FComEx: 17-Hydroxyprogesterone (PC000152)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:53 UTC

Update date

2017-01-19 02:36:14 UTC

FoodComEx ID

PC000152

FoodDB Record

FDB021992

Chemical Information

Name

17-Hydroxyprogesterone

Description

It serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase. 17-Hydroxyprogesterone is a natural progestin and in pregnancy increases in the third trimester primarily due to fetal adrenal production. This hormone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase and 11β-hydroxylase, lead to a build-up of 17OHP. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17OHP. 17OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17OHP is also contributed by the placenta. [HMDB]

CAS Number

68-96-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
17-alpha-hydroxyprogesterone	hmdb
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17-Hydroxypregn-4-ene-3,20-dione	hmdb
17-Hydroxyprogesterone	hmdb
17-OH Progesterone	hmdb
17-OHP	hmdb
17a-Hydroxy-4-pregnene-3,20-dione	Generator
17a-Hydroxy-progesterone	Generator
17a-Hydroxypregn-4-ene-3,20-dione	hmdb
17a-Hydroxyprogesterone	hmdb
17alpha-Hydroxy-4-pregnene-3,20-dione	ChEBI
17alpha-Hydroxy-progesterone	ChEBI
17alpha-hydroxyprogesterone	hmdb
17α-hydroxy-4-pregnene-3,20-dione	Generator
17α-hydroxy-progesterone	Generator
17α-hydroxyprogesterone	Generator
D4-Pregnen-17a-ol-3,20-dione	hmdb
delta(4)-Pregnene-17a-ol-3,20-dione	Generator
delta(4)-Pregnene-17alpha-ol-3,20-dione	ChEBI
Gestageno	hmdb
Gestageno Gador	hmdb
Hidroxiprogesterona	ChEBI
Hydroxyprogesterone	hmdb
Hydroxyprogesteronum	ChEBI
Pregn-4-en-17a-ol-3,20-dione	hmdb
Pregn-4-ene-3,20-dione-17-ol	ChEBI
Prodix	hmdb
Prodox	hmdb
δ(4)-pregnene-17a-ol-3,20-dione	Generator
δ(4)-pregnene-17α-ol-3,20-dione	Generator

Chemical Formula

C21H30O3

IUPAC name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

InChI Identifier

InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

Isomeric SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

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