FComEx: Androsterone (PC000338)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:01 UTC

Update date

2017-01-19 02:36:20 UTC

FoodComEx ID

PC000338

FoodDB Record

FDB021881

Chemical Information

Name

Androsterone

Description

Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133) [HMDB]

CAS Number

53-41-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3alpha,5alpha)-3-hydroxy-Androstan-17-one	hmdb
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one	hmdb
3-alpha-Hydroxy-17-androstanone	hmdb
3-alpha-Hydroxy-5-alpha-androstan-17-one	hmdb
3-alpha-Hydroxy-5-alpha-androstane-17-one	hmdb
3-alpha-hydroxy-5alpha-Androstan-17-one	hmdb
3-alpha-Hydroxyetioallocholan-17-one	hmdb
3-Epihydroxyetioallocholan-17-one	hmdb
3-hydroxy-(3-alpha,5-alpha)-Androstan-17-one	hmdb
3-Hydroxyandrostan-17-one	hmdb
3a-Hydroxyetioallocholan-17-one	hmdb
3alpha-Hydroxy-17-androstanone	hmdb
3alpha-Hydroxy-5alpha-androstan-17-one	hmdb
3alpha-Hydroxyetioallocholan-17-one	hmdb
5-alpha-Androstan-3-alpha-ol-17-one	hmdb
5-alpha-Androstane-3alpha-ol-17-one	hmdb
5-alpha-Androsterone	hmdb
5a-Androstan-3a-ol-17-one	hmdb
5a-Androstane-3a-ol-17-one	hmdb
5a-Androsterone	hmdb
5alpha-Androstane-3alpha-ol-17-one	hmdb
5alpha-Androsterone	hmdb
Androkinine	hmdb
Androstanon-3-alpha-ol-17-one	hmdb
Androsterone	hmdb
Androtine	hmdb
Atromide ICI	hmdb
cis-Androsterone	hmdb

Chemical Formula

C19H30O2

IUPAC name

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

InChI Identifier

InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13?,14-,15-,16-,18-,19-/m0/s1

InChI Key

QGXBDMJGAMFCBF-XYQQMQERSA-N

Isomeric SMILES

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

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

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