Pregnenolon

Pregnenolone

HCID 8955CAS 145-13-1
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Grundinformationen

Standard-SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-N
Summenformel
C21H32O2
Durchschnittliche Molmasse
316,5 g/mol
Monoisotopische Masse
316,24023026

Überblick

Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-oxo steroid and a C21-steroid. It derives from a hydride of a pregnane.

Namen und Bezeichner

Bevorzugter Name
Pregnenolone
IUPAC
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Lokaler Name
Pregnenolon
Englischer Name
Pregnenolone
Summenformel
C21H32O2
Molmasse
316.48

Namen und Synonyme

pregnenolone145-13-13beta-Hydroxypregn-5-en-20-oneArthenoloneRegnosoneSkinostelonEneloneNatoloneBina-Skin5-Pregnen-3beta-ol-20-onedelta5-Pregnenolone5-Pregnen-3-beta-ol-20-one
Weitere Namen anzeigen
3β-Hydroxypregn-5-en-20-onePregneloneprenenolone5-pregnen-3B-ol-20-one5-pregnen-3β-ol-20-oneDELTA5-PREGNEN-3BETA-OL-20-ONE5-PregZK-5553-20-oneprenolon
PregnenolonaPregnenolonumDTXSID10365413-beta-Hydroxypregn-5-en-20-onePregn-5-en-20-one, 3-hydroxy-, (3beta)-73R90F7MQ81-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanoneDTXCID9016541

Datenbank-Bezeichner

CAS
145-13-1
PubChem CID
8955
DTXSID
DTXSID1036541
ChEMBL
CHEMBL253363
ChEBI
CHEBI:16581
UNII
73R90F7MQ8
EC Number
205-647-4
Nikkaji
J11.381F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,2
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
23

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
LogP · 2 Einträge

4.22

4.22

Solubility0.00706 mg/mL at 37 °C
Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt
188 · 188-190 °C
Siedepunkt
395.89 °C · 395.89°C (rough estimate)
Dichte
1.0382 · 1.0382 (rough estimate)
Dampfdruck
0 · 0-0Pa at 20-25℃
Brechungsindex
1.5344 · 1.5344 (estimate)
Flammpunkt
9 ℃ · 9℃

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.

Warning

H302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422
Hazard Classes and CategoriesAcute Tox. 4 (87%)

Sicherheitsdaten

wgk
3
ridadr
UN 1648 3 / PGII
hs_code
29372900
RTECS-Nr.
TU5560700
safety_code
22-24/25
Speicherklasse
3 - Flammable liquids

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, Pregn-5-en-20-on-3b-yl sulfurate, and 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone.

Tissue LocationsAdrenal Cortex
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Anwendungen · 2 Einträge

BeschreibungPregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.

VerwendenPregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20.

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