FComEx: Pregnenolone (PC000378)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:22 UTC

Update date

2017-01-19 02:36:21 UTC

FoodComEx ID

PC000378

FoodDB Record

FDB021920

Chemical Information

Name

Pregnenolone

Description

Pregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809) [HMDB]. Pregnenolone is found in many foods, some of which are common wheat, yellow bell pepper, oval-leaf huckleberry, and fenugreek.

CAS Number

145-13-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3b)-3-hydroxy-Pregn-5-en-20-one	hmdb
3-hydroxypregn-5-en-20-one	hmdb
3b-Hydroxypregn-5-en-20-one	hmdb
3beta-Hydroxypregn-5-en-20-one	hmdb
5-Pregnen-3b-ol-20-one	hmdb
5-Pregnen-3beta-ol-20-one	hmdb
Natolone	hmdb
Pregn-5-en-3b-ol-20-one	hmdb
Pregn-5-ene-3b-ol-20-one	hmdb
Pregnetan	hmdb
Pregneton	hmdb
Pregnolon	hmdb
Prenolon	hmdb
Regnosone	hmdb
Skinostelon	hmdb

Chemical Formula

C21H32O2

IUPAC name

1-[(1S,2R,5R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

InChI Identifier

InChI=1S/C21H32O2/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/h4,15-19,23H,5-12H2,1-3H3/t15-,16?,17-,18+,19+,20+,21-/m1/s1

InChI Key

ORNBQBCIOKFOEO-STZXPNGSSA-N

Isomeric SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])C2CC=C2C[C@H](O)CC[C@]12C

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents