 211.0764 / positive / -3.9869 / H-1O2Cl-1 / 0.54 / OXA
Chloridazon-desphenyl / Chloridazon / True pair / 6339-19-1 / -0.78 / NC1=C(Cl)C(=O)NN=C1 / C4H4ClN3O / 145.0043 / 1698-60-8 / 1.11 / NC1=C(Cl)C(=O)N(N=C1)C1=CC=CC=C1 / C10H8Cl1N3O1 / 221.0356 / positive / -76.0313 / C-6H-4 / 0.66 / multiple
Atenololsäure (Metoprololsäure) / Atenolol / True pair / 56392-14-4 / -1.24 / CC(C)NCC(O)COC1=CC=C(CC(O)=O)C=C1 / C14H21N1O4 / 267.1471 / 29122-68-7 / -2.14 / CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 / C14H22N2O3 / 266.163 / positive / 0.9841 / H-1N-1O1 / 0.23 / amide hydrolysis
Atenololsäure (Metoprololsäure) / Metoprolol / True pair / 56392-14-4 / -1.24 / CC(C)NCC(O)COC1=CC=C(CC(O)=O)C=C1 / C14H21N1O4 / 267.1471 / 37350-58-6 / -0.81 / COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 / C15H25NO3 / 267.1834 / positive / -0.0363 / C-1H-4O1 / 0.32 / oxidation
Chloridazon-methyl-desphenyl / Chloridazon / True pair / 17254-80-7 / -0.55 / CN1N=CC(N)=C(Cl)C1=O / C5H6ClN3O / 159.0199 / 1698-60-8 / 1.11 / NC1=C(Cl)C(=O)N(N=C1)C1=CC=CC=C1 / C10H8Cl1N3O1 / 221.0356 / positive / -62.0157 / C-5H-2 / 0.65 / desphenyl
Metazachlor-OXA / Metazachlor / True pair / 1231244-60-2 / -1.05 / Cc1cccc(C)c1N(Cn1cccn1)C(=O)C(O)=O / C14H15N3O3 / 273.1113 / 67129-08-2 / 2.98 / CC1=CC=CC(C)=C1N(CN1C=CC=N1)C(=O)CCl / C14H16ClN3O / 277.0982 / positive / -3.9869 / H-1O2Cl-1 / 0.42 / OXA
2',2'-Difluorodeoxyuridin / Gemcitabine / True pair / 114248-23-6 / -1.08 / C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)(F)F / C9H10F2N2O5 / 264.0558 / 95058-81-4 / -1.47 / NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)C1(F)F / C9H11F2N3O4 / 263.0718 / positive / 0.984 / H-1N-1O1 / 0.16 / amide hydrolysis
Dimethachlor-ESA / Dimethachlor / True pair / -1.12 / COCCN(C(=O)CS(O)(=O)=O)c1c(C)cccc1C / C13H19NO5S / 301.0984 / 50563-36-5 / 2.59 / COCCN(C(=O)CCl)C1=C(C)C=CC=C1C / C13H18ClNO2 / 255.1026 / positive / 45.9958 / H1O3S1Cl-1 / 0.55 / ESA
Dimethachlor-OXA / Dimethachlor / True pair / 1086384-49-7 / -1.36 / COCCN(C(=O)C(O)=O)c1c(C)cccc1C / C13H17NO4 / 251.1158 / 50563-36-5 / 2.59 / COCCN(C(=O)CCl)C1=C(C)C=CC=C1C / C13H18ClNO2 / 255.1026 / positive / -3.9868 / H-1O2Cl-1 / 0.47 / OXA
4-Aminopyrin (=4-Aminoantipyrin 4-AA) / Aminopyrine / True pair / 83-07-8 / 0.33 / CN1N(C(=O)C(N)=C1C)C1=CC=CC=C1 / C11H13N3O1 / 203.1059 / 58-15-1 / 1.15 / CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1 / C13H17N3O / 231.1372 / positive / -28.0313 / C-2H-4 / 0.32 / didesmethyl
Carbamazepin-10,11-epoxid / Carbamazepine / True pair / 36507-30-9 / 1.97 / NC(=O)N1C2=C(C=CC=C2)C2OC2C2=C1C=CC=C2 / C15H12N2O2 / 252.0899 / 298-46-4 / 2.77 / NC(=O)N1C2=C(C=CC=C2)C=CC2=C1C=CC=C2 / C15H12N2O / 236.095 / positive / 15.9949 / O1 / 0.11 / epoxidation
Iminostilben / Carbamazepine / True pair / 256-96-2 / 3.78 / N1C2=C(C=CC=C2)C=CC2=C1C=CC=C2 / C14H11N1 / 193.0891 / 298-46-4 / 2.77 / NC(=O)N1C2=C(C=CC=C2)C=CC2=C1C=CC=C2 / C15H12N2O / 236.095 / positive / -43.0059 / C-1H-1N-1O-1 / 0.35 / urea derivative
N-Desvenlafaxin / Venlafaxin / True pair / 149289-30-5 / -0.30 / CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1 / C16H25N1O2 / 263.1885 / 93413-69-5 / 0.84 / COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / positive / -14.0157 / C-1H-2 / 0.17 / demethylation
4-Formylaminoantipyrin (4-FAA) / Aminopyrine / True pair / 1672-58-8 / 0.11 / CN1N(C(=O)C(NC=O)=C1C)C1=CC=CC=C1 / C12H13N3O2 / 231.1008 / 58-15-1 / 1.15 / CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1 / C13H17N3O / 231.1372 / positive / -0.0364 / C-1H-4O1 / 0.30 / oxidation
O-Desvenlafaxin / Venlafaxin / True pair / 93413-62-8 / 0.69 / CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1 / C16H25N1O2 / 263.1885 / 93413-69-5 / 0.84 / COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / positive / -14.0157 / C-1H-2 / 0.15 / demethylation
N,O-Didesvenlafaxin / Venlafaxin / True pair / 135308-74-6 / -0.43 / CNCC(C1=CC=C(O)C=C1)C1(O)CCCCC1 / C15H23N1O2 / 249.1729 / 93413-69-5 / 0.84 / COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / positive / -28.0313 / C-2H-4 / 0.29 / didesmethyl
D617 / Verapamil / True pair / 34245-14-2 / -0.10 / CNCCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C=C1 / C17H26N2O2 / 290.1994 / 152-11-4 / 2.42 / COC1=CC=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1OC / C27H38N2O4 / 454.2832 / positive / -164.0838 / C-10H-12O-2 / 0.62 / tertiary amine cleavage
N,N-Didesvenlafaxin / Venlafaxin / True pair / 93413-77-5 / -0.41 / COC1=CC=C(C=C1)C(CN)C1(O)CCCCC1 / C15H23N1O2 / 249.1729 / 93413-69-5 / 0.84 / COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / positive / -28.0313 / C-2H-4 / 0.25 / didesmethyl
