Phase I - Functionalization of compounds

Strolin Benedetti M, Whomsley R, Baltes E. Involvement of enzymes other than CYPs in the oxidative metabolism of xenobiotics. Expert Opinion on Drug Metabolism & Toxicology. 2006 Nov 24;2(6):895–921. doi: 10.1517/17425255.2.6.895.; Guengerich FP. Cytochrome P450s and other enzymes in drug metabolism and toxicity. The AAPS Journal. 2006 Mar 01;8(1):e101–11. doi: 10.1208/aapsj080112.; Danielson PB. The cytochrome P450 superfamily: biochemistry, evolution and drug metabolism in humans. Curr Drug Metab. 2002 Dec;3(6):561–97. doi: 10.2174/1389200023337054. PMID: 12369887.

Metabolites

1,7-Dimethylxanthine

Formula: C7H8N4O2 (180.0647228)

CAS ID: 611-59-6

11-Deoxycortisol

Formula: C21H30O4 (346.214398)

CAS ID: 152-58-9

12-Hydroxydodecanoic acid

Formula: C12H24O3 (216.1725354)

CAS ID: 505-95-3

18-Hydroxycorticosterone

Formula: C21H30O5 (362.209313)

CAS ID: 561-65-9

3-Acetamidopropanal

Formula: C5H9NO2 (115.0633254)

CAS ID: 73323-68-9

4-Aminobiphenyl

Formula: C12H11N (169.0891446)

CAS ID: 92-67-1

4-Hydroxy-17beta-estradiol

Formula: C18H24O3 (288.1725354)

CAS ID: 5976-61-4

4-Hydroxycyclophosphamide

Formula: C7H15Cl2N2O3P (276.019731)

CAS ID: 40277-05-2

4-Hydroxyphenylacetaldehyde

Formula: C8H8O2 (136.0524268)

CAS ID: 7339-87-9

4-Methylpentanal

Formula: C6H12O (100.0888102)

CAS ID: 1119-16-0

5-Hydroxyindoleacetaldehyde

Formula: C10H9NO2 (175.0633254)

CAS ID: 1892-21-3

6beta-Hydroxytestosterone

Formula: C19H28O3 (304.2038338)

CAS ID: 62-99-7

9-cis-Retinoic acid

Formula: C20H28O2 (300.2089188)

CAS ID: 5300-03-8

Acetaldehyde

Formula: C2H4O (44.0262134)

CAS ID: 75-07-0

Acetaminophen

Formula: C8H9NO2 (151.0633254)

CAS ID: 103-90-2

Acetate

Formula: C2H4O2 (60.0211284)

CAS ID: 64-19-7

Aflatoxin B1

Formula: C17H12O6 (312.06338519999997)

CAS ID: 1162-65-8

Aldosterone

Formula: C21H28O5 (360.1936638)

CAS ID: 52-39-1

Ammonia

Formula: NH3 (17.0265478)

CAS ID: 7664-41-7

Androstenedione

Formula: C19H26O2 (286.1932696)

CAS ID: 63-05-8

Aromatic aldehyde

Formula: C7H6O (106.0418626)

CAS ID: 100-52-7

Benzene

Formula: C6H6 (78.0469476)

CAS ID: 71-43-2

Benzo[a]pyrene-4,5-oxide

Formula: C20H12O (268.0888102)

CAS ID: 37574-47-3

Caffeine

Formula: C8H10N4O2 (194.080372)

CAS ID: 58-08-2

Calcidiol

Formula: C27H44O2 (400.3341124)

CAS ID: 19356-17-3

Calcitriol

Formula: C27H44O3 (416.3290274)

CAS ID: 32222-06-3

Calcium cation

Formula: Ca (39.962591)

CAS ID: 14127-61-8

Carbon tetrachloride

Formula: CCl4 (151.875412)

CAS ID: 56-23-5

Carboxyphosphamide

Formula: C7H15Cl2N2O4P (292.014646)

