Details of the Drug

General Information of Drug (ID: DMM9Z0B)

Drug Name
2-hydroxy-17beta-estradiol
Synonyms
2-Hydroxyestradiol; 2-OH-Estradiol; 362-05-0; 2-hydroxy-estradiol; 2-OH-E2; (17beta)-Estra-1,3,5(10)-triene-2,3,17-triol; UNII-AYU2L67YUU; Estra-1,3,5(10)-triene-2,3,17beta-triol; CHEBI:28744; NSC 61711; AYU2L67YUU; 2-Hydroxy-17; MLS000069506; CHEMBL467987; DILDHNKDVHLEQB-XSSYPUMDSA-N; ESTRA-1,3,5(10)-TRIENE-2,3,17-beta-TRIOL; SMR000058615; ECS; CCRIS 8709; 2bw7
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.4
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C18H24O3
IUPAC Name
(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,3,17-triol
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)O)O
InChI
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
Cross-matching ID
PubChem CID
247304
ChEBI ID
CHEBI:28744
CAS Number
362-05-0
DrugBank ID
DB07706
TTD ID
D00PZE
INTEDE ID
DR1974

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenylate cyclase (ADCY) TT2QM9D NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A6 (UGT1A6)
Main DME 		DESD26P UD16_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP synthase subunit a (ATP6) OTPHOGLX ATP6_HUMAN Gene/Protein Processing [3]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Biotransformations [4]
Cytochrome c oxidase subunit 3 (COX3) OTNNGBYJ COX3_HUMAN Gene/Protein Processing [3]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Biotransformations [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Biotransformations [6]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Biotransformations [6]
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Gene/Protein Processing [7]
Forkhead box protein O1 (FOXO1) OTPJRB6D FOXO1_HUMAN Gene/Protein Processing [7]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [7]
Insulin-like growth factor-binding protein 1 (IGFBP1) OT6UQV2K IBP1_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Structure-based development of novel adenylyl cyclase inhibitors. J Med Chem. 2008 Aug 14;51(15):4456-64.
2 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
3 Enhanced levels of several mitochondrial mRNA transcripts and mitochondrial superoxide production during ethinyl estradiol-induced hepatocarcinogenesis and after estrogen treatment of HepG2 cells. Carcinogenesis. 1998 Dec;19(12):2187-93. doi: 10.1093/carcin/19.12.2187.
4 Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol Pharmacol. 2001 Feb;59(2):393-402. doi: 10.1124/mol.59.2.393.
5 Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells. Carcinogenesis. 2004 Oct;25(10):2005-13. doi: 10.1093/carcin/bgh183. Epub 2004 May 13.
6 Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals. Drug Metab Dispos. 2006 Sep;34(9):1606-14.
7 Catechol estrogens induce proliferation and malignant transformation in prostate epithelial cells. Toxicol Lett. 2013 Jul 18;220(3):247-58. doi: 10.1016/j.toxlet.2013.05.002. Epub 2013 May 15.
8 Tryptophan and kynurenine stimulate human decidualization via activating Aryl hydrocarbon receptor: Short title: Kynurenine action on human decidualization. Reprod Toxicol. 2020 Sep;96:282-292. doi: 10.1016/j.reprotox.2020.07.011. Epub 2020 Aug 8.