Carbamazepin-10,11-dihydro-10,11-dihydroxy / Carbamazepine / True pair / 58955-93-4 / 0.81 / NC(=O)N1C2=C(C=CC=C2)[C@H](O)[C@@H](O)C2=C1C=CC=C2 / C15H14N2O3 / 270.1004 / 298-46-4 / 2.77 / NC(=O)N1C2=C(C=CC=C2)C=CC2=C1C=CC=C2 / C15H12N2O / 236.095 / positive / 34.0054 / H2O2 / 0.35 / dihydroxylation
Diazoxon / Diazinon / True pair / 962-58-3 / 3.38 / CCOP(=O)(OCC)OC1=NC(=NC(C)=C1)C(C)C / C12H21N2O4P1 / 288.1239 / 333-41-5 / 4.19 / CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C / C12H21N2O3P1S1 / 304.1011 / positive / -15.9772 / O1S-1 / 0.00 / desulphuration
Azoxystrobinsäure / Azoxystrobin / True pair / 1185255-09-7 / 0.55 / CO\C=C(\C(O)=O)c1ccccc1Oc1cc(Oc2ccccc2C#N)ncn1 / C21H15N3O5 / 389.1012 / 131860-33-8 / 4.22 / CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=NC=NC(OC2=C(C=CC=C2)C#N)=C1 / C22H17N3O5 / 403.1168 / positive / -14.0156 / C-1H-2 / 0.21 / demethylation
Pyrimidinol / Diazinon / True pair / 2814-20-2 / 0.59 / CC(C)C1=NC(=O)C=C(C)N1 / C8H12N2O1 / 152.095 / 333-41-5 / 4.19 / CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C / C12H21N2O3P1S1 / 304.1011 / positive / -152.0061 / C-4H-9O-2P-1S-1 / 0.67 / multiple
AMDOPH / Aminopyrine / True pair / 519-65-3 / 0.09 / CN(C)C(=O)C(=O)N(N(C)C(C)=O)C1=CC=CC=C1 / C13H17N3O3 / 263.127 / 58-15-1 / 1.15 / CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1 / C13H17N3O / 231.1372 / positive / 31.9898 / O2 / 0.67 / oxidation
Valsartansäure / Valsartan / True pair / 164265-78-5 / 0.29 / OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C14H10N4O2 / 266.0804 / 137862-53-4 / 2.66 / CCCCC(=O)N(CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1)[C@@H](C(C)C)C(O)=O / C24H29N5O3 / 435.227 / positive / -169.1466 / C-10H-19N-1O-1 / 0.61 / multiple
Valsartansäure / Losartan / True pair / 164265-78-5 / 0.29 / OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C14H10N4O2 / 266.0804 / 114798-26-4 / 5.06 / CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C22H23ClN6O / 422.1622 / positive / -156.0818 / C-8H-13N-2O1Cl-1 / 0.61 / multiple
Valsartansäure / Candesartan / True pair / 164265-78-5 / 0.29 / OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C14H10N4O2 / 266.0804 / 139481-59-7 / 2.05 / CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C24H20N6O3 / 440.1597 / positive / -174.0793 / C-10H-10N-2O-1 / 0.61 / multiple
Valsartansäure / Irbesartan / True pair / 164265-78-5 / 0.29 / OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C14H10N4O2 / 266.0804 / 138402-11-6 / 5.47 / CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 / C25H28N6O / 428.2325 / positive / -162.1521 / C-11H-18N-2O1 / 0.62 / multiple
1-Methyl-Benzotriazol / Benzotriazol / True pair / 13351-73-0 / 1.42 / CN1N=NC2=CC=CC=C12 / C7H7N3 / 133.064 / 95-14-7 / 1.26 / N1N=C2C=CC=CC2=N1 / C6H5N3 / 119.0483 / positive / 14.0157 / C1H2 / 0.33 / methylation
4-Amino-6-chloro-1,3-benzenedisulfonamid / Hydrochlorothiazide / True pair / 121-30-2 / -1.04 / NC1=C(C=C(C(Cl)=C1)S(N)(=O)=O)S(N)(=O)=O / C6H8ClN3O4S2 / 284.9645 / 58-93-5 / -0.58 / NS(=O)(=O)C1=CC2=C(NCNS2(=O)=O)C=C1Cl / C7H8ClN3O4S2 / 296.9645 / positive / -12 / C-1 / 0.15 / Rearrangement
Pargyline-N-Oxid / Pargyline / True pair / 74796-01-3 / 1.02 / C[N+]([O-])(CC#C)CC1=CC=CC=C1 / C11H13NO / 175.0997 / 555-57-7 / 1.24 / CN(CC#C)CC1=CC=CC=C1 / C11H13N / 159.1048 / positive / 15.9949 / O1 / 0.36 / n-oxidation
Normianserin / Mianserin / True pair / 76134-77-5 / 1.62 / C1CN2C(CN1)C3=CC=CC=C3CC4=CC=CC=C42 / C17H18N2 / 250.147 / 24219-97-4 / 3.57 / CN1CCN2C(C1)C1=C(CC3=C2C=CC=C3)C=CC=C1 / C18H20N2 / 264.1626 / positive / -14.0156 / C-1H-2 / 0.19 / demethylation
Mianserin-N-Oxide / Mianserin / True pair / 62510-46-7 / 2.71 / C[N+]1([O-])CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C21 / C18H20N2O / 280.1576 / 24219-97-4 / 3.57 / CN1CCN2C(C1)C1=C(CC3=C2C=CC=C3)C=CC=C1 / C18H20N2 / 264.1626 / positive / 15.995 / O1 / 0.25 / n-oxidation
Lidocaine-N-Oxide / Lidocaine / True pair / 2903-45-9 / 1.72 / CC[N+]([O-])(CC)CC(=O)NC1=C(C)C=CC=C1C / C14H22N2O2 / 250.1681 / 137-58-6 / 2.02 / CCN(CC)CC(=O)NC1=C(C)C=CC=C1C / C14H22N2O / 234.1732 / positive / 15.9949 / O1 / 0.28 / n-oxidation
Nornicotine / Nicotine / True pair / 5746-86-1 / -1.97 / C1CNC(C1)C1=CC=CN=C1 / C9H12N2 / 148.1 / 54-11-5 / -0.42 / CN1CCC[C@H]1C1=CN=CC=C1 / C10H14N2 / 162.1157 / positive / -14.0157 / C-1H-2 / 0.26 / demethylation
Nordeprenyl / Deprenyl / True pair / 18913-84-3 / 0.43 / CC(CC1=CC=CC=C1)NCC#C / C12H15N / 173.1204 / 14611-51-9 / 1.17 / C[C@H](CC1=CC=CC=C1)N(C)CC#C / C13H17N / 187.1361 / positive / -14.0157 / C-1H-2 / 0.24 / demethylation
