CHEBI:34172 - 16α-hydroxytestosterone

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ChEBI Name 16α-hydroxytestosterone
ChEBI ID CHEBI:34172
ChEBI ASCII Name 16alpha-hydroxytestosterone
Definition A C19-steroid that is testosterone in which the hydrogen at the 16α position has been replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000005764327
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Formula C19H28O3
Net Charge 0
Average Mass 304.425
Monoisotopic Mass 304.20384
InChI InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15+,16-,17+,18+,19+/m1/s1
InChIKey YMCWOAZGWMZGQT-FPNLOETNSA-N
SMILES C1C(C=C2[C@](C1)([C@@]3([C@@](CC2)([C@@]4([H])[C@@](CC3)(C)[C@H]([C@@H](C4)O)O)[H])[H])C)=O
Roles Classification
Biological Role(s): androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 16α-hydroxytestosterone (CHEBI:34172) has functional parent testosterone (CHEBI:17347)
16α-hydroxytestosterone (CHEBI:34172) has role androgen (CHEBI:50113)
16α-hydroxytestosterone (CHEBI:34172) is a 16α-hydroxy steroid (CHEBI:16799)
16α-hydroxytestosterone (CHEBI:34172) is a 17β-hydroxy steroid (CHEBI:35343)
16α-hydroxytestosterone (CHEBI:34172) is a 3-oxo-Δ4 steroid (CHEBI:47909)
16α-hydroxytestosterone (CHEBI:34172) is a androstanoid (CHEBI:50402)
16α-hydroxytestosterone (CHEBI:34172) is a C19-steroid (CHEBI:131621)
16α-hydroxytestosterone (CHEBI:34172) is a diol (CHEBI:23824)
16α-hydroxytestosterone (CHEBI:34172) is a secondary alcohol (CHEBI:35681)
IUPAC Name
16α,17β-dihydroxyandrost-4-en-3-one
Synonyms Sources
(16α,17β)-16,17-dihydroxyandrost-4-en-3-one IUPAC
16α,17β-dihydroxyandrost-4-en-3-one UniProt
Manual Xref Database
C14600 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
63-01-4 CAS Registry Number KEGG COMPOUND
63-01-4 CAS Registry Number ChemIDplus
Citations
Canick JA, Ryan KJ (1976)
Cytochrome P-450 and the aromatization of 16alpha-hydroxytestosterone and androstenedione by human placental microsomes.
Molecular and cellular endocrinology 6, 105-115 [PubMed:1001810]
[show Abstract]
Lisboa BP, Gustafsson JA (1970)
Studies on the metabolism of steroids in the foetus. Biosynthesis of 16alpha-hydroxytestosterone in the human foetal liver.
Endokrinologie 56, 262-269 [PubMed:5498128]
NEHER R, STARK G (1961)
[Detection of corticosteroids in the human placenta and isolation of 16alpha-hydroxytestosterone].
Experientia 17, 510-512 [PubMed:14478807]
Last Modified
10 April 2018