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
• #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: CHEBI:16032
  CAS Number: 53-41-8
  TTD ID: D0H5HO
  INTEDE ID: DR1916

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]
Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1)	OTZKVLVJ	CP17A_HUMAN	Biotransformations	[7]
UDP-glucuronosyltransferase 1A4	OT4PU620	UD14_HUMAN	Biotransformations	[8]
UDP-glucuronosyltransferase 2B17	OTSVIF4E	UDB17_HUMAN	Regulation of Drug Effects	[9]
UDP-glucuronosyltransferase 2B7	OT2Q71VQ	UD2B7_HUMAN	Gene/Protein Processing	[10]

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] 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. doi: 10.1016/j.abb.2003.07.003.
• [8] 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.
• [9] 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.
• [10] Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food Chem Toxicol. 2016 Apr;90:112-22.