Cotinine / Nicotine / True pair / 486-56-6 / 0.21 / CN1C(CCC1=O)C1=CN=CC=C1 / C10H12N2O / 176.095 / 54-11-5 / -0.42 / CN1CCC[C@H]1C1=CN=CC=C1 / C10H14N2 / 162.1157 / positive / 13.9793 / H-2O1 / 0.14 / oxidation
Tramadol N-Oxide / Tramadol / True pair / 147441-56-3 / 1.33 / COC1=CC=CC(=C1)C1(O)CCCCC1C[N+](C)(C)[O-] / C16H25NO3 / 279.1834 / 27203-92-5 / 0.24 / COC1=CC(=CC=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C / C16H25NO2 / 263.1885 / positive / 15.9949 / O1 / 0.24 / n-oxidation
Gabapentin Related Compound E / Gabapentin / True pair / 67950-95-2 / -2.34 / OC(=O)CC1(CCCCC1)C(O)=O / C9H14O4 / 186.0892 / 60142-96-3 / -1.27 / NCC1(CC(O)=O)CCCCC1 / C9H17NO2 / 171.1259 / positive / 14.9633 / H-3O2N-1 / 0.43 / amine oxidation
1-Hydroxy-Benzotriazol / Benzotriazol / True pair / 2592-95-2 / 0.27 / N.ON1N=NC2=C1C=CC=C2 / C6H5N3O / 152.0698 / 95-14-7 / 1.26 / N1N=C2C=CC=CC2=N1 / C6H5N3 / 119.0483 / positive / 33.0215 / O1 / 0.23 / oxidation
4-Hydroxy-Benzotriazol / Benzotriazol / True pair / 26725-51-9 / -0.27 / O=C1C=CC=C2NNN=C12 / C6H5N3O / 135.0433 / 95-14-7 / 1.26 / N1N=C2C=CC=CC2=N1 / C6H5N3 / 119.0483 / positive / 15.995 / O1 / 0.25 / oxidation
Benzoylecgonin / Cocaine / True pair / 519-09-5 / -0.60 / CN1C2CCC1[C@H]([C@H](C2)OC(=O)C1=CC=CC=C1)C(O)=O / C16H19NO4 / 289.1314 / 50-36-2 / 0.44 / COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C / C17H21NO4 / 303.1471 / positive / -14.0157 / C-1H-2 / 0.28 / demethylation
EDDP (2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidin) / Methadon / True pair / 30223-73-5 / 2.04 / C\C=C1/N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1 / C20H23N / 277.183 / 76-99-3 / 2.90 / CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 / C21H27NO / 309.2093 / positive / -32.0263 / C-1H-4O-1 / 0.23 / Rearrangement
Methiocarb-sulfoxide / Methiocarb / True pair / 01.10.2635 / 1.23 / CNC(=O)OC1=CC(C)=C(C(C)=C1)S(C)=O / C11H15NO3S / 241.0773 / 2032-65-7 / 3.13 / CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 / C11H15NO2S / 225.0823 / positive / 15.995 / O1 / 0.13 / sulphoxidation
Thiacloprid-amide / Thiacloprid / True pair / 676228-91-4 / 1.06 / NC(=O)N=C1SCCN1CC1=CN=C(Cl)C=C1 / C10H11ClN4OS / 270.0342 / 111988-49?-9 / 2.06 / C1CSC(=NC#N)N1CC2=CN=C(C=C2)Cl / C10H9ClN4S / 252.0236 / positive / 18.0106 / H2O1 / 0.21 / oxidation
Imidacloprid-urea / Imidacloprid / True pair / 120868-66-8 / 0.47 / ClC1=NC=C(CN2CCNC2=O)C=C1 / C9H10ClN3O / 211.0512 / 138261-41-3 / -3.74 / [O-][N+](=O)NC1=NCCN1CC1=CN=C(Cl)C=C1 / C9H10ClN5O2 / 255.0523 / positive / -44.0011 / N-2O-1 / 0.41 / Nitroguanidine derivative
2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidin / Capecitabin / True pair / 161599-46-8 / -0.67 / CC1OC(C(OC(C)=O)C1OC(C)=O)N1C=C(F)C(N)=NC1=O / C13H16FN3O6 / 329.1023 / 154361-50-9 / 0.34 / CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O / C15H22FN3O6 / 359.1493 / positive / -30.047 / C-2H-6 / 0.46 / multiple
Imidacloprid-desnitro / Imidacloprid / True pair / 115970-17-7 / -1.72 / NC1=NCCN1CC1=CN=C(Cl)C=C1 / C9H11ClN4 / 210.0672 / 138261-41-3 / -3.74 / [O-][N+](=O)NC1=NCCN1CC1=CN=C(Cl)C=C1 / C9H10ClN5O2 / 255.0523 / positive / -44.9851 / H1N-1O-2 / 0.22 / desnitro
1H-Benzotriazole-5-carboxylic acid / 4-Methyl-Benzotriazol / True pair / 23814-12-2 / -2.24 / OC(=O)C1=CC2=NNN=C2C=C1 / C7H5N3O2 / 163.0382 / 29878-31-7 / 1.77 / CC1=CC=CC2=NNN=C12 / C7H7N3 / 133.064 / positive / 29.9742 / H-2O2 / 0.53 / oxidation
1H-1,2,3-triazole-5-OH / 1H-1,2,3-triazole / True pair / 930-33-6 / -1.37 / O=C1NNC=N1 / C2H3N3O / 85.0276 / 288-36-8 / -0.50 / N1N=CC=N1 / C2H3N3 / 69.0327 / positive / 15.9949 / O1 / 0.39 / oxidation
Cetirizine N-Oxide / Cetirizine / True pair / 1076199-80-8 / -0.69 / OC(=O)COCC[N+]1([O-])CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1 / C21H25ClN2O4 / 404.1503 / 83881-51-0 / 0.81 / N1([C@@H](c2ccc(Cl)cc2)c2ccccc2)CCN(CCOCC(O)=O)CC1 / C21H25ClN2O3 / 388.1554 / positive / 15.9949 / O1 / 0.17 / n-oxidation
1-[(4-Chlorophenyl)phenylmethyl]piperazine / Cetirizine / True pair / 303-26-4 / 1.59 / ClC1=CC=C(C=C1)C(N1CCNCC1)C1=CC=CC=C1 / C17H19ClN2 / 286.1237 / 83881-51-0 / 0.81 / N1([C@@H](c2ccc(Cl)cc2)c2ccccc2)CCN(CCOCC(O)=O)CC1 / C21H25ClN2O3 / 388.1554 / positive / -102.0317 / C-4H-6O-3 / 0.58 / tertiary amine cleavage
3-[(4-chlorobenzoyl)amino]propanoic acid / Bezafibrate / True pair / 440341-75-3 / -1.71 / OC(=O)CCNC(=O)C1=CC=C(Cl)C=C1 / C10H10ClNO3 / 227.0349 / 41859-67-0 / 0.97 / CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O / C19H20ClNO4 / 361.1081 / positive / -134.0732 / C-9H-10O-1 / 0.72 / Rearrangement
