Details of the Drug

General Information of Drug (ID: DMJXQME)

Drug Name
Hydroxyestradiol
Synonyms
4-Hydroxy-17-beta-estradiol; 4-Hydroxyestradiol-17beta; 4-OH-Estradiol; 4-hydroxy-estradiol; 4-HYDROXYESTRADIOL; 4-hydroxyestradiol-17 beta; 4OHE2; 5976-61-4; C3ZO03450E; CHEBI:62845; MLS000069567; SMR000058747; UNII-C3ZO03450E; estra-1,3,5(10)-triene-2,4,17beta-triol; 4-Hydroxyestradiol; (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,4,17-triol; 1,3,5(10)-Estratriene-3,4,17beta-triol; 1,3,5[10]-ESTRATRIENE-3,4,17BETA-TRIOL; 3,4,17beta-estriol; 3,4,17beta-trihydroxy-1,3,5[10]-estratriene
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-3,4,17-triol
Canonical SMILES
CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4O)O
InChI
QOZFCKXEVSGWGS-ZHIYBZGJSA-N
InChIKey
1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
Cross-matching ID
PubChem CID
5282360
ChEBI ID
CHEBI:62845
CAS Number
5976-61-4
INTEDE ID
DR1976

Molecular Interaction Atlas of This Drug


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

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [2]
Alkaline phosphatase, germ cell type (ALPG) OTCIM29R PPBN_HUMAN Gene/Protein Processing [3]
ATP synthase subunit a (ATP6) OTPHOGLX ATP6_HUMAN Gene/Protein Processing [4]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [2]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Biotransformations [5]
Cytochrome c oxidase subunit 3 (COX3) OTNNGBYJ COX3_HUMAN Gene/Protein Processing [4]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Biotransformations [6]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [7]
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Gene/Protein Processing [7]
Forkhead box protein O1 (FOXO1) OTPJRB6D FOXO1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
2 Long-term exposure of 4-hydroxyestradiol induces the cancer cell characteristics via upregulating CYP1B1 in MCF-10A cells. Toxicol Mech Methods. 2019 Nov;29(9):686-692. doi: 10.1080/15376516.2019.1650146. Epub 2019 Aug 30.
3 Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells. Toxicol Lett. 2005 Jul 28;158(1):72-86. doi: 10.1016/j.toxlet.2005.02.011. Epub 2005 Apr 11.
4 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.
5 Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells. Carcinogenesis. 2008 Feb;29(2):363-70.
6 Association of the CYP1B1*3 allele with survival in patients with prostate cancer receiving docetaxel. Mol Cancer Ther. 2008 Jan;7(1):19-26. doi: 10.1158/1535-7163.MCT-07-0557. Epub 2008 Jan 9.
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.