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

General Information of Drug (ID: DR1974)
Drug Name
A-estradiol
Synonyms
Estra-1,3,5(10)-triene-2,3,17beta-triol; MLS000069506; NSC 61711; 2-Hydroxyestradiol; AYU2L67YUU; DILDHNKDVHLEQB-XSSYPUMDSA-N; (17beta)-Estra-1,3,5(10)-triene-2,3,17-triol; 1,3,5(10)-estratriene-2,3,17Beta-triol; 2,3,17beta-Trihydroxy-1,3,5(10)-Estratriene; 2-Hydroxy-17; 2-Hydroxyestradiol-17beta; 2-OH-E2; 2-OH-Estradiol; 2-hydroxy-17beta-estradiol; 2-hydroxy-estradiol; 2bw7; 362-05-0; BRN 2219367; CCRIS 8709; CHEBI:28744; CHEMBL467987; ECS; ESTRA-1,3,5(10)-TRIENE-2,3,17-beta-TRIOL; SMR000058615; UNII-AYU2L67YUU
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 288.4 Topological Polar Surface Area 60.7
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
247304
ChEBI ID
CHEBI:28744
CAS Number
362-05-0
TTD Drug ID
D00PZE
Formula
C18H24O3
Canonical SMILES
CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O
InChI
1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
InChIKey
DILDHNKDVHLEQB-XSSYPUMDSA-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
2-methoxyestradiol (2MEOE) DM001720
66414
Conjugation - Methylation 1 [2]
Estradiol-2,3-semiquinone DM001718 N. A. Unclear 1 [5]
Estradiol-2,3-quinone DM001719
66393
Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000098 A-estradiol Estradiol-2,3-semiquinone Unclear msp1 [5]
MR000099 A-estradiol 2-methoxyestradiol (2MEOE) Conjugation - Methylation COMT [2]
MR000097 Estradiol-2,3-semiquinone Estradiol-2,3-quinone Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Protein msp1 (msp1) DMEN035 Schizosaccharomyces pombe
MSP1_SCHPO
3.1.6.2
[3]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Km = 0.024 microM
UD16_HUMAN
[4]
References
1 Structure-based development of novel adenylyl cyclase inhibitors. J Med Chem. 2008 Aug 14;51(15):4456-64.
2 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol J Pharmacol Exp Ther. 2004 Jun;309(3):1093-7. doi: 10.1124/jpet.103.062505.
3 Cytochrome P450-mediated metabolism of estrogens and its regulation in human Cancer Lett. 2005 Sep 28;227(2):115-24. doi: 10.1016/j.canlet.2004.10.007.
4 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
5 Cytochrome P450-mediated metabolism of estrogens and its regulation in human. Cancer Lett. 2005 Sep 28;227(2):115-24.

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