Venlafaxine N-Oxide / Venlafaxine / True pair / 1094598-37-4 / 1.61 / OC1(C(C2=CC=C(OC)C=C2)C[N+](C)(C)[O-])CCCCC1 / C17H27NO3 / 293.1991 / 93413-69-5 / 0.84 / COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / positive / 15.9949 / O1 / 0.23 / n-oxidation
4'-Hydroxy Diclofenac / Diclofenac / True pair / 64118-84-9 / 0.89 / OC(=O)CC1=C(NC2=C(Cl)C=C(O)C=C2Cl)C=CC=C1 / C14H11Cl2NO3 / 311.0116 / 15307-86-5 / 1.37 / OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl / C14H11Cl2N1O2 / 295.0167 / positive / 15.9949 / O1 / 0.16 / oxidation
N-Bisdesmethyl Tramadol / Tramadol / True pair / 931115-27-4 / -0.88 / COC1=CC=CC(=C1)C1(O)CCCCC1CN / C14H21NO2 / 235.1572 / 27203-92-5 / 0.24 / COC1=CC(=CC=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C / C16H25NO2 / 263.1885 / positive / -28.0313 / C-2H-4 / 0.26 / didesmethyl
Amisulpride N-Oxide / Amisulpride / True pair / 71676-01-2 / -0.87 / CC[N+]1([O-])CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC / C17H27N3O5S / 385.1671 / 71675-85-9 / -0.08 / CCN1CCCC1CNC(=O)C1=C(OC)C=C(N)C(=C1)S(=O)(=O)CC / C17H27N3O4S / 369.1722 / positive / 15.9949 / O1 / 0.20 / n-oxidation
5-Hydroxy Diclofenac / Diclofenac / True pair / 69002-84-2 / 0.93 / OC(=O)CC1=C(NC2=C(Cl)C=CC=C2Cl)C=CC(O)=C1 / C14H11Cl2NO3 / 311.0116 / 15307-86-5 / 1.37 / OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl / C14H11Cl2N1O2 / 295.0167 / positive / 15.9949 / O1 / 0.16 / oxidation
N-desmethylpheniramine / Pheniramine / True pair / -0.31 / CNCCC(C1=CC=CC=C1)C2=CC=CC=N2 / C15H18N2 / 226.147 / 86-21-5 / 0.53 / CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2 / C16H20N2 / 240.1626 / positive / -14.0156 / C-1H-2 / 0.19 / demethylation
Clarithromycin N-Oxide / Clarithromycin / True pair / 118074-07-0 / 2.12 / [O-][N+](C)(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]2(C)OC)[C@@H]3O / C38H69NO14 / 763.4718 / 81103-11-9 / 1.84 / CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O)OC / C38H69NO13 / 747.4769 / positive / 15.9949 / O1 / 0.10 / n-oxidation
R-Deprenyl N-Oxide / Deprenyl / True pair / 366462-61-5 / 1.72 / CC(CC1=CC=CC=C1)[N+](C)([O-])CC#C / C13H17NO / 203.131 / 14611-51-9 / 1.17 / C[C@H](CC1=CC=CC=C1)N(C)CC#C / C13H17N / 187.1361 / positive / 15.9949 / O1 / 0.32 / n-oxidation
Kresoxim-methyl acid / Kresoxim-methyl / True pair / 1007364-30-8 / 0.73 / O=C(O)\C(=N\OC)c2ccccc2COc1ccccc1C / C17H17NO4 / 299.1158 / 143390-89-0 / 4.34 / CO\N=C(\C(=O)OC)C1=C(COC2=C(C)C=CC=C2)C=CC=C1 / C18H19NO4 / 313.1314 / positive / -14.0156 / C-1H-2 / 0.27 / demethylation
Norlidocaine / Lidocaine / True pair / 7728-40-7 / 0.52 / CCNCC(=O)NC1=C(C)C=CC=C1C / C12H18N2O / 206.1419 / 137-58-6 / 2.02 / CCN(CC)CC(=O)NC1=C(C)C=CC=C1C / C14H22N2O / 234.1732 / positive / -28.0313 / C-2H-4 / 0.30 / deethylation
Trimipramine N-Oxide / Trimipramine / True pair / 14171-70-1 / 3.63 / CC(CN1C2=CC=CC=C2CCC2=CC=CC=C12)C[N+](C)(C)[O-] / C20H26N2O / 310.2045 / 739-71-9 / 2.37 / CC(CN(C)C)CN1C2=CC=CC=C2CCC2=C1C=CC=C2 / C20H26N2 / 294.2096 / positive / 15.9949 / O1 / 0.23 / n-oxidation
N-Desmethyltramadol / Tramadol / True pair / 80456-81-1 / 0.10 / CN(C)CC1CCCCC1(O)C1=CC(O)=CC=C1 / C15H23NO2 / 249.1729 / 27203-92-5 / 0.24 / COC1=CC(=CC=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C / C16H25NO2 / 263.1885 / positive / -14.0156 / C-1H-2 / 0.16 / demethylation
Norclozapine / Clozapin / True pair / 6104-71-8 / -0.85 / ClC1=CC2=C(C=C1)N=C1C=CC=CC1=C(N2)N1CCNCC1 / C17H17ClN4 / 312.1142 / 5786-21-0 / 0.74 / CN1CCN(CC1)C1=C2C=CC=CC2=NC2=C(N1)C=C(Cl)C=C2 / C18H19ClN4 / 326.1298 / positive / -14.0156 / C-1H-2 / 0.16 / demethylation
Nordiazepam / Diazepam / True pair / 1088-11-5 / 3.21 / ClC1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1 / C15H11ClN2O / 270.056 / 439-14-5 / 3.08 / CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1 / C16H13ClN2O / 284.0716 / positive / -14.0156 / C-1H-2 / 0.19 / demethylation
Norfentanyl / Fentanyl / True pair / 1609-66-1 / -1.40 / CCC(=O)N(C1CC[NH2+]CC1)C1=CC=CC=C1 / C14H20N2O / 233.1654 / 437-38-7 / 2.05 / CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1 / C22H28N2O / 336.2202 / positive / -103.0548 / C-8H-8 / 0.59 / tertiary amine cleavage
Ecgonine-methyl-ester (EME) / Cocaine / True pair / 01.09.7143 / -2.24 / COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C / C10H17NO3 / 199.1208 / 50-36-2 / 0.44 / COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C / C17H21NO4 / 303.1471 / positive / -104.0263 / C-7H-4O-1 / 0.62 / ester cleavage
8-hydroxy Mirtazapine / Mirtazapine / True pair / 102335-57-9 / 2.76 / CN1CCN2C(C1)C1=CC=CC=C1CC1=CC(O)=CN=C21 / C17H19N3O / 281.1528 / 85650-52-8 / 3.04 / CN1CCN2C(C1)C1=C(CC3=C2N=CC=C3)C=CC=C1 / C17H19N3 / 265.1579 / positive / 15.9949 / O1 / 0.17 / oxidation
