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

General Information of Drug (ID: DR2710)
Drug Name
PhIP
Synonyms
(3H)PhIP; 1-Methyl-6-phenyl-1H-imidazo(4,5-b)pyridin-2-amine; 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine; 105650-23-5; 1H-Imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl- (9CI); 2-AMINO-1-METHYL-6-PHENYL-IMIDAZO [4,5-b] PYRIDINE; 2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine; 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine; 909C6UN66T; AC1L1BO3; AC1Q4WMI; ACMC-1BRGI; BRN 5951264; CCRIS 2954; CHEBI:76290; CHEMBL1213271; CTK0I0185; DTXSID3037628; HSDB 7768; PIQ; PhIP; SCHEMBL151718; UNII-909C6UN66T
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 224.26 Topological Polar Surface Area 56.7
Heavy Atom Count 17 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
1530
PubChem SID
3157795 ; 5575539 ; 7889895 ; 8151167 ; 14773663 ; 24439858 ; 26706921 ; 47205348 ; 47213254 ; 49655368 ; 49981200 ; 50077334 ; 53790715 ; 56311095 ; 57320930 ; 69519515 ; 75586395 ; 84933929 ; 85083684 ; 88802108 ; 99444869 ; 103101540 ; 104239441 ; 104297984 ; 117521388 ; 125362482 ; 129407608 ; 135020564 ; 137009621 ; 144233754 ; 160969439 ; 162127724 ; 162271907 ; 162476045 ; 164223590 ; 164796165 ; 164835618 ; 170474404 ; 174558552 ; 184564905 ; 198966617 ; 202556526 ; 204414277 ; 215774860 ; 223515797 ; 223541200 ; 226516667 ; 249790662 ; 252330901
ChEBI ID
CHEBI:76290
CAS Number
105650-23-5
TTD Drug ID
D00ZAJ
Formula
C13H12N4
Canonical SMILES
CN1C2=C(N=CC(=C2)C3=CC=CC=C3)N=C1N
InChI
1S/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16)
InChIKey
UQVKZNNCIHJZLS-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'-hydroxy-PhIP DM015932
15897928
Unclear - Unclear 1 [3]
4'-hydroxy-PhIP DM015932
15897928
Oxidation - Hydroxylation 1 [3]
PhIP N2-glucuronide metabolite DM019906 N. A. Conjugation - Glucuronidation 1 [3]
4'-Hydroxy-PhIP-O-Sulfate metabolite DM015162
129761
Conjugation - Sulfation 2 [3]
N2-acetoxy-PhIP DM016043
25092289
Conjugation - Acetylation 2 [3]
N2-hydroxy-PhIP-N2-glucuronide metabolite DM016464
101621064
Conjugation - Glucuronidation 2 [3]
N2-hydroxy-PhIP-N3-glucuronide metabolite DM016760
154699553
Conjugation - Glucuronidation 2 [3]
N2-sulfonyloxy-PhIP DM016315
71448983
Conjugation - Sulfation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012698 PhIP 4'-hydroxy-PhIP Oxidation - Hydroxylation Unclear [3]
MR012704 PhIP PhIP N2-glucuronide metabolite Conjugation - Glucuronidation Unclear [3]
MR012699 4'-hydroxy-PhIP 4'-Hydroxy-PhIP-O-Sulfate metabolite Conjugation - Sulfation Unclear [3]
MR012700 N2-hydroxy-PhIP N2-acetoxy-PhIP Conjugation - Acetylation Unclear [3]
MR012701 N2-hydroxy-PhIP N2-sulfonyloxy-PhIP Conjugation - Sulfation Unclear [3]
MR012702 N2-hydroxy-PhIP N2-hydroxy-PhIP-N2-glucuronide metabolite Conjugation - Glucuronidation Unclear [3]
MR012703 N2-hydroxy-PhIP N2-hydroxy-PhIP-N3-glucuronide metabolite Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Glycerol/diol dehydratase (dhaB) DME1816 Blautia obeum
A0A174P2C4_9FIRM
4.2.1.30
[2]
Glycerol/diol dehydratase (dhaB) DME1869 Flavonifractor plautii
A0A174IA87_FLAPL
4.2.1.30
[2]
Glycerol/diol dehydratase (dhaB) DME1904 Anaerobutyricum hallii
A0A174DDZ6_9FIRM
4.2.1.30
[2]
Glycerol/diol dehydratase (dhaB) DME1923 Lactobacillus reuteri
H6V877_LACRE
4.2.1.30
[2]
References
1 PubChem 2019 update: improved access to chemical data. Nucleic Acids Res. 2019 Jan 8; 47(D1):D1102-1109. (PubChem CID: 1530)
2 Gut microbial beta-glucuronidase and glycerol/diol dehydratase activity contribute to dietary heterocyclic amine biotransformation. BMC Microbiol. 2019 May 16;19(1):99.
3 Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2

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