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

General Information of Drug (ID: DR0022)
Drug Name
O-Benzylguanine
Synonyms
O(6)-Benzylguanine; 6-O-benzylguanine; O(6)-Bgua; Purine, 2-amino-6-(benzyloxy)-; o6-benzylguanine; 01KC87F8FE; 19916-73-5; 1H-Purin-2-amine, 6-(phenylmethoxy)-; 2-Amino-6-(benzyloxy)purine; 2-Amino-6-(phenylmethoxy)-9H-purine; 2-amino-6-benzyloxypurine; 6-(Benzyloxy)-7H-purin-2-amine; 6-(Benzyloxy)guanine; 6-(Phenylmethoxy)-1H-purin-2-amine; 6-(benzyloxy)-9H-purin-2-amine; 6-BENZYLGUANINE; 6-Benzyloxy guanine; 6-Benzyloxyguanine; 6-O-Benzylguanine; 6-benzyloxy-7H-purin-2-amine; CHEMBL407874; MFCD00269931; NSC 637037; O6-BG; UNII-01KC87F8FE
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 241.25 Topological Polar Surface Area 89.7
Heavy Atom Count 18 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4578
CAS Number
19916-73-5
TTD Drug ID
D0B5BG
Formula
C12H11N5O
Canonical SMILES
C1=CC=C(C=C1)COC2=NC(=NC3=C2NC=N3)N
InChI
1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
InChIKey
KRWMERLEINMZFT-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
6-O-benzyl-8-oxoguanine DM004053 N. A. Oxidation - Oxidationn 1 [2]
8-oxoguanine DM004054
135625294
Oxidation - Debenzylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004428 O-Benzylguanine 6-O-benzyl-8-oxoguanine Oxidation - Oxidationn CYP1A1 ... [2]
MR004429 6-O-benzyl-8-oxoguanine 8-oxoguanine Oxidation - Debenzylation CYP1A1 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Inhibition of human O6-alkylguanine-DNA alkyltransferase and potentiation of the cytotoxicity of chloroethylnitrosourea by 4(6)-(benzyloxy)-2,6(4)-diamino-5-(nitro or nitroso)pyrimidine derivatives and analogues. J Med Chem. 1998 Feb 12;41(4):503-8.
2 Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: implications for dacarbazine activation. Clin Cancer Res. 2001 Dec;7(12):4239-44.
3 Human liver oxidative metabolism of O6-benzylguanine. Biochem Pharmacol. 1995 Oct 26;50(9):1385-9.

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