7-amino-flunitrazepam / Flunitrazepam / True pair / 34084-50-9 / 1.79 / CN1C2=CC=C(N)C=C2C(=NCC1=O)C1=CC=CC=C1F / C16H14FN3O / 283.1121 / 1622-62-4 / 2.55 / CN1C2=C(C=C(C=C2)[N+]([O-])=O)C(=NCC1=O)C1=C(F)C=CC=C1 / C16H12FN3O3 / 313.0863 / positive / -29.9742 / H2O-2 / 0.25 / nitro reduction
Prednisone / Prednisolone / True pair / 53-03-2 / 1.66 / C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO / C21H26O5 / 358.178 / 50-24-8 / 1.27 / C1[C@H]2[C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)[C@@H](O)C[C@@]2([C@](C(CO)=O)(O)C1)C / C21H28O5 / 360.1937 / positive / -2.0157 / H-2 / 0.07 / dehydrogenation
N-(2,4-dimethylphenyl)formamide / N'-(2,4-Dimethylphenyl)-N-methylformamidine / True pair / 60397-77-5 / 2.19 / Cc1ccc(NC=O)c(C)c1 / C9H11NO / 149.0841 / 33089-74-6 / 0.81 / C(=NC)Nc1c(cc(cc1)C)C / C10H14N2 / 162.1157 / positive / -13.0316 / C-1H-3N-1O1 / 0.41 / oxidation
N,N-Didesmethylvenlafaxine / N-Desmethylvenlafaxine / True pair / 93413-77-5 / -0.41 / COc1ccc(cc1)C(CN)C1(O)CCCCC1 / C15H23N1O2 / 249.1729 / 149289-30-5 / -0.30 / CNCC(C1=CC=C(C=C1)OC)C2(CCCCC2)O / C16H25N1O2 / 263.1885 / positive / -14.0156 / C-1H-2 / 0.10 / demethylation
Amphetamine / Nordeprenyl / True pair / 300-62-9 / -0.92 / CC(N)Cc1ccccc1 / C9H13N / 135.1048 / 18913-84-3 / 0.43 / CC(Cc1ccccc1)NCC#C / C12H15N / 173.1204 / positive / -38.0156 / C-3H-2 / 0.40 / secondary amine cleavage
4-chloro-N-methylaniline / 4-chloro-N,N-dimethylaniline / True pair / 932-96-7 / 2.05 / CNc1ccc(Cl)cc1 / C7H8ClN / 141.0345 / 698-69-1 / 2.68 / CN(C)c1ccc(cc1)Cl / C8H10ClN / 155.0502 / positive / -14.0157 / C-1H-2 / 0.36 / demethylation
Fipronil / Fipronil-sulfide / True pair / 120068-37-3 / 4.49 / Nc1c(c(nn1-c1c(Cl)cc(cc1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F / C12H4Cl2F6N4O1S1 / 435.9387 / 120067-83-6 / 5.62 / FC(F)(F)c2cc(Cl)c(n1nc(C#N)c(SC(F)(F)F)c1N)c(Cl)c2 / C12H4Cl2F6N4S1 / 419.9438 / positive / 15.9949 / O1 / 0.07 / sulphoxidation
Trimipramine / Trimipramine N-Oxide / True pair / 739-71-9 / 2.37 / CC(CN(C)C)CN1c2ccccc2CCc2ccccc12 / C20H26N2 / 294.2096 / 14171-70-1 / 3.63 / CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)C[N+](C)(C)[O-] / C20H26N2O / 310.2045 / positive / -15.9949 / O-1 / 0.23 / nitro reduction
Sulfamethoxazole / N4-Acetylsulfamethoxazole / True pair / 723-46-6 / 0.14 / Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1 / C10H11N3O3S1 / 253.0521 / 21312-10-7 / 0.10 / c1(ccc(cc1)NC(C)=O)S(Nc1cc(C)on1)(=O)=O / C12H13N3O4S / 295.0627 / positive / -42.0106 / C-2H-2O-1 / 0.27 / amide hydrolysis
Atrazine-desethyl / Propazine / True pair / 6190-65-4 / 1.54 / CC(C)Nc1nc(N)nc(Cl)n1 / C6H10ClN5 / 187.0625 / 139-40-2 / 2.61 / c1(nc(nc(n1)Cl)NC(C)C)NC(C)C / C9H16N5Cl / 229.1094 / positive / -42.0469 / C-3H-6 / 0.32 / desisopropyl
Flucytosine (5-FC) / 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine / True pair / 2022-85-7 / -1.06 / Nc1nc(=O)[nH]cc1F / C4H4FN3O / 129.0338 / 161599-46-8 / -0.67 / FC=1\C(=N/C(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](OC(=O)C)[C@H]2OC(=O)C)C)\N / C13H16FN3O6 / 329.1023 / positive / -200.0685 / C-9H-12O-5 / 0.85 / tertiary amine cleavage
Flucytosine (5-FC) / Emtricitabine / True pair / 2022-85-7 / -1.06 / Nc1nc(=O)[nH]cc1F / C4H4FN3O / 129.0338 / 143491-57-0 / -0.90 / FC=1\C(=N/C(=O)N(C=1)[C@H]2O[C@H](SC2)CO)\N / C8H10FN3O3S / 247.0427 / positive / -118.0089 / C-4H-6O-2S-1 / 0.73 / tertiary amine cleavage
Mianserin / Mianserin-N-Oxide / True pair / 24219-97-4 / 3.57 / CN1CCN2C(C1)c1ccccc1Cc1ccccc21 / C18H20N2 / 264.1626 / 62510-46-7 / 2.71 / C[N+]1(CCN2c3ccccc3Cc4ccccc4C2C1)[O-] / C18H20N2O / 280.1576 / positive / -15.995 / O-1 / 0.25 / nitro reduction
Simazine-2-hydroxy / Simeton / True pair / 03.11.2599 / 1.25 / CCNc1nc(O)nc(NCC)n1 / C7H13N5O / 183.112 / 673-04-1 / 1.39 / c1(nc(nc(n1)OC)NCC)NCC / C8H15N5O1 / 197.1277 / positive / -14.0157 / C-1H-2 / 0.18 / demethylation
Betamethasone / Betamethasone 21 / True pair / 378-44-9 / 1.68 / C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO / C22H29FO5 / 392.1999 / 987-24-6 / 2.12 / O=C(OCC(=O)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C)C / C24H31FO6 / 434.2105 / positive / -42.0106 / C-2H-2O-1 / 0.21 / ester cleavage
Thiamphenicol / Florfenicol / True pair / 3785-14-6 / -0.22 / CS(=O)(=O)c1ccc(cc1)C(O)C(CO)NC(=O)C(Cl)Cl / C12H15Cl2NO5S / 355.0048 / 73231-34-2 / 0.67 / CS(=O)(=O)C1=CC=C(C=C1)C(C(CF)NC(=O)C(Cl)Cl)O / C12H14Cl2FNO4S / 357.0005 / positive / -1.9957 / H1O1F-1 / 0.20 / dehalogenation
Perfluorodecyl phosphate / Bisperfluorodecyl phosphate / True pair / n.a. / 2.57 / OP(O)(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F / C10H6F17O4P / 543.9732 / 678-41-1 / 9.62 / FC(F)(CCOP(=O)(OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F / C20H9F34O4P / 989.9696 / positive / -445.9964 / C-10H-3F-17 / 0.67 / cleavage
