(17beta)-3-Oxoandrost-4-ene-17-carboxylic acid

HCID 99472

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Basic information

CAS: 302-97-6
Standard SMILES: C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(=O)O
InChIKey: YQACAXHKQZCEOI-UDCWSGSHSA-N
Molecular formula: C20H28O3
Average molar mass: 316.4 g/mol
Monoisotopic mass: 316.20384476

Overview

InChIKey: YQACAXHKQZCEOI-UDCWSGSHSA-N

Names & identifiers

Preferred name: (17beta)-3-Oxoandrost-4-ene-17-carboxylic acid
IUPAC: (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylic acid
English name: 4-Androsten-3-one-5-ene-17-carboxylic acid
Molecular formula: C20H28O3
Molecular weight: 316.44

Names & synonyms

302-97-6Etienic acidDTXSID00577066E3DV757KYDTXCID8031495Androst-4-ene-17-carboxylic acid, 3-oxo-, (17beta)-AOBCA4-androsten-3-one-17 beta-carboxylic acidRefChem:596826(17beta)-3-Oxoandrost-4-ene-17-carboxylic acid414-990-03-Keto-4-etiocholenic acid

Show more names

Progesterone Carboxylic AcidAD-17-Carboxylic acid3-Oxo-4-androstene-17β-carboxylic acidAD-AcidAL 3793l552.803CC 14837F-5 AcidNSC 226121

4-Androsten-3-one-5-ene-17-carboxylic acid3-Oxo-4-androstene-17beta-carboxylic acid3-oxoandrost-4-ene-17beta-carboxylic acid4-Androsten-3-one-17beta-carboxylic acidMFCD00271288CHEMBL3185181(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylic acid3-Oxo-4-Androstene-17-Carboxylicacid

Database identifiers

CAS: 302-97-6
PubChem CID: 99472
DTXSID: DTXSID0057706
ChEMBL: CHEMBL3185181
UNII: 6E3DV757KY
EC Number: 414-990-0、629-724-0
Nikkaji: J38.855F

Properties

Computed structural properties

XLogP: 3.7
Topological polar surface area: 54.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 23
Formal charge: 0
Complexity: 592

Physicochemical properties

Melting point: 260 °C · 260 °C(Solv: acetone (67-64-1); hexane (110-54-3))
Boiling point: 483.9 · 483.9±45.0 °C(Predicted)
Density: 1.17 · 1.17±0.1 g/cm3(Predicted)
solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
form: Solid
pka: 4.81 · 4.81±0.60(Predicted)
color: White to Off-White
InChI: InChI=1S/C20H28O3/c1-19-9-7-13(21)11-12(19)3-4-14-15-5-6-17(18(22)23)20(15,2)10-8-16(14)19/h11,14-17H,3-10H2,1-2H3,(H,22,23)
InChIKey: YQACAXHKQZCEOI-UHFFFAOYSA-N
SMILES: C1C2(C)C(CCC3C2CCC2(C)C3CCC2C(O)=O)=CC(=O)C1
CAS DataBase Reference: 302 · 302-97-6(CAS DataBase Reference)
FDA UNII: 6 E3DV757KY · 6E3DV757KY
Symbol(GHS): 8 · GHS08
Signal word: Warning
Hazard statements: 361 f-H413 · H361f-H413
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H361f: Suspected of damaging fertility [Warning Reproductive toxicity]

P203, P273, P280, P318, P405, and P501 (click each P-code to see the statement)

Warning

H361 (75%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P273, P280, P318, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationStatus: Active Update: 22-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28087

Hazard Classes and Categories · 4 items

Repr. 2 (75%)

Repr. 2 (33.3%)

Hazardous to the aquatic environment (chronic) - category 4

Repr. 2

Safety data

Signal word: Warning
Symbol(GHS): GHS08
Hazard statements: H361f-H413
REACH Registrations: Active

Chemistry & industry

Applications

Uses4-Androsten-3-one-5-ene-17-carboxylic acid is a testosterone based deritivative which has been used in the synthesis of a number of biologically active steroids, include finasteride and epristeride.