Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1985)
Drug Name
N-nonylphenol
Synonyms
Nonylphenol (mixed); Phenol, 4-nonyl-; Phenol, nonyl derivs.; Phenol, p-nonyl-; p -n -Nonylphenol; p-Nonylphenol; p-n-Nonylphenol; p-nonyl phenol; 4-N-nonylphenol; para Nonyl phenol; para-Nonylphenol; 1-(4-Hydroxyphenyl)nonane; 104-40-5; 4-NP; 4-Nonyl Phenol-13C6; 4-Nonyl-Phenol; 4-n-Nonyl phenol; 4-n-Nonylphenol; 4-nonyl phenol; 4-nonylphenol; 68081-86-7; BRN 2047450; CCRIS 1251; CHEBI:34440; DSSTox_CID_1857; IGFHQQFPSIBGKE-UHFFFAOYSA-N; DSSTox_GSID_33836; DSSTox_RID_79098; EINECS 203-199-4; HSDB 5359; MFCD00002396; P-NONYLPHENOL (ENDOCRINE DISRUPTER)
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 220.35 Topological Polar Surface Area 20.2
Heavy Atom Count 16 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
1752
ChEBI ID
CHEBI:34440
CAS Number
104-40-5
Formula
C15H24O
Canonical SMILES
CCCCCCCCCC1=CC=C(C=C1)O
InChI
1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3
InChIKey
IGFHQQFPSIBGKE-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-(1,5-Dihydroxynonyl)phenol DM004044 N. A. Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(1,6-Dihydroxynonyl)phenol DM004043 N. A. Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(1,7-Dihydroxynonyl)phenol DM004042 N. A. Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(1,8-Dihydroxynonyl)phenol DM004041 N. A. Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(1-Hydroxynonyl)phenol DM004028
162318955
Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(6-Hydroxynonyl)phenol DM004045 N. A. Oxidation - Alkyl-chain hydroxylation 1 [3]
4-(7-Hydroxynonyl)phenol DM004039 N. A. Oxidation - Hydrolyzationn 1 [3]
4-(8-Hydroxynonyl)phenol DM004037
101099647
Oxidation - Hydrolyzationn 1 [3]
9-(4-Hydroxyphenyl)nonanoic acid DM004013
10422225
Unclear 1 [3]
(4-Hydroxyphenyl)octanoic acid DM004014 N. A. Unclear 2 [3]
7-(4-Hydroxyphenyl)nonanal DM004040 N. A. Oxidation - Hydrolyzationn 2 [3]
8-(4-Hydroxyphenyl)nonanal DM004038 N. A. Oxidation - Hydrolyzationn 2 [3]
9-Hydroxy-9-(4-hydroxyphenyl) nonanoic acid DM004029
102138757
Oxidation - Alkyl-chain hydroxylation 2 [3]
7-(4-Hydroxyphenyl)heptanoic acid DM004015
14822017
Unclear 3 [3]
7-Hydroxy-7-(4-hydroxyphenyl)heptanoic acid DM004030 N. A. Oxidation - Alkyl-chain hydroxylation 3 [3]
6-(4-Hydroxyphenyl)hexanoic acid DM004016
247362
Unclear 4 [3]
6-Hydroxy-6-(4-hydroxyphenyl)hexanoic acid DM004031 N. A. Oxidation - Alkyl-chain hydroxylation 4 [3]
5-(4-Hydroxyphenyl)pentanoic acid DM004017
7016423
Unclear 5 [3]
5-Hydroxy-5-(4-hydroxyphenyl) pentanoic acid DM004032
166885670
Oxidation - Alkyl-chain hydroxylation 5 [3]
6-(3,4-Dihydroxyphenyl)hexanoic acid DM004036
13519335
Oxidation - Hydrolyzationn 5 [3]
4-(4-Hydroxyphenyl)butanoic acid DM004018
279983
Unclear 6 [3]
4-Hydroxy-4-(4-hydroxyphenyl) butanoic acid DM004033
56632628
Oxidation - Alkyl-chain hydroxylation 6 [3]
5-(3,4-Dihydroxyphenyl)pentanoic acid DM004035
49831816
Oxidation - Hydrolyzationn 6 [3]
3-(4-Hydroxyphenyl) propionic acid DM003390
10394
Unclear 7 [3]
4-(3,4-Dihydroxyphenyl)butanoic acid DM004034
54526520
Oxidation - Hydrolyzationn 7 [3]
4-Hydroxybenzoic acid DM004023
135
Oxidation - Alkyl-chain hydroxylation 7 [3]
3-(3',4'-dihydroxyphenyl)propionic acid DM002604
348154
Oxidation - Hydrolyzationn 8 [3]
p-Coumaric acid DM003945
637542
Unclear 8 [3]
Protocatechuate DM002607
72
Oxidation - Alkyl-chain hydroxylation 8 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Unclear 9 [3]
Caffeic acid DM003530
689043
Oxidation - Hydrolyzationn 9 [3]
(3,4-Dihydroxyphenyl)acetic acid DM000280
547
Oxidation - Hydrolyzationn 10 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Unclear 10 [3]
1-(4-hydroxyphenyl)ethanone DM004022
7469
Unclear 10 [3]
4-Hydroxybenzoic acid DM004023
135
Unclear 11 [3]
Protocatechuate DM002607
72
Oxidation - Hydrolyzationn 11 [3]
Protocatechuate DM002607
72
Unclear 12 [3]
⏷ Show the Full List of 37  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004390 N-nonylphenol 9-(4-Hydroxyphenyl)nonanoic acid Unclear Unclear [3]
MR004407 N-nonylphenol 4-(1-Hydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004417 N-nonylphenol 4-(8-Hydroxynonyl)phenol Oxidation - Hydrolyzationn Unclear [3]
