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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P28845 Gene ID: 3290.0 Gene Symbol: HSD11B1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20016029 |
1.2 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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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 |
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7-Alpha-hydroxytestosterone in seminiferous tubules of rat testis. | 1983 Mar |
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Studies on the kinetics of the interaction of 7 alpha-hydroxytestosterone with the steroid 5 alpha-reductase. | 1985 Feb |
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Effects of caloric restriction on expression of testicular cytochrome P450 enzymes associated with the metabolic activation of carcinogens. | 1996 Nov 1 |
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Cultures with cryopreserved hepatocytes: applicability for studies of enzyme induction. | 2000 Feb 15 |
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7alpha-hydroxytestosterone affects 1 beta-hydroxysteroid dehydrogenase 1 direction in rat Leydig cells. | 2010 Feb |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20016029
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
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admin
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Edited
Sat Dec 16 08:07:01 GMT 2023
by
admin
on
Sat Dec 16 08:07:01 GMT 2023
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Record UNII |
6VJJ9I1FHR
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Record Status |
Validated (UNII)
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Record Version |
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