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 |
YMCWOAZGWMZGQT-FPNLOETNSA-N |
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 |
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androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
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View more via ChEBI Ontology
16α,17β-dihydroxyandrost-4-en-3-one
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(16α,17β)-16,17-dihydroxyandrost-4-en-3-one
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IUPAC
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16α,17β-dihydroxyandrost-4-en-3-one
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UniProt
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63-01-4
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CAS Registry Number
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KEGG COMPOUND
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63-01-4
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CAS Registry Number
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ChemIDplus
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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] When measured in vitro using human placental microsomal preparations, the aromatization of 16alpha-hydroxytestosterone to estriol and androstenedione to estrone and estradiol proceeds at almost identical initial rates. Important differences between 16alpha-hydroxytestosterone and adrostenedione aromatization are evident, however. While substantial findings have implicated cytochrome P-450 in placental aromatization, the aromatizaiton of androstenedione is insensitive to CO although it is competitively inhibited by metyrapone. 16alpha-Hydroxytestosterone aromatization, in contrast, is inhibited 50-60% by CO and is strongly inhibited by metyrapone. 16alpha-hydroxytestosterone aromatization is strongly inhibited in a competitive manner by androstenedione, while 16alpha-hydroxytestosterone has essentially no effect on androstenedione aromatization, althogh at very high 16alpha-hydroxytestosterone concentrations (65 muM) and subsaturating androstenedione concentrations, 16alpha-hydroxytestosterone appears to noncomptitively inhibit androstenedione aromatization. The apparent Km for the aromatization of androstenedione is 95 nM and for 16alpha-hydroxytestosterone, 7 muM. Both androstenedione and 16alpha-hydroxytestosterone cause type I spectral perturbations associated with binding to cytochrome P-450 when added to placental microsomes; however, the deltaA390-420 is twice as great in response to saturating amounts of androstenedione than in response to 16alpha-hydroxytestosterone. If androstenedione is added to 16alpha-hydroxytestosterone, the same spectral change as that caused by androstenedione alone is expressed. The apparent spectral dissociation constant for androstenedione is 93 nM while for 16alpha-hydroxytestosterone it is 11muM; both essentially the same as the comparable apparent Kms for aromatization. The evidence suggests the presence of two aromatase P-450's in human placenta. | 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] |
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