MR004419 N-nonylphenol 4-(7-Hydroxynonyl)phenol Oxidation - Hydrolyzationn Unclear [3]
MR004421 N-nonylphenol 4-(1,8-Dihydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004422 N-nonylphenol 4-(1,7-Dihydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004423 N-nonylphenol 4-(1,6-Dihydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004424 N-nonylphenol 4-(1,5-Dihydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004425 N-nonylphenol 4-(6-Hydroxynonyl)phenol Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004408 4-(1-Hydroxynonyl)phenol 9-Hydroxy-9-(4-hydroxyphenyl) nonanoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004420 4-(7-Hydroxynonyl)phenol 7-(4-Hydroxyphenyl)nonanal Oxidation - Hydrolyzationn Unclear [3]
MR004418 4-(8-Hydroxynonyl)phenol 8-(4-Hydroxyphenyl)nonanal Oxidation - Hydrolyzationn Unclear [3]
MR004391 9-(4-Hydroxyphenyl)nonanoic acid (4-Hydroxyphenyl)octanoic acid Unclear Unclear [3]
MR004392 (4-Hydroxyphenyl)octanoic acid 7-(4-Hydroxyphenyl)heptanoic acid Unclear Unclear [3]
MR004409 9-Hydroxy-9-(4-hydroxyphenyl) nonanoic acid 7-Hydroxy-7-(4-hydroxyphenyl)heptanoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004393 7-(4-Hydroxyphenyl)heptanoic acid 6-(4-Hydroxyphenyl)hexanoic acid Unclear Unclear [3]
MR004410 7-Hydroxy-7-(4-hydroxyphenyl)heptanoic acid 6-Hydroxy-6-(4-hydroxyphenyl)hexanoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004394 6-(4-Hydroxyphenyl)hexanoic acid 5-(4-Hydroxyphenyl)pentanoic acid Unclear Unclear [3]
MR004416 6-(4-Hydroxyphenyl)hexanoic acid 6-(3,4-Dihydroxyphenyl)hexanoic acid Oxidation - Hydrolyzationn Unclear [3]
MR004411 6-Hydroxy-6-(4-hydroxyphenyl)hexanoic acid 5-Hydroxy-5-(4-hydroxyphenyl) pentanoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004395 5-(4-Hydroxyphenyl)pentanoic acid 4-(4-Hydroxyphenyl)butanoic acid Unclear Unclear [3]
MR004415 5-(4-Hydroxyphenyl)pentanoic acid 5-(3,4-Dihydroxyphenyl)pentanoic acid Oxidation - Hydrolyzationn Unclear [3]
MR004412 5-Hydroxy-5-(4-hydroxyphenyl) pentanoic acid 4-Hydroxy-4-(4-hydroxyphenyl) butanoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004396 4-(4-Hydroxyphenyl)butanoic acid 3-(4-Hydroxyphenyl)propanoic acid Unclear Unclear [3]
MR004414 4-(4-Hydroxyphenyl)butanoic acid 4-(3,4-Dihydroxyphenyl)butanoic acid Oxidation - Hydrolyzationn Unclear [3]
MR004413 4-Hydroxy-4-(4-hydroxyphenyl) butanoic acid 4-Hydroxybenzoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004397 3-(4-Hydroxyphenyl)propanoic acid (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid Unclear Unclear [3]
MR004406 3-(4-Hydroxyphenyl)propanoic acid 3-(3,4-Dihydroxyphenyl)propanoic acid Oxidation - Hydrolyzationn Unclear [3]
MR014114 4-Hydroxybenzoic acid 3,4-Dihydroxybenzoic acid Oxidation - Alkyl-chain hydroxylation Unclear [3]
MR004398 (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid 2-(4-Hydroxyphenyl)acetic acid Unclear Unclear [3]
MR004405 (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid (2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid Oxidation - Hydrolyzationn Unclear [3]
MR004399 2-(4-Hydroxyphenyl)acetic acid 1-(4-hydroxyphenyl)ethanone Unclear Unclear [3]
MR004403 2-(4-Hydroxyphenyl)acetic acid (3,4-Dihydroxyphenyl)acetic acid Oxidation - Hydrolyzationn Unclear [3]
MR004404 2-(4-Hydroxyphenyl)acetic acid 2-(4-Hydroxyphenyl)acetic acid Unclear Unclear [3]
MR004400 1-(4-hydroxyphenyl)ethanone 4-Hydroxybenzoic acid Unclear Unclear [3]
MR004402 1-(4-hydroxyphenyl)ethanone 3,4-Dihydroxybenzoic acid Oxidation - Hydrolyzationn Unclear [3]
MR014115 4-Hydroxybenzoic acid 3,4-Dihydroxybenzoic acid Unclear Unclear [3]
⏷ Show the Full List of 37 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sulfotransferase 2A1 (SULT2A1) DME0074 Km = 0.0715 microM
ST2A1_HUMAN
[2]
References
1 Nonylphenol acts on prostate adenocarcinoma cells via estrogen molecular pathways. Ecotoxicol Environ Saf. 2019 Sep 30;180:412-419.
2 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
3 4-n-nonylphenol degradation by the genus Metarhizium with cytochrome P450 involvement

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.