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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O3
Molecular Weight 304.4238
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7.ALPHA.-HYDROXYTESTOSTERONE

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])[C@H](O)CC4=CC(=O)CC[C@]34C

InChI

InChIKey=RNCGWYKXAJCOLD-JUKXBMAYSA-N
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15+,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H28O3
Molecular Weight 304.4238
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

7α-hydroxytestosterone is an androstanoid that is testosterone substituted by a α-hydroxy group at position 7. It is a polar testosterone metabolite first identified by incubation of testes of adult rats with testosterone. Cytochrome P450 2A1 (CYP2A1) present in rat testis catalyzes the metabolism of testosterone into 7α-hydroxytestosterone. 7α-hydroxytestosterone is also a natural product found in Daphnia magna exposed to the biocide tributyltin. It has been reported to inhibit steroidogenic enzymes in testis including 5α-reductase and 3α-hydroxysteroid dehydrogenase (17β-HSD3). In the developing rat testis and Leydig cells 7 alpha-hydroxytestosterone effected the activity of 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1), enzyme that interconverts active corticosterone and inactive 11-dehydrocorticosterone. It competitively suppressed 11 beta-HSD1 oxidase and reductase activities in rat testis microsome preparations and regulated the direction of 11 beta-HSD1 activity in rat Leydig cells. 7-hydroxytestosterone does not influence rat seminal vesicle weight nor does it induce thermogenic enzymes. It was reported that 7a-hydroxytestosterone has no androgenic activity as measured by its lack of effect on maintenance of acid phosphatase in the prostate of castrated rats.

Originator

Curator's Comment: Incubation of testes of adult rats with testosterone yield rather important amounts of a very polar metabolite which was identified as 7a-hydroxytestosterone. The identification of the metabolite is based on chromatography, spectrophotometry, fluorimetry, counter current distribution and NMR spectrometry.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28845
Gene ID: 3290.0
Gene Symbol: HSD11B1
Target Organism: Homo sapiens (Human)
1.2 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Hydroxylation of testosterone at carbons 1, 2, 6, 7, 15 and 16 by the hepatic microsomal fraction from adult female C57BL/6J mice.
1975 Sep 1
7-Alpha-hydroxytestosterone in seminiferous tubules of rat testis.
1983 Mar
Studies on the kinetics of the interaction of 7 alpha-hydroxytestosterone with the steroid 5 alpha-reductase.
1985 Feb
Effects of caloric restriction on expression of testicular cytochrome P450 enzymes associated with the metabolic activation of carcinogens.
1996 Nov 1
Cultures with cryopreserved hepatocytes: applicability for studies of enzyme induction.
2000 Feb 15
7alpha-hydroxytestosterone affects 1 beta-hydroxysteroid dehydrogenase 1 direction in rat Leydig cells.
2010 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Effects of 10nM – 0.1 mM 7 alpha-hydroxytestosterone (7HT) on 11β-HSD1 oxidase and reductase activities in rat testis microsome preparations were examined. At 100 nm and higher concentrations, 7HT significantly switched 11 beta-HSD1 oxidoreductase activities toward reductase.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:07:01 GMT 2023
Edited
by admin
on Sat Dec 16 08:07:01 GMT 2023
Record UNII
6VJJ9I1FHR
Record Status Validated (UNII)
Record Version
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Name Type Language
7.ALPHA.-HYDROXYTESTOSTERONE
Common Name English
ANDROST-4-EN-3-ONE, 7,17-DIHYDROXY-, (7.ALPHA.,17.BETA.)-
Systematic Name English
7.ALPHA.,17.BETA.-DIHYDROXYANDROST-4-EN-3-ONE
Systematic Name English
(7.ALPHA.,17.BETA.)-7,17-DIHYDROXYANDROST-4-EN-3-ONE
Systematic Name English
ANDROST-4-EN-3-ONE, 7.ALPHA.,17.BETA.-DIHYDROXY-
Systematic Name English
NSC-51179
Code English
Code System Code Type Description
NSC
51179
Created by admin on Sat Dec 16 08:07:01 GMT 2023 , Edited by admin on Sat Dec 16 08:07:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID50977536
Created by admin on Sat Dec 16 08:07:01 GMT 2023 , Edited by admin on Sat Dec 16 08:07:01 GMT 2023
PRIMARY
FDA UNII
6VJJ9I1FHR
Created by admin on Sat Dec 16 08:07:01 GMT 2023 , Edited by admin on Sat Dec 16 08:07:01 GMT 2023
PRIMARY
CAS
62-83-9
Created by admin on Sat Dec 16 08:07:01 GMT 2023 , Edited by admin on Sat Dec 16 08:07:01 GMT 2023
PRIMARY
PUBCHEM
65541
Created by admin on Sat Dec 16 08:07:01 GMT 2023 , Edited by admin on Sat Dec 16 08:07:01 GMT 2023
PRIMARY