Etiocholanolone

HCID 5880CAS 53-42-9
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Basic information

Standard SMILES
C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey
QGXBDMJGAMFCBF-BNSUEQOYSA-N
Molecular formula
C19H30O2
Average molar mass
290.4 g/mol
Monoisotopic mass
290.2245802

Overview

3alpha-hydroxy-5beta-androstan-17-one is an androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals. It has a role as a mouse metabolite and a human metabolite. It is a 17-oxo steroid, a 3alpha-hydroxy steroid and an androstanoid. It derives from a hydride of a 5beta-androstane.

Names & identifiers

Preferred name
Etiocholanolone
IUPAC
(3R,5R,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
English name
Etiocholanone
Molecular formula
C19H30O2
Molecular weight
290.44

Names & synonyms

etiocholanolone53-42-95-IsoandrosteroneAetiocholanolone5beta-AndrosteroneEtiocholan-3alpha-ol-17-one3alpha-Hydroxy-5beta-androstan-17-one3alpha-Etiocholanolone3alpha-Hydroxyetiocholan-17-one5 beta Androsterone97CGB1M48IAndrostan-17-one, 3-hydroxy-, (3alpha,5beta)-
Show more names
5BETA-ANDROSTAN-3ALPHA-OL-17-ONEC043735β-AndrosteroETIOCHOLANONEETIOCHOLANOLON5β-Androsterone(5β)-Androsterone3α-Etiocholanolone
5beta-Androstan-17-one, 3alpha-hydroxy-DTXSID001018919NSC-50908(3R,5R,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-oneJ4.146GCHEBI:28195NSC509083-alpha-hydroxy-5-beta-androstan-17-one

Database identifiers

CAS
53-42-9
PubChem CID
5880
DTXSID
DTXSID001018919
ChEMBL
CHEMBL85799
ChEBI
CHEBI:28195
UNII
97CGB1M48I
Nikkaji
J4.146G

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
21

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesChemical shift
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point152 - 154 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
148 · 148~150℃
Boiling point
392.52 °C · 392.52°C (rough estimate)
Density
0.9731 · 0.9731 (rough estimate)
refractive index
1.536 · 1.5360 (estimate)
Flash point
2 ℃ · 2℃
storage temp.
room temp

Safety & regulation

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
ridadr
UN 1648 3 / PGII
risk_code
11-20/21/22-36
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09

Chemistry & industry

Pharmacology

Metabolism/MetabolitesEtiocholanolone has known human metabolites that include Etiocholanolone glucuronide.
Cellular LocationsEndoplasmic reticulum
Metabolite PathwaysAndrostenedione Metabolism

Applications

Uses5β-Androsterone is a metabolite of Testosterone (T155000). β-Androsterone is a stereoisomer of Androsterone (A637535). 5β-Androsterone showed a weak estrogenic action.

Upstream & downstream products

Suppliers42 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
上海纽雀客生物科技有限公司13916276291 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]

Additional notes

DefinitionChEBI: An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals.

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