CAS ID: 22788-18-7

Cerebrosterol

Formula: C27H46O2 (402.34976159999997)

CAS ID: 474-73-7

Chloroethylene oxide

Formula: C2H3ClO (77.9872418)

CAS ID: 7763-77-1

Cholesterol

Formula: C27H46O (386.3548466)

CAS ID: 57-88-5

Cl-

Formula: Cl (34.968853)

CAS ID: 16887-00-6

Cocaine

Formula: C17H21NO4 (303.1470506)

CAS ID: 50-36-2

Corticosterone

Formula: C21H30O4 (346.214398)

CAS ID: 50-22-6

Cortisol

Formula: C21H30O5 (362.209313)

CAS ID: 50-23-7

Coumarin

Formula: C9H6O2 (146.0367776)

CAS ID: 91-64-5

Cyclophosphamide

Formula: C7H15Cl2N2O2P. H2O (278.0353802)

CAS ID: 6055-19-2

Debrisoquin

Formula: C10H13N3 (175.1109418)

CAS ID: 1131-64-2

Estradiol-17beta

Formula: C18H24O2 (272.17762039999997)

CAS ID: 50-28-2

Estrone

Formula: C18H22O2 (270.1619712)

CAS ID: 53-16-7

Ethanol

Formula: C2H6O (46.0418626)

CAS ID: 64-17-5

Ethylene

Formula: C2H4 (28.0312984)

CAS ID: 74-85-1

Ethylene oxide

Formula: C2H4O (44.0262134)

CAS ID: 75-21-8

Formaldehyde

Formula: CH2O (30.0105642)

CAS ID: 50-00-0

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Halothane

Formula: C2HBrClF3 (195.89022319999998)

CAS ID: 151-67-7

Hydrogen

Formula: H2 (2.0156492)

CAS ID: 1333-74-0

Hydrogen peroxide

Formula: H2O2 (34.0054792)

CAS ID: 7722-84-1

Hydroquinone

Formula: C6H6O2 (110.0367776)

CAS ID: 123-31-9

Indole

Formula: C8H7N (117.0578462)

CAS ID: 120-72-9

Indolin-2-one

Formula: C8H7NO (133.0527612)

CAS ID: 59-48-3

Lanosterol

Formula: C30H50O (426.386145)

CAS ID: 79-63-0

Loperamide

Formula: C29H33ClN2O2 (476.22304280000003)

CAS ID: 53179-11-6

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Melatonin

Formula: C13H16N2O2 (232.1211716)

CAS ID: 73-31-4

Methanol

Formula: CH4O (32.0262134)

CAS ID: 67-56-1

N-Hydroxy-4-aminobiphenyl

Formula: C12H11NO (185.0840596)

CAS ID: 1204-79-1

NADP+

Formula: C21H29N7O17P3 (744.0832754)

CAS ID: 53-59-8

NADPH

Formula: C21H30N7O17P3 (745.0911)

CAS ID: 2646-71-1

Nicotinamide-beta-riboside

Formula: C11H15N2O5 (255.098092)

CAS ID: 1341-23-7

Olmesartan

Formula: C24H26N6O3 (446.20662860000004)

CAS ID: 144689-24-7

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Phenacetin

Formula: C10H13NO2 (179.09462380000002)

CAS ID: 62-44-2

Phenethylamine

Formula: C8H11N (121.0891446)

CAS ID: 64-04-0

Phenol

Formula: C6H6O (94.0418626)

CAS ID: 108-95-2

Phenylacetaldehyde

Formula: C8H8O (120.0575118)

CAS ID: 122-78-1

Phenytoin

Formula: C15H12N2O2 (252.0898732)

CAS ID: 57-41-0

Pregnenolone

Formula: C21H32O2 (316.24021719999996)

CAS ID: 145-13-1

Progesterone

Formula: C21H30O2 (314.224568)

