Pregnenolone

HCID 8955CAS 145-13-1

Basic information

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
Molecular formula
C21H32O2
Average molar mass
316.5 g/mol
Monoisotopic mass
316.24023026

Overview

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.

Names & identifiers

Preferred 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
English name
Pregnenolone
Molecular formula
C21H32O2
Molecular weight
316.48

Names & synonyms

pregnenolone145-13-13beta-Hydroxypregn-5-en-20-oneArthenoloneRegnosoneSkinostelonEneloneNatoloneBina-Skin5-Pregnen-3beta-ol-20-onedelta5-Pregnenolone5-Pregnen-3-beta-ol-20-one
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
23

Experimental & physicochemical properties

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

4.22

4.22

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

Physicochemical properties

Melting point
188 · 188-190 °C
alpha
28.5 · 28.5 º (c=1, EtOH)
Boiling point
395.89 °C · 395.89°C (rough estimate)
Density
1.0382 · 1.0382 (rough estimate)
vapor pressure
0 · 0-0Pa at 20-25℃
refractive index
1.5344 · 1.5344 (estimate)

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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

Safety data

wgk
3
rtecs
TU5560700
ridadr
UN 1648 3 / PGII
hs_code
29372900
Signal word
Danger
Symbol(GHS)
GHS02,GHS07

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)
Applications · 5 items

DescriptionPregnenolone 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.

DescriptionPregnenolone is a natural steroid hormone that serves as a precursor for a wide range of steroids, including mineralocorticoids, glucocorticoids, androgens, and estrogens. Pregnenolone sulfate modulates NMDA receptor responses to exogenously applied glutamate and stimulates transient receptor potential melastatin 3 (TRPM3).

Usesglucocortcoid, antiinflammatory

UsesPregnenolone 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

General DescriptionPregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.

Suppliers50 total

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]

Additional notes

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.

Related reactions

11 records

Linked notes

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