CAS 128-23-4 | Pregnane-3,20-dione, (5β)- | CAS Number 128-23-4

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128-23-4 | Pregnane-3,20-dione, (5β)-

CAS No: 128-23-4 Catalog No: AG000XO0 MDL No:

Product Description

Catalog Number:

AG000XO0

Chemical Name:

Pregnane-3,20-dione, (5β)-

CAS Number:

128-23-4

Molecular Formula:

C21H32O2

Molecular Weight:

316.4776

IUPAC Name:

(5R,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

InChI:

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16+,17-,18+,19+,20+,21-/m1/s1

InChI Key:

XMRPGKVKISIQBV-XWOJZHJZSA-N

SMILES:

O=C1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C

UNII:

105J2Q45A0

NSC Number:

82868

Properties

Complexity:

538

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

316.24g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

316.485g/mol

Monoisotopic Mass:

316.24g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

34.1A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

4.4

Literature

Title	Journal
The VEP1 gene (At4g24220) encodes a short-chain dehydrogenase/reductase with 3-oxo-Delta4,5-steroid 5beta-reductase activity in Arabidopsis thaliana L.	Biochimie 20090401
Metabolism of neuroactive steroids in day-old chick brain.	Journal of neurochemistry 20090401
Measurement of ring A-reduced progesterone metabolites by enzyme-linked immunoassay with colorimetric detection: baseline levels of six metabolites, including pregnanolone, in male rat plasma.	Analytical chemistry 20090201
Insights into ligand-elicited activation of human constitutive androstane receptor based on novel agonists and three-dimensional quantitative structure-activity relationship.	Journal of medicinal chemistry 20081127
Antinociceptive profile of ring A-reduced progesterone metabolites in the formalin test.	Pain 20080831
The crystal structure of human Delta4-3-ketosteroid 5beta-reductase defines the functional role of the residues of the catalytic tetrad in the steroid double bond reduction mechanism.	Biochemistry 20080812
The crystal structure of progesterone 5beta-reductase from Digitalis lanata defines a novel class of short chain dehydrogenases/reductases.	The Journal of biological chemistry 20080620
Regulation of vascular tone during pregnancy: a novel role for the pregnane X receptor.	Hypertension (Dallas, Tex. : 1979) 20070201
In silico prediction of pregnane X receptor activators by machine learning approaches.	Molecular pharmacology 20070101
Circulating levels of pregnanolone isomers during the third trimester of human pregnancy.	The Journal of steroid biochemistry and molecular biology 20070101
Influence of mirtazapine on plasma concentrations of neuroactive steroids in major depression and on 3alpha-hydroxysteroid dehydrogenase activity.	Molecular psychiatry 20060301
Crystallization and preliminary crystallographic analysis of selenomethionine-labelled progesterone 5beta-reductase from Digitalis lanata Ehrh.	Acta crystallographica. Section F, Structural biology and crystallization communications 20060301
Molecular cloning and heterologous expression of progesterone 5beta-reductase from Digitalis lanata Ehrh.	Phytochemistry 20060201
3alpha-reduced neuroactive steroids and their precursors during pregnancy and the postpartum period.	Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20051101
5 Beta-dihydroprogesterone and steroid 5 beta-reductase decrease in association with human parturition at term.	Molecular human reproduction 20050701
Plasma concentrations of neuroactive steroids before and after electroconvulsive therapy in major depression.	Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050601
Metabolites of progesterone and the pregnane X receptor: a novel pathway regulating uterine contractility in pregnancy?	American journal of obstetrics and gynecology 20050401
Oestrogen and testosterone modulate the firing activity of dorsal raphe nucleus serotonergic neurones in both male and female rats.	Journal of neuroendocrinology 20050301
A PXR reporter gene assay in a stable cell culture system: CYP3A4 and CYP2B6 induction by pesticides.	Biochemical pharmacology 20041215
Insight into the mechanism of action of neuroactive steroids.	Molecular pharmacology 20040701
Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.	The Journal of endocrinology 20040701
Identification of 3beta,5beta-tetrahydroprogesterone, a progesterone metabolite, and its stimulatory action on preoptic neurons in the avian brain.	Brain research 20040508
Molecular determinants of steroid inhibition for the mouse constitutive androstane receptor.	Journal of medicinal chemistry 20031023
Specificity of human alcohol dehydrogenase 1C*2 (gamma2gamma2) for steroids and simulation of the uncompetitive inhibition of ethanol metabolism.	Chemico-biological interactions 20030201
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.	Endocrine reviews 20021001
Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin.	The Journal of biological chemistry 20010504
Developmental changes in progesterone biosynthesis and metabolism in the quail brain.	Brain research 20010413
Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands.	The Journal of biological chemistry 20000519
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.	Molecular endocrinology (Baltimore, Md.) 20000101