CAS 516-55-2 Isopregnanolone (HCID 92787)

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Basic information

CAS: 516-55-2
Standard SMILES: CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: AURFZBICLPNKBZ-FZCSVUEKSA-N
Molecular formula: C21H34O2
Average molar mass: 318.5 g/mol
Monoisotopic mass: 318.25588033

Overview

3beta-hydroxy-5alpha-pregnan-20-one is a 3-hydroxy-5alpha-pregnan-20-one.

Names & identifiers

Preferred name: Isopregnanolone
IUPAC: 1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
English name: Alloepipregnanolone
Molecular formula: C21H34O2
Molecular weight: 318.49

Names & synonyms

Isopregnanolone516-55-2Sepranolone5alpha-Pregnan-3beta-ol-20-oneAllopregnan-3beta-ol-20-oneIsoallopregnanolone3beta-Hydroxy-5alpha-pregnan-20-oneSepranolona3-beta-Hydroxy-5-alpha-pregnan-20-one3P8Z6V53MUNSC-97078UC1010

Show more names

3β-hydroxy-5α-pregnan-20-oneZulressoAlloepipregnanoloneTetrahydroprogesterone3-beta-allopregnanolone5A-PREGNAN-3BETA-OL-20-ONEu0949NSC 97078

UC-1010(3beta,5alpha)-3-hydroxypregnan-20-oneCHEBI:11909U-0949DTXSID001023710sepranolonumRefChem:1087665DTXCID401508027

Database identifiers

CAS: 516-55-2
PubChem CID: 92787
DTXSID: DTXSID001023710
ChEMBL: CHEMBL2057301

Properties

Computed structural properties

XLogP: 4.9
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 23
Formal charge: 0
Complexity: 500

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point194.5 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 200 ℃ · 200℃
alpha: 27 · D27 +91.2° (c = 0.4 in ethanol)
Boiling point: 431.2 · 431.2±18.0 °C(Predicted)
Density: 1.1 g/cm3 · 1.1 g/cm3
storage temp.: Refrigerator
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Solid

Safety & regulation

Safety data

rtecs: TU4383200
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335-H413
Precautionary statements: P261-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Applications · 3 items

DescriptionAllopregnanolone is a neuroactive metabolite of progesterone. It is a potent positive allosteric modulator of the action of GABA on the GABAA receptor.

UsesIsopregnanolone is used in the preparation of antimicrobial and anti-leukemic steroids. Intermediate.