Propazine-2-hydroxy / Prometryn / True pair / 7374-53-0 / 2.08 / CC(C)Nc1nc(O)nc(NC(C)C)n1 / C9H17N5O / 211.1433 / 7287-19-6 / 2.99 / c1(nc(NC(C)C)nc(n1)SC)NC(C)C / C10H19N5S / 241.1361 / positive / -29.9928 / C-1H-2O1S-1 / 0.17 / oxidation
Propazine-2-hydroxy / Propazine / True pair / 7374-53-0 / 2.08 / CC(C)Nc1nc(O)nc(NC(C)C)n1 / C9H17N5O / 211.1433 / 139-40-2 / 2.61 / c1(nc(nc(n1)Cl)NC(C)C)NC(C)C / C9H16N5Cl / 229.1094 / positive / -17.9661 / H1O1Cl-1 / 0.28 / dehalogenation
Amisulpride / Amisulpride N-Oxide / True pair / 71675-85-9 / -0.08 / CCN1CCCC1CNC(=O)c1cc(c(N)cc1OC)S(=O)(=O)CC / C17H27N3O4S / 369.1722 / 71676-01-2 / -0.87 / CC[N+]1(CCCC1CNC(=O)C2=CC(=C(C=C2OC)N)S(=O)(=O)CC)[O-] / C17H27N3O5S / 385.1671 / positive / -15.9949 / O-1 / 0.20 / nitro reduction
4-Aminoantipyrine / 4-Acetamidoantipyrine / True pair / 83-07-8 / 0.33 / Cc1c(N)c(=O)n(-c2ccccc2)n1C / C11H13N3O1 / 203.1059 / 83-15-8 / 0.15 / CC(=O)NC=2C(=O)N(c1ccccc1)N(C)C=2C / C13H15N3O2 / 245.1164 / positive / -42.0105 / C-2H-2O-1 / 0.31 / secondary amine cleavage
4-Aminoantipyrine / 4-Formylaminoantipyrine / True pair / 83-07-8 / 0.33 / Cc1c(N)c(=O)n(-c2ccccc2)n1C / C11H13N3O1 / 203.1059 / 1672-58-8 / 0.11 / O=C2C(\NC=O)=C(\C)N(C)N2c1ccccc1 / C12H13N3O2 / 231.1008 / positive / -27.9949 / C-1O-1 / 0.23 / secondary amine cleavage
4-Chlorophenol / Climbazol / True pair / 106-48-9 / 2.27 / Oc1ccc(Cl)cc1 / C6H5ClO / 128.0029 / 38083-17-9 / 4.25 / CC(C)(C)C(=O)C(N1C=CN=C1)OC2=CC=C(C=C2)Cl / C15H17ClN2O2 / 292.0979 / positive / -164.095 / C-9H-12O-1N-2 / 0.87 / ether cleavage
4-Chlorophenol / Difenoconazole / True pair / 106-48-9 / 2.27 / Oc1ccc(Cl)cc1 / C6H5ClO / 128.0029 / 119446-68-3 / 4.86 / Clc4ccc(Oc1ccc(c(Cl)c1)C2(OCC(O2)C)Cn3ncnc3)cc4 / C19H17Cl2N3O3 / 405.0647 / positive / -277.0618 / C-13H-12Cl-1O-2N-3 / 0.93 / ether cleavage
Irgarol-descyclopropyl / Terbutryn / True pair / 30125-65-6 / 2.19 / CSc1nc(N)nc(NC(C)(C)C)n1 / C8H15N5S / 213.1048 / 886-50-0 / 2.85 / c1(nc(nc(n1)SC)NCC)NC(C)(C)C / C10H19N5S1 / 241.1361 / positive / -28.0313 / C-2H-4 / 0.21 / deethylation
Atrazine-desethyl-2-hydroxy / Atrazine-desethyl / True pair / 19988-24-0 / 1.01 / CC(C)Nc1nc(N)nc(O)n1 / C6H11N5O / 169.0964 / 6190-65-4 / 1.54 / c1(nc(nc(n1)Cl)N)NC(C)C / C6H10ClN5 / 187.0625 / positive / -17.9661 / H1O1Cl-1 / 0.32 / dehalogenation
Atrazine-desethyl-2-hydroxy / Atrazine-2-hydroxy / True pair / 19988-24-0 / 1.01 / CC(C)Nc1nc(N)nc(O)n1 / C6H11N5O / 169.0964 / 2163-68-0 / 1.66 / c1(nc(nc(n1)O)NCC)NC(C)C / C8H15N5O / 197.1277 / positive / -28.0313 / C-2H-4 / 0.22 / secondary amine cleavage
Atrazine-desethyl-2-hydroxy / Propazine-2-hydroxy / True pair / 19988-24-0 / 1.01 / CC(C)Nc1nc(N)nc(O)n1 / C6H11N5O / 169.0964 / 7374-53-0 / 2.08 / n(c(nc1NC(C)C)O)c(n1)NC(C)C / C9H17N5O / 211.1433 / positive / -42.0469 / C-3H-6 / 0.31 / desisopropyl
Terbutylazine-2-hydroxy / Terbumeton / True pair / 66753-07-9 / 1.94 / CCNc1nc(O)nc(NC(C)(C)C)n1 / C9H17N5O / 211.1433 / 33693-04-8 / 2.09 / c1(nc(nc(n1)OC)NCC)NC(C)(C)C / C10H19N5O / 225.159 / positive / -14.0157 / C-1H-2 / 0.17 / demethylation
Terbutylazine-2-hydroxy / Terbutryn / True pair / 66753-07-9 / 1.94 / CCNc1nc(O)nc(NC(C)(C)C)n1 / C9H17N5O / 211.1433 / 886-50-0 / 2.85 / c1(nc(nc(n1)SC)NCC)NC(C)(C)C / C10H19N5S1 / 241.1361 / positive / -29.9928 / C-1H-2O1S-1 / 0.17 / oxidation
N-Bisdesmethyl Tramadol / N-Desmethyltramadol / True pair / 931115-27-4 / -0.88 / COc1cccc(c1)C1(O)CCCCC1CN / C14H21NO2 / 235.1572 / 80456-81-1 / -0.66 / CNCC1CCCCC1(c2cccc(c2)OC)O / C15H23NO2 / 249.1729 / positive / -14.0157 / C-1H-2 / 0.10 / demethylation
Sulfathiazole / N4-Acetylsulfathiazole / True pair / 72-14-0 / 0.69 / Nc1ccc(cc1)S(=O)(=O)Nc1nccs1 / C9H9N3O2S2 / 255.0136 / 127-76-4 / 0.69 / c1(ccc(NC(=O)C)cc1)S(=O)(NC2=NC=CS2)=O / C11H11N3O3S2 / 297.0242 / positive / -42.0106 / C-2H-2O-1 / 0.29 / amide hydrolysis
Lidocaine / Lidocaine-N-Oxide / True pair / 137-58-6 / 2.02 / CCN(CC)CC(=O)Nc1c(C)cccc1C / C14H22N2O / 234.1732 / 2903-45-9 / 1.72 / CC[N+](CC)(CC(=O)NC1=C(C=CC=C1C)C)[O-] / C14H22N2O2 / 250.1681 / positive / -15.9949 / O-1 / 0.28 / nitro reduction
Atrazine-desisopropyl / Simazine / True pair / 1007-28-9 / 1.12 / CCNc1nc(N)nc(Cl)n1 / C5H8ClN5 / 173.0468 / 122-34-9 / 1.78 / c1(nc(nc(n1)Cl)NCC)NCC / C7H12ClN5 / 201.0781 / positive / -28.0313 / C-2H-4 / 0.25 / deethylation
Atrazine-desisopropyl / Sebuthylazine / True pair / 1007-28-9 / 1.12 / CCNc1nc(N)nc(Cl)n1 / C5H8ClN5 / 173.0468 / 7286-69-3 / 2.72 / n1c(nc(Cl)nc1NCC)NC(CC)C / C9H16Cl1N5 / 229.1094 / positive / -56.0626 / C-4H-8 / 0.41 / cleavage