CAS ID: 57-83-0

Resveratrol

Formula: C14H12O3 (228.0786402)

CAS ID: 501-36-0

Retinoate

Formula: C20H28O2 (300.2089188)

CAS ID: 302-79-4

S-Formylglutathione

Formula: C11H17N3O7S (335.0787172)

CAS ID: 50409-81-9

Skatole

Formula: C9H9N (131.0734954)

CAS ID: 83-34-1

Tamoxifen

Formula: C26H29NO (371.2249024)

CAS ID: 10540-29-1

Tamoxifen N-oxide

Formula: C26H29NO2 (387.2198174)

CAS ID: 75504-34-6

Testosterone

Formula: C19H28O2 (288.2089188)

CAS ID: 58-22-0

Thiamazole

Formula: C4H6N2S (114.02516759999999)

CAS ID: 60-56-0

Trimethylamine

Formula: C3H9N (59.0734954)

CAS ID: 75-50-3

Trimethylamine N-oxide

Formula: C3H9NO (75.0684104)

CAS ID: 1184-78-7

Tyramine

Formula: C8H11NO (137.0840596)

CAS ID: 51-67-2

Umbelliferone

Formula: C9H6O3 (162.03169259999999)

CAS ID: 93-35-6

Vinyl chloride

Formula: C2H3Cl (61.9923268)

CAS ID: 75-01-4

Vitamin D3

Formula: C27H44O (384.3391974)

CAS ID: 67-97-0

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

4-Hydroxydebrisoquine

Formula: C10H13N3O (191.1058568)

CAS ID: 59333-79-8

3-Methylene-indolenine

Formula: C9H7N (129.0578462)

CAS ID: 40642-83-9

Doxorubicinol

Formula: C27H31NO11 (545.1897016)

CAS ID: 54193-28-1

4-Hydroxyphenytoin

Formula: C15H12N2O3 (268.0847882)

CAS ID: 2784-27-2

Dextrorphan

Formula: C17H23NO (257.1779548)

CAS ID: 125-73-5

NAPQI

Formula: C8H7NO2 (149.0476762)

CAS ID: 50700-49-7

3-amino-propanal

Formula: C3H8NO (74.0605858)

CAS ID:

L-argininium(1+)

Formula: C6H15N4O2 (175.119495)

CAS ID: 17806-42-7

p-Phenetidine

Formula: C8H11NO (137.0840596)

CAS ID: 156-43-4

N-desmethyl loperamide

Formula: C28H31ClN2O2 (462.2073936)

CAS ID: 66164-07-6

Olmesartan medoxomil

Formula: C29H30N6O6 (558.222672)

CAS ID: 144689-63-4

formate

Formula: CHO2 (44.997654600000004)

CAS ID: 71-47-6

acetate

Formula: C2H3O2 (59.0133038)

CAS ID: 71-50-1

dodecanoate

Formula: C12H23O2 (199.1697958)

CAS ID: 115-05-9

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8

trifluoroacetyl chloride

Formula: C2ClF3O (131.9589776)

CAS ID: 354-32-5



Enzyme

EC Number name full name note
1.14.13.148 trimethylamine monooxygenase N,N,N-trimethylamine,NADPH:oxygen oxidoreductase (N-oxide-forming)
1.14.13.8 flavin-containing monooxygenase N,N-dimethylaniline,NADPH:oxygen oxidoreductase (N-oxide-forming)
1.14.14.154 sterol 14alpha-demethylase sterol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (14-methyl cleaving)
1.14.14.16 steroid 21-monooxygenase steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (21-hydroxylating)
1.14.15.6 cholesterol monooxygenase (side-chain-cleaving) cholesterol,reduced-adrenal-ferredoxin:oxygen oxidoreductase (side-chain-cleaving)
1.2.1.3 aldehyde dehydrogenase (NAD+) aldehyde:NAD+ oxidoreductase


Proteins

Protein ID name full name