U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26O3
Molecular Weight 302.4079
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 19-HYDROXYANDROSTENEDIONE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34CO

InChI

InChIKey=XGUHPTGEXRHMQQ-BGJMDTOESA-N
InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H26O3
Molecular Weight 302.4079
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
The role of 19-hydroxy-delta4-androstene-3,17-dione in the conversion of circulating delta4-androstene-3, 17-dione to estrone.
1976 Jul
The aromatization of androgens by primary monolayer cultures of fetal rat hypothalamus.
1977 Jan
Aromatization of delta4-androstene-3,17-dione, 19-hydroxy-delta4-androstene-3,17-dione, and 19-oxo-delta4-androstene-3,17-dione at a common catalytic site in human placental microsomes.
1977 Jan 11
Metabolism of 19-hydroxyandrostenedione in human subjects. Urinary excretion of conjugates.
1978 Mar
Amplification of the action of subthreshold doses of aldosterone by 19-hydroxyandrost-4-ene-3, 17-dione.
1979 Apr 13
A sensitive and specific in vitro bioassay method for the measurement of follicle-stimulating hormone activity.
1979 Jun
Human fatty marrow aromatizes androgen to estrogen.
1980 Aug
10 beta-propynyl-substituted steroids. Mechanism-based enzyme-activated irreversible inhibitors of estrogen biosynthesis.
1981 Feb 10
Identification of estradiol produced by Sertoli cell enriched cultures during incubation with testosterone.
1981 Jun
FSH induction of aromatase in cultured rat granulosa cells measured by a radiometric assay.
1981 May
Evidence that granulosa cell aromatase induction/activation by follicle-stimulating hormone is an androgen receptor-regulated process in-vitro.
1981 Oct
Improved in vitro bioassay of follitropin.
1982
19-hydroxyandrostenedione, a new amplifier of the action of aldosterone, in low renin essential hypertension.
1982 Apr
Effects of age and 1,4,6-androstatriene-3,17-dione on activities of hCG-induced 19-hydroxylase and aromatase of rat testes.
1982 Aug
19-hydroxyandrostenedione as a new hypertensinogenic agent.
1982 Feb
Evidence that 19-hydroxyandrostenedione is secreted by the adrenal cortex and is under the control of ACTH and the renin-angiotensin system in man.
1982 Mar 30
19-hydroxyandrostenedione and 6 beta-hydroxyandrostenedione: new steroids regulated by the renin-angiotensin system in man.
1984 Jan
Methyltrienolone (R1881) is not aromatized by placental microsomes or rat hypothalamic homogenates.
1984 May
Changes in oestrogen-synthesizing ability of preovulatory bovine follicles relative to the peak of LH.
1984 Nov
[New mineralocorticoids and mineralocorticoid-like steroids].
1984 Nov
[A comparative study of C19 steroid-induced hypertension and deoxycorticosterone acetate (DOCA)-salt hypertension].
1984 Nov 20
In vitro conversion of androgen to estrogen in amphioxus gonadal tissues.
1984 Oct
Angiotensin II induces the release of 19-hydroxyandrostenedione in man.
1985 Aug
Aromatase activity in the perinatal rat forebrain: effects of age, sex and intrauterine position.
1985 Dec
Radiometric analysis of oxidative reactions in aromatization by placental microsomes. Presence of differential isotope effects.
1985 Jan 10
Androgen aromatization and 5 alpha-reduction in ferret brain during perinatal development: effects of sex and testosterone manipulation.
1985 May
Digoxin-like immunoreactivity of 19-NOR and 19-OH-androst-4-ene-3,17-dione.
1986
P-45011 beta-dependent conversion of cortisol to cortisone, and 19-hydroxyandrostenedione to 19-oxoandrostenedione.
1986 Apr 14
Role of substrate conformational features in the stereospecificity of aromatase.
1986 Feb 11
A reevaluation of the mineralocorticoid and hypertensinogenic potential of 19-hydroxyandrostenedione.