Pheniramine / Pheniramine-N-oxide / True pair / 86-21-5 / 0.53 / CN(C)CCC(c1ccccc1)c1ccccn1 / C16H20N2 / 240.1626 / 12656-98-3 / 1.85 / C[N+](C)(CCC(c1ccccc1)c2ccccn2)[O-] / C16H20N2O / 256.1576 / positive / -15.995 / O-1 / 0.25 / nitro reduction
Ticlopidine / Clopidogrel carboxylic acid / True pair / 55142-85-3 / 4.01 / Clc1ccccc1CN1CCc2sccc2C1 / C14H14ClNS / 263.0535 / 144457-28-3 / 1.23 / C1CN(CC2=C1SC=C2)C(C3=CC=CC=C3Cl)C(=O)O / C15H14ClNO2S / 307.0434 / positive / -43.9899 / C-1O-2 / 0.44 / decarboxylation
Pyrimidinol / Diazoxon / True pair / 2814-20-2 / 2.29 / CC(C)c1nc(C)cc(O)n1 / C8H12N2O1 / 152.095 / 962-58-3 / 3.38 / O(c1nc(nc(c1)C)C(C)C)P(OCC)(OCC)=O / C12H21N2O4P / 288.1239 / positive / -136.0289 / C-4H-9O-3P-1 / 0.62 / ester cleavage
2-Mercaptobenzothiazole / 2-(Methylsulfanyl)-1,3-benzothiazole / True pair / 149-30-4 / 2.77 / Sc1nc2ccccc2s1 / C7H5NS2 / 166.9863 / 615-22-5 / 3.43 / CSC1=NC2=CC=CC=C2S1 / C8H7NS2 / 181.002 / positive / -14.0157 / C-1H-2 / 0.26 / demethylation
Diuron-desdimethyl / Diuron-desmethyl / True pair / 08.02.2327 / 2.09 / NC(=O)Nc1ccc(Cl)c(Cl)c1 / C7H6Cl2N2O / 203.9857 / 3567-62-2 / 2.31 / c1(cc(c(Cl)cc1)Cl)NC(NC)=O / C8H8Cl2N2O / 218.0014 / positive / -14.0157 / C-1H-2 / 0.15 / urea derivative
Perfluorooctyl phosphate / Bisperfluorooctyl phosphate / True pair / n.a. / 1.17 / OP(O)(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F / C8H6F13O4P / 443.9796 / n.a. / 6.82 / FC(F)(CCOP(=O)(OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F / C16H9F26O4P / 789.9823 / positive / -346.0027 / C-8H-3F-13 / 0.65 / ester cleavage
4-Isopropylaniline / Isoproturon-didemethyl / True pair / 99-88-7 / 2.39 / CC(C)c1ccc(N)cc1 / C9H13N / 135.1048 / 56046-17-4 / 2.12 / N(C(=O)N)c1ccc(cc1)C(C)C / C10H14N2O / 178.1106 / positive / -43.0058 / C-1H-1N-1O-1 / 0.42 / urea derivative
4-Isopropylaniline / Isoproturon-monodemethyl / True pair / 99-88-7 / 2.39 / CC(C)c1ccc(N)cc1 / C9H13N / 135.1048 / 34123-57-4 / 2.35 / N(C(=O)Nc1ccc(cc1)C(C)C)C / C11H16N2O / 192.1263 / positive / -57.0215 / C-2H-3N-1O-1 / 0.51 / urea derivative
Terbutylazine-desethyl-2-hydroxy / Terbutylazine-2-hydroxy / True pair / 66753-06-8 / 1.29 / CC(C)(C)Nc1nc(N)nc(O)n1 / C7H13N5O / 183.112 / 66753-07-9 / 1.94 / CCNC1=NC(O)=NC(NC(C)(C)C)=N1 / C9H17N5O / 211.1433 / positive / -28.0313 / C-2H-4 / 0.21 / deethylation
Terbutylazine-desethyl-2-hydroxy / Terbutylazine-desethyl / True pair / 66753-06-8 / 1.29 / CC(C)(C)Nc1nc(N)nc(O)n1 / C7H13N5O / 183.112 / 30125-63-4 / 1.82 / Nc1nc(NC(C)(C)C)nc(Cl)n1 / C7H12Cl1N5 / 201.0781 / positive / -17.9661 / H1O1Cl-1 / 0.31 / dehalogenation
Fenthion-sulfone / Fenthion-sulfoxide / True pair / 3761-42-0 / 2.02 / COP(=S)(OC)Oc1ccc(c(C)c1)S(C)(=O)=O / C10H15O5PS2 / 310.0099 / 3761-41-9 / 1.91 / CC1=C(C=CC(=C1)OP(=S)(OC)OC)S(=O)C / C10H15O4PS2 / 294.0149 / positive / 15.995 / O1 / 0.12 / sulfur reduction
Isoproturon-didemethyl / Isoproturon-monodemethyl / True pair / 56046-17-4 / 2.12 / CC(C)c1ccc(NC(N)=O)cc1 / C10H14N2O / 178.1106 / 34123-57-4 / 2.35 / N(C(=O)Nc1ccc(cc1)C(C)C)C / C11H16N2O / 192.1263 / positive / -14.0157 / C-1H-2 / 0.14 / demethylation
1-[(4-Chlorophenyl)phenylmethyl]piperazine / Meclozine / True pair / 303-26-4 / 1.59 / Clc1ccc(cc1)C(N1CCNCC1)c1ccccc1 / C17H19ClN2 / 286.1237 / 569-65-3 / 5.46 / Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)Cc4cccc(c4)C / C25H27ClN2 / 390.1863 / positive / -104.0626 / C-8H-8 / 0.52 / tertiary amine cleavage
1-[(4-Chlorophenyl)phenylmethyl]piperazine / Chlorcyclizine / True pair / 303-26-4 / 1.59 / Clc1ccc(cc1)C(N1CCNCC1)c1ccccc1 / C17H19ClN2 / 286.1237 / 82-93-9 / 3.15 / CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl / C18H21ClN2 / 300.1393 / positive / -14.0156 / C-1H-2 / 0.17 / demethylation
N,O-Didesmethylvenlafaxine / O-desmethylvenlafaxine / True pair / 135308-74-6 / -0.43 / CNCC(c1ccc(O)cc1)C1(O)CCCCC1 / C15H23N1O2 / 249.1729 / 93413-62-8 / 0.69 / CN(C)CC(C1=CC=C(C=C1)O)C2(CCCCC2)O / C16H25N1O2 / 263.1885 / positive / -14.0156 / C-1H-2 / 0.17 / demethylation
N,O-Didesmethylvenlafaxine / N-Desmethylvenlafaxine / True pair / 135308-74-6 / -0.43 / CNCC(c1ccc(O)cc1)C1(O)CCCCC1 / C15H23N1O2 / 249.1729 / 149289-30-5 / -0.30 / CNCC(C1=CC=C(C=C1)OC)C2(CCCCC2)O / C16H25N1O2 / 263.1885 / positive / -14.0156 / C-1H-2 / 0.16 / demethylation
Atrazine-2-hydroxy / Atraton / True pair / 2163-68-0 / 1.66 / CCNc1nc(O)nc(NC(C)C)n1 / C8H15N5O / 197.1277 / 1610-17-9 / 1.81 / COc1nc(NCC)nc(NC(C)C)n1 / C9H17N5O / 211.1433 / positive / -14.0156 / C-1H-2 / 0.18 / demethylation
