Pregnanolone

HCID 31402CAS 128-20-1

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Grundinformationen

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
Summenformel: C21H34O2
Durchschnittliche Molmasse: 318,5 g/mol
Monoisotopische Masse: 318,25588033

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Englischer Name: Eltanolone
Summenformel: C21H34O2
Molmasse: 318.49

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,9
Polarare Oberfläche (TPSA): 37,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 23
Formalladung: 0
Komplexität: 500

Experimentelle und physikochemische Eigenschaften

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

Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt: 149 °C · 149°C
Siedepunkt: 397.64 °C · 397.64°C (rough estimate)
Dichte: 1.0234 · 1.0234 (rough estimate)
Brechungsindex: 1.5344 · 1.5344 (estimate)
storage temp.: Store at RT
Löslichkeit: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
pka: 15.12 · 15.12±0.70(Predicted)
Aggregatzustand: Solid
Farbe: White to Off-White
Biologische Quelle: synthetic (organic)
Wasserlöslichkeit: 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
NIST chemische Informationen: 3 Alpha-hydroxy-5beta-pregnan-20-one · 3Alpha-hydroxy-5beta-pregnan-20-one(128-20-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesCarc. 2 (100%)

Sicherheitsdaten

wgk: 3
RTECS-Nr.: TU4384000
risk_code: 40
Toxizität: LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
hazard_code: Xn
safety_code: 22-36
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Carc. 2

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 1 Eintrag

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.