19-HYDROXYANDROSTENEDIONE

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34CO)[C@@H]1CCC2=O

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

Title	Date	PubMed
[The newly developed method of 19-OH-A as intermediate of estrone biosynthesis by GC-MS].	1989-08-20	2806683
Endocrine regulation of cytochrome P-450 in the rat brain and pituitary gland.	1989-07	2769158
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.	1989-02	2926299
Dissociation of 19-hydroxy- 19-oxo-, and aromatizing-activities in human placental microsomes through the use of suicide substrates to aromatase.	1989-02	2921872
Aromatase and nonaromatizing 10-demethylase activity of adrenal cortex mitochondrial P-450(11)beta.	1988-11-15	3264134
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.	1988-08-30	3415678
[A study of non-aromatizing androgen 19-hydroxylase in sheep adrenal].	1988-07-20	3220156
Synthesis of c-2, 3, 17 and 19-oxygenated androgens.	1988-03	3357341
Metabolism of 19-methyl-substituted steroids by human placental aromatase.	1987-12-01	3427108
Enhancement of the hypertensinogenic action of 19-hydroxyandrostenedione by aromatase inhibitor, delta 1-testololactone.	1987-12	3678133
An improved in vitro bioassay for follicle-stimulating hormone (FSH): suitable for measurement of FSH in unextracted human serum.	1987-09	3113917
Imidazole antimycotics: selective inhibitors of steroid aromatization and progesterone hydroxylation.	1987-07-01	3504059
Plasma androstenedione in normotensive and hypertensive pregnancy.	1986-11-01	3445284
A reevaluation of the mineralocorticoid and hypertensinogenic potential of 19-hydroxyandrostenedione.	1986-06	3698922
3-Methylene-substituted androgens as novel aromatization inhibitors. Evidence of a requirement for C-3 oxygen in C-19 hydroxylations.	1986-05-25	3700413
P-45011 beta-dependent conversion of cortisol to cortisone, and 19-hydroxyandrostenedione to 19-oxoandrostenedione.	1986-04-14	3707580
Role of substrate conformational features in the stereospecificity of aromatase.	1986-02-11	3955022
Digoxin-like immunoreactivity of 19-NOR and 19-OH-androst-4-ene-3,17-dione.	1986	2941812
Aromatase activity in the perinatal rat forebrain: effects of age, sex and intrauterine position.	1985-12	4084773
Angiotensin II induces the release of 19-hydroxyandrostenedione in man.	1985-08	2989318
Androgen aromatization and 5 alpha-reduction in ferret brain during perinatal development: effects of sex and testosterone manipulation.	1985-05	3987621
Radiometric analysis of oxidative reactions in aromatization by placental microsomes. Presence of differential isotope effects.	1985-01-10	3880740
[A comparative study of C19 steroid-induced hypertension and deoxycorticosterone acetate (DOCA)-salt hypertension].	1984-11-20	6526083
Changes in oestrogen-synthesizing ability of preovulatory bovine follicles relative to the peak of LH.	1984-11	6512771
[New mineralocorticoids and mineralocorticoid-like steroids].	1984-11	6397623
In vitro conversion of androgen to estrogen in amphioxus gonadal tissues.	1984-10	6541606
Studies on cytochrome P-450-dependent microsomal enzymes of testicular androgen and estrogen biosynthesis in a urodele amphibian, Necturus.	1984-07	6431195
Methyltrienolone (R1881) is not aromatized by placental microsomes or rat hypothalamic homogenates.	1984-05	6610078
19-hydroxyandrostenedione and 6 beta-hydroxyandrostenedione: new steroids regulated by the renin-angiotensin system in man.	1984-01	6708521
19-Hydroxyandrostenedione: evidence for a new class of sodium-retaining and hypertensinogenic steroids.	1983-09	6347666
19-Hydroxyandrostenedione: a potent hypertensinogenic steroid in man.	1983-07	6310235
6 beta-Hydroxyandrostenedione: evidence for a new hypertensinogenic agent.	1983	6339119
Effects of age and 1,4,6-androstatriene-3,17-dione on activities of hCG-induced 19-hydroxylase and aromatase of rat testes.	1982-08	7050537
19-hydroxyandrostenedione, a new amplifier of the action of aldosterone, in low renin essential hypertension.	1982-04	6288988
Evidence that 19-hydroxyandrostenedione is secreted by the adrenal cortex and is under the control of ACTH and the renin-angiotensin system in man.	1982-03-30	6284159
Mechanistic studies on C-19 demethylation in oestrogen biosynthesis.	1982-03-01	7092812
19-hydroxyandrostenedione as a new hypertensinogenic agent.	1982-02	7043093
Improved in vitro bioassay of follitropin.	1982	6802740
Evidence that granulosa cell aromatase induction/activation by follicle-stimulating hormone is an androgen receptor-regulated process in-vitro.	1981-10	6793349
Identification of estradiol produced by Sertoli cell enriched cultures during incubation with testosterone.	1981-06	6787345
FSH induction of aromatase in cultured rat granulosa cells measured by a radiometric assay.	1981-05	6165636
10 beta-propynyl-substituted steroids. Mechanism-based enzyme-activated irreversible inhibitors of estrogen biosynthesis.	1981-02-10	7451489
Human fatty marrow aromatizes androgen to estrogen.	1980-08	7400303
Steroid structure and function--VI. The molecular conformation of 19-hydroxy-4-androstene-3,17-dione, as an intermediate for estrogen synthetase.	1980-04	7392614
A sensitive and specific in vitro bioassay method for the measurement of follicle-stimulating hormone activity.	1979-06	463448
Amplification of the action of subthreshold doses of aldosterone by 19-hydroxyandrost-4-ene-3, 17-dione.	1979-04-13	454430
Metabolism of 19-hydroxyandrostenedione in human subjects. Urinary excretion of conjugates.	1978-03	752031
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.	1977-01-11	831774
The aromatization of androgens by primary monolayer cultures of fetal rat hypothalamus.	1977-01	830543
The role of 19-hydroxy-delta4-androstene-3,17-dione in the conversion of circulating delta4-androstene-3, 17-dione to estrone.	1976-07	947937

Patents

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:23:53 GMT 2025` Edited by `admin` on `Tue Apr 01 16:23:53 GMT 2025`
Record UNII	A546CQ0584
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

19-HYDROXYANDROSTENEDIONE

Systematic Name

English

C05290

Preferred 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

Code System Code Type Description

EPA CompTox

DTXSID80199007