Details of the Drug

General Information of Drug (ID: DMSE8NU)

Drug Name
4-ANDROSTENE-3-17-DIONE
Synonyms
Androstenedione; androstenedione; 4-Androstene-3,17-dione; Androst-4-ene-3,17-dione; 1963/5/8; 4-Androstenedione; Androtex; 3,17-Dioxoandrost-4-ene; delta-4-Androstenedione; SKF 2170; Fecundin; delta-4-Androsten-3,17-dione; delta-4-Androstene-3,17-dione; Androstendione; 4-Androsten-3,17-dione; NSC 9563; delta-(sup4)-Androsten-3,17-dione; delta(sup 4)-Androstene-3,17-dione; UNII-409J2J96VR; 17-Ketotestosterone; d4-androstenedione; CHEBI:16422; Androstenedione [JAN]; HSDB 7335; EINECS 200-554-5; MLS000028510; NSC9563; ANDROSTENEDIONE
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) 286.4
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C19H26O2
IUPAC Name
(8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Canonical SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
InChI
InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChIKey
AEMFNILZOJDQLW-QAGGRKNESA-N
Cross-matching ID
PubChem CID
6128
ChEBI ID
CHEBI:16422
CAS Number
63-05-8
UNII
409J2J96VR
DrugBank ID
DB01536
TTD ID
D0M8RO
VARIDT ID
DR00943
INTEDE ID
DR0116

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [1]
Dihydrodiol dehydrogenase type I (AKR1C3) TT5ZWB6 AK1C3_HUMAN Inhibitor [2]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1) TTIWB6L DHB1_HUMAN Inhibitor [2]
Hydroxysteroid dehydrogenase 3-beta (HSD3B) TTZT9R2 3BHS1_HUMAN ; 3BHS2_HUMAN Agonist [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Testicular 17-beta-hydroxysteroid dehydrogenase (HSD17B3)
Main DME 		DEX8J7E DHB3_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase type 2 (HSD17B2) OT3K7HY5 DHB2_HUMAN Biotransformations [4]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1) OTNAZVKB 3BHS1_HUMAN Biotransformations [4]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Regulation of Drug Effects [5]
Aldo-keto reductase family 1 member D1 (AKR1D1) OTBDJ6RL AK1D1_HUMAN Biotransformations [6]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Regulation of Drug Effects [7]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [8]
CREB-binding protein (CREBBP) OTPA4QGM CBP_HUMAN Gene/Protein Processing [9]
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Biotransformations [10]
Dehydrogenase/reductase SDR family member 7 (DHRS7) OTV729DT DHRS7_HUMAN Biotransformations [11]
Glutathione S-transferase A1 (GSTA1) OTA7K5XA GSTA1_HUMAN Biotransformations [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dihydrodiol dehydrogenase type I (AKR1C3) DTT AKR1C3 4.06E-01 1.39 0.74
Testicular 17-beta-hydroxysteroid dehydrogenase (HSD17B3) DME HSD17B3 3.54E-02 2.20E-01 3.98E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
2 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
3 17beta-hydroxysteroid dehydrogenase-3 deficiency: a rare endocrine cause of male-to-female sex reversal. Gynecol Endocrinol. 2006 Sep;22(9):488-94.
4 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.
5 Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
6 Human and murine steroid 5-reductases (AKR1D1 and AKR1D4): insights into the role of the catalytic glutamic acid. Chem Biol Interact. 2019 May 25;305:163-170. doi: 10.1016/j.cbi.2019.03.025. Epub 2019 Mar 28.
7 A comparison of two human cell lines and two rat gonadal cell primary cultures as in vitro screening tools for aromatase modulation. Toxicol In Vitro. 2012 Feb;26(1):107-18.
8 Localization of breast cancer resistance protein (Bcrp) in endocrine organs and inhibition of its transport activity by steroid hormones. Cell Tissue Res. 2012 Aug;349(2):551-63. doi: 10.1007/s00441-012-1417-5. Epub 2012 May 13.
9 ErbB receptor signaling and therapeutic resistance to aromatase inhibitors. Clin Cancer Res. 2006 Feb 1;12(3 Pt 2):1008s-1012s. doi: 10.1158/1078-0432.CCR-05-2352.
10 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.
11 Biochemical properties of human dehydrogenase/reductase (SDR family) member 7. Chem Biol Interact. 2014 Jan 25;207:52-7. doi: 10.1016/j.cbi.2013.11.003. Epub 2013 Nov 16.
12 Human glutathione S-transferase A (GSTA) family genes are regulated by steroidogenic factor 1 (SF-1) and are involved in steroidogenesis. FASEB J. 2013 Aug;27(8):3198-208. doi: 10.1096/fj.12-222745. Epub 2013 May 6.