Details of the Drug

General Information of Drug (ID: DMITJAK)

Drug Name
ANDROSTERONE
Synonyms
androsterone; 53-41-8; Androkinine; Androtine; 5alpha-Androsterone; Atromide ICI; 3alpha-Hydroxy-5alpha-androstan-17-one; 3-Epihydroxyetioallocholan-17-one; cis-Androsterone; 3alpha-Hydroxyetioallocholan-17-one; 5alpha-Androstane-3alpha-ol-17-one; 3alpha-Hydroxy-17-androstanone; Androstanon-3-alpha-ol-17-one; 3-alpha-Hydroxy-17-androstanone; 3-alpha-Hydroxyetioallocholan-17-one; 3-alpha-Hydroxy-5-alpha-androstan-17-one; 5-alpha-Androstan-3-alpha-ol-17-one; Caswell No. 051G; Androstan-17-one, 3-hydroxy-, (3alpha,5alpha)-
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 290.4
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C19H30O2
IUPAC Name
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Canonical SMILES
C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
InChI
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChIKey
QGXBDMJGAMFCBF-HLUDHZFRSA-N
Cross-matching ID
PubChem CID
5879
ChEBI ID
CHEMBL87285
CAS Number
53-41-8
TTD ID
D0H5HO
INTEDE ID
DR1916
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gamma-aminobutyric acid receptor (GAR) TTNJYV2 NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A6 (UGT1A6) DESD26P UD16_HUMAN Substrate [2]
Aldo-keto reductase 1C3 (AKR1C3) DEGQTXO AK1C3_HUMAN Substrate [3]
Farnesol dehydrogenase (AKR1B15) DER0XCH AK1BF_HUMAN Substrate [4]
Alcohol dehydrogenase class-II (ADH4) DEOCWU3 ADH4_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Biotransformations [6]
UDP-glucuronosyltransferase 1A4 OT4PU620 UD14_HUMAN Biotransformations [7]
UDP-glucuronosyltransferase 2B17 OTSVIF4E UDB17_HUMAN Regulation of Drug Effects [8]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes. J Med Chem. 2006 Jul 27;49(15):4595-605.
2 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
3 Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7, 8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione. Biochemistry. 1998 May 12;37(19):6781-90.
4 Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates. J Biol Chem. 2015 Mar 6;290(10):6531-45.
5 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8.
6 Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.
7 UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation. Drug Metab Dispos. 2005 May;33(5):672-5. doi: 10.1124/dmd.104.002576. Epub 2005 Feb 11.
8 Isolation and characterization of a novel cDNA encoding a human UDP-glucuronosyltransferase active on C19 steroids. J Biol Chem. 1996 Sep 13;271(37):22855-62. doi: 10.1074/jbc.271.37.22855.
9 Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food Chem Toxicol. 2016 Apr;90:112-22.