Atrazine-2-hydroxy / Ametryn / True pair / 2163-68-0 / 1.66 / CCNc1nc(O)nc(NC(C)C)n1 / C8H15N5O / 197.1277 / 834-12-8 / 2.57 / S(c1nc(nc(n1)NC(C)C)NCC)C / C9H17N5S / 227.1205 / positive / -29.9928 / C-1H-2O1S-1 / 0.18 / desulphuration
Tramadol / Tramadol N-Oxide / True pair / 27203-92-5 / 0.24 / COc1cccc(c1)[C@@]1(O)CCCC[C@@H]1CN(C)C / C16H25NO2 / 263.1885 / 147441-56-3 / 1.33 / [O-][N+](C)(C)C[C@H]2CCCC[C@]2(O)c1cc(OC)ccc1 / C16H25NO3 / 279.1834 / positive / -15.9949 / O-1 / 0.24 / nitro reduction
3,4-Methylenedioxyamphetamine (MDA) / 3,4-Methylenedioxy-N-methylamphetamine (MDMA) / True pair / 4764-17-4 / -1.29 / CC(N)Cc1ccc2OCOc2c1 / C10H13NO2 / 179.0946 / 42542-10-9 / -1.03 / CC(CC1=CC2=C(C=C1)OCO2)NC / C11H15NO2 / 193.1103 / positive / -14.0157 / C-1H-2 / 0.13 / demethylation
3,4-Methylenedioxyamphetamine (MDA) / 3,4-Methylenedioxy-N-ethylamphetamine (MDEA) / True pair / 4764-17-4 / -1.29 / CC(N)Cc1ccc2OCOc2c1 / C10H13NO2 / 179.0946 / 14089-52-2 / -0.71 / CCNC(C)CC1=CC2=C(C=C1)OCO2 / C12H17NO2 / 207.1259 / positive / -28.0313 / C-2H-4 / 0.24 / deethylation
Nortriptyline / Amitriptyline / True pair / 72-69-5 / 1.39 / CNCCC=C1c2ccccc2CCc2ccccc12 / C19H21N / 263.1674 / 50-48-6 / 2.12 / C1(\c2c(CCc3c1cccc3)cccc2)=C\CCN(C)C / C20H23N / 277.183 / positive / -14.0156 / C-1H-2 / 0.17 / demethylation
Sulfadiazine / N4-Acetylsulfadiazine / True pair / 68-35-9 / 0.13 / Nc1ccc(cc1)S(=O)(=O)Nc1ncccn1 / C10H10N4O2S / 250.0524 / 127-74-2 / 0.15 / c1nc(NS(c2ccc(cc2)NC(C)=O)(=O)=O)ncc1 / C12H12N4O3S / 292.063 / positive / -42.0106 / C-2H-2O-1 / 0.27 / amide hydrolysis
Morphine / Codeine / True pair / 57-27-2 / -0.98 / CN1CC[C@@]23[C@H]4Oc5c2c(C[C@@H]1[C@@H]3C=C[C@@H]4O)ccc5O / C17H19NO3 / 285.1365 / 76-57-3 / -0.83 / CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O / C18H21NO3 / 299.1521 / positive / -14.0156 / C-1H-2 / 0.15 / demethylation
Cortisone / Hydrocortisone / True pair / 53-06-5 / 1.66 / C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO / C21H28O5 / 360.1937 / 50-23-7 / 1.28 / O=C4\C=C2/[C@]([C@H]1[C@@H](O)C[C@@]3([C@@](O)(C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4 / C21H30O5 / 362.2093 / positive / -2.0156 / H-2 / 0.07 / dehydrogenation
4-Chlorobenzophenone / Cetirizine N-Oxide / True pair / 134-85-0 / 4.04 / Clc1ccc(cc1)C(=O)c1ccccc1 / C13H9ClO / 216.0342 / 1076199-80-8 / -0.69 / C1C[N+](CCN1C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl)(CCOCC(=O)O)[O-] / C21H25ClN2O4 / 404.1503 / positive / -188.1161 / C-8H-16O-3N-2 / 0.83 / cleavage
4-Chlorobenzophenone / 1-[(4-Chlorophenyl)phenylmethyl]piperazine / True pair / 134-85-0 / 4.04 / Clc1ccc(cc1)C(=O)c1ccccc1 / C13H9ClO / 216.0342 / 303-26-4 / 1.59 / C1CN(CCN1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl / C17H19ClN2 / 286.1237 / positive / -70.0895 / C-4H-10O1N-2 / 0.59 / cleavage
4-Chlorobenzophenone / Cetirizine / True pair / 134-85-0 / 4.04 / Clc1ccc(cc1)C(=O)c1ccccc1 / C13H9ClO / 216.0342 / 83881-51-0 / 0.81 / C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl / C21H25ClN2O3 / 388.1554 / positive / -172.1212 / C-8H-16O-2N-2 / 0.79 / cleavage
4-Chlorobenzophenone / Meclozine / True pair / 134-85-0 / 4.04 / Clc1ccc(cc1)C(=O)c1ccccc1 / C13H9ClO / 216.0342 / 569-65-3 / 5.46 / Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)Cc4cccc(c4)C / C25H27ClN2 / 390.1863 / positive / -174.1521 / C-12H-18O1N-2 / 0.77 / cleavage
4-Chlorobenzophenone / Chlorcyclizine / True pair / 134-85-0 / 4.04 / Clc1ccc(cc1)C(=O)c1ccccc1 / C13H9ClO / 216.0342 / 82-93-9 / 3.15 / CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl / C18H21ClN2 / 300.1393 / positive / -84.1051 / C-5H-12O1N-2 / 0.59 / cleavage
Chloridazone-desphenyl / Chloridazone-methyl-desphenyl / True pair / 6339-19-1 / -0.78 / Nc1cn[nH]c(=O)c1Cl / C4H4ClN3O / 145.0043 / 17254-80-7 / -0.55 / ClC(=C(C=N1)N)C(=O)N1C / C5H6ClN3O / 159.0199 / positive / -14.0156 / C-1H-2 / 0.30 / demethylation
Sulfamethazine / N4-Acetylsulfamethazine / True pair / 57-68-1 / 0.39 / Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1 / C12H14N4O2S / 278.0837 / 100-90-3 / 0.41 / O=S(=O)(c1ccc(cc1)NC(=O)C)Nc1nc(cc(n1)C)C / C14H16N4O3S / 320.0943 / positive / -42.0106 / C-2H-2O-1 / 0.25 / amide hydrolysis
1H-Benzotriazole / 1H-Benzotriazole-5-carboxylic acid / True pair / 95-14-7 / 1.29 / c1ccc2[nH]nnc2c1 / C6H5N3 / 119.0483 / 23814-12-2 / -2.20 / c1cc2c(cc1C(=O)O)nn[nH]2 / C7H5N3O2 / 163.0382 / positive / -43.9899 / C-1O-2 / 0.57 / decarboxylation
Venlafaxine / Venlafaxine N-Oxide / True pair / 93413-69-5 / 0.84 / COc1ccc(cc1)C(CN(C)C)C1(O)CCCCC1 / C17H27NO2 / 277.2042 / 1094598-37-4 / 1.61 / OC1(C(C2=CC=C(OC)C=C2)C[N+](C)(C)[O-])CCCCC1 / C17H27NO3 / 293.1991 / positive / -15.9949 / O-1 / 0.23 / nitro reduction