1986 Jun
3-Methylene-substituted androgens as novel aromatization inhibitors. Evidence of a requirement for C-3 oxygen in C-19 hydroxylations.
1986 May 25
Plasma androstenedione in normotensive and hypertensive pregnancy.
1986 Nov-Dec
Enhancement of the hypertensinogenic action of 19-hydroxyandrostenedione by aromatase inhibitor, delta 1-testololactone.
1987 Dec
Metabolism of 19-methyl-substituted steroids by human placental aromatase.
1987 Dec 1
Imidazole antimycotics: selective inhibitors of steroid aromatization and progesterone hydroxylation.
1987 Jul-Sep
An improved in vitro bioassay for follicle-stimulating hormone (FSH): suitable for measurement of FSH in unextracted human serum.
1987 Sep
Formation and metabolism of 5(10)-estrene-3 beta,17 beta-diol, a novel 19-norandrogen produced by porcine granulosa cells from C19 aromatizable androgens.
1988 Aug 30
[A study of non-aromatizing androgen 19-hydroxylase in sheep adrenal].
1988 Jul 20
Synthesis of c-2, 3, 17 and 19-oxygenated androgens.
1988 Mar
Aromatase and nonaromatizing 10-demethylase activity of adrenal cortex mitochondrial P-450(11)beta.
1988 Nov 15
Direct vascular effects of 19-hydroxyandrostenedione.
1989 Apr
Plasma 19-hydroxyandrostenedione and androstenedione levels in hydatidiform moles and early pregnancies with and without hypertensive diseases.
1989 Aug
[The newly developed method of 19-OH-A as intermediate of estrone biosynthesis by GC-MS].
1989 Aug 20
Evidence for age-related change in plasma 19-hydroxyandrostenedione.
1989 Dec
Formation of 4-oestrene-3,17-dione (19-norandrostenedione) by porcine granulosa cells in vitro is inhibited by the aromatase inhibitor 4-hydroxyandrostenedione and the cytochrome P-450 inhibitors aminoglutethimide phosphate and ketoconazole.
1989 Feb
Dissociation of 19-hydroxy- 19-oxo-, and aromatizing-activities in human placental microsomes through the use of suicide substrates to aromatase.
1989 Feb
Alpha-human atrial natriuretic polypeptide inhibits 19-hydroxy-androstenedione secretion by human adrenal cells.
1989 Feb
Endocrine regulation of cytochrome P-450 in the rat brain and pituitary gland.
1989 Jul
[Non-aromatizing androgen 19-hydroxylase in human fetal organs].
1989 Jul 20
[Hypertensinogenic steroid].
1989 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:23:56 GMT 2023
Edited
by admin
on Sat Dec 16 11:23:56 GMT 2023
Record UNII
A546CQ0584
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
19-HYDROXYANDROSTENEDIONE
Systematic Name English
(8R,9S,10S,13S,14S)-10-(HYDROXYMETHYL)-13-METHYL-2,6,7,8,9,11,12,14,15,16-DECAHYDRO-1H-CYCLOPENTA(A)PHENANTHRENE-3,17-DIONE
Systematic Name English
J117.011B
Code English
4-ANDROSTENE-3,17-DIONE-19-OL
Common Name English
19-HYDROXYANDROST-4-ENE-3,17-DIONE
Systematic Name English
ANDROST-4-EN-19-OL-3,17-DIONE
Common Name English
4-ANDROSTEN-19-OL-3,17-DIONE
Common Name English
ANDROST-4-ENE-3,17-DIONE-19-OL
Common Name English
NSC-74233
Code English
19-HYDROXY-4-ANDROSTENE-3,17-DIONE
Systematic Name English
19-HAED
Common Name English
C05290
Code English
Code System Code Type Description
EPA CompTox
DTXSID80199007
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
CAS
510-64-5
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
PUBCHEM
252379
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-116-5
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
NSC
74233
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
FDA UNII
A546CQ0584
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
CHEBI
27576
Created by admin on Sat Dec 16 11:23:56 GMT 2023 , Edited by admin on Sat Dec 16 11:23:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE