FComEx: Dehydroepiandrosterone (PC001181)

Record Information

Version

1.0

Creation date

2018-05-02 12:10:37 UTC

Update date

2018-05-04 14:25:14 UTC

FoodComEx ID

PC001181

FoodDB Record

FDB021808

Chemical Information

Name

Dehydroepiandrosterone

Description

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS. [HMDB]. Dehydroepiandrosterone is found in many foods, some of which are summer grape, quinoa, calabash, and chinese chives.

CAS Number

53-43-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+)-Dehydroisoandrosterone	HMDB
(3-beta)-3-Hydroxyandrost-5-en-17-one	HMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one	HMDB
(3beta)-3-Hydroxy-androst-5-en-17-one	HMDB
17-Chetovis	HMDB
17-Hormoforin	HMDB
3-beta-Hydroxy-5-androsten-17-one	HMDB
3-beta-Hydroxyandrost-5-en-17-one	HMDB
3b-Hydroxy-D5-androsten-17-one	HMDB
3b-Hydroxyandrost-5-en-17-one	HMDB
3beta-Hydroxy-5-androsten-17-one	HMDB
3beta-Hydroxy-androst-5-en-17-one	HMDB
3beta-Hydroxy-D5-androsten-17-one	HMDB
3beta-Hydroxyandrost-5-en-17-one	HMDB
5-Androsten-3-beta-ol-17-one	HMDB
5-Androsten-3b-ol-17-one	HMDB
5-Androsten-3beta-ol-17-one	HMDB
5-dehydro-Epiandrosterone	HMDB
5-Dehydroepiandrosterone	HMDB
5,6-Dehydroisoandrosterone	HMDB
5,6-Didehydroisoandrosterone	HMDB
Andrestenol	HMDB
Androst-5-ene-3b-ol-17-one	HMDB
Androst-5-ene-3beta-ol-17-one	HMDB
Androsten-3beta-ol-17-one	HMDB
Androstenolone	HMDB
Astenile	HMDB
D5-Androsten-3b-ol-17-one	HMDB
D5-Androsten-3beta-ol-17-one	HMDB
Deandros	HMDB
dehydro-Epi-androsterone	HMDB
Dehydroisoandrosterone	HMDB
Diandron	HMDB
Diandrone	HMDB
Hydroxyandrostenone	HMDB
Prasterona	HMDB
Prasterone	HMDB
Prasteronum	HMDB
Prestara	HMDB
Psicosterone	HMDB
trans-Dehydroandrosterone	HMDB

Chemical Formula

C19H28O2

IUPAC name

5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3

InChI Key

FMGSKLZLMKYGDP-UHFFFAOYSA-N

Isomeric SMILES

CC12CCC3C(CC=C4CC(O)CCC34C)C1CCC2=O

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents