Pregnanolone

HCID 31402CAS 128-20-1

Substructure search Find similar structures

Basic information

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-YZRLXODZSA-N
Molecular formula: C21H34O2
Average molar mass: 318.5 g/mol
Monoisotopic mass: 318.25588033

Overview

3alpha-hydroxy-5beta-pregnan-20-one is the 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one. It has a role as a sedative, an intravenous anaesthetic and a human metabolite. It is a 3alpha-hydroxy steroid and a 3-hydroxy-5beta-pregnan-20-one.

Names & identifiers

Preferred name: Pregnanolone
IUPAC: 1-[(3R,5R,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: Eltanolone
Molecular formula: C21H34O2
Molecular weight: 318.49

Names & synonyms

PregnanoloneELTANOLONE128-20-13alpha-Hydroxy-5beta-pregnan-20-oneEltanolonaPregnan-3alpha-ol-20-oneEltanolonumDTXSID1046342Pregnan-20-one, 3-hydroxy-, (3alpha,5beta)-(3alpha,5beta)-3-hydroxypregnan-20-oneBXO86P3XXWKabi 2213

Show more names

5β-Pregnan-3α-ol-20-oneSKF 6455Kabi2213NSC 82867Pregnanolone IIEPIPREGNANOLONE

Kabi-2213SKF-6455NSC-82867Allopregnan-3 beta-ol-20-one1-[(3R,5R,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]ethanone3 Hydroxypregnan 20 onePregnan 3alpha ol 20 one3 alpha, 5 beta-Tetrahydroprogesterone

Database identifiers

CAS: 128-20-1
PubChem CID: 31402
DTXSID: DTXSID1046342
ChEMBL: CHEMBL210952
ChEBI: CHEBI:1712
UNII: BXO86P3XXW
EC Number: 634-188-6
Nikkaji: J6.567F

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

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

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 149 °C · 149°C
alpha: 23 · D23 +59.6° (c = 0.3 in chloroform); D26 +108.5 ±1° (c = 9.23 mg/1.23 ml abs ethanol)
Boiling point: 397.64 °C · 397.64°C (rough estimate)
Density: 1.0234 · 1.0234 (rough estimate)
refractive index: 1.5344 · 1.5344 (estimate)
storage temp.: Store at RT
solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
pka: 15.12 · 15.12±0.70(Predicted)
form: Solid
color: White to Off-White
biological source: synthetic (organic)
Water Solubility: 8 mg/L · 8mg/L(room temperature)
InChI: 1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3
InChIKey: AURFZBICLPNKBZ-UHFFFAOYSA-N
SMILES: [H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2
FDA UNII: 86 P3XXW · BXO86P3XXW
NIST Chemistry Reference: 3 Alpha-hydroxy-5beta-pregnan-20-one · 3Alpha-hydroxy-5beta-pregnan-20-one(128-20-1)
UNSPSC Code: 12352202 · 12352202
NACRES: 77 · NA.77
Symbol(GHS): 8 · GHS08
Signal word: Warning
Hazard statements: 351 · H351
Precautionary statements: 281 · P281
PPE: 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: Xn
Risk Statements: 40 · 40
Safety Statements: 22 · 22-36
WGK Germany: 3 · 3
RTECS: 4384000 · TU4384000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 · Carc. 2
Toxicity: 50 in · LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

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

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesCarc. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: TU4384000
Toxicity: LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
risk_code: 40
Signal word: Warning
Symbol(GHS): GHS08
hazard_code: Xn
safety_code: 22-36
Storage Class: 11 - Combustible Solids
Hazard statements: H351
Hazard Classifications: Carc. 2
Precautionary statements: P281

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.