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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O2
Molecular Weight 316.4776
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,20-PREGNANEDIONE

SMILES

CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=XMRPGKVKISIQBV-XWOJZHJZSA-N
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

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism of neuroactive steroids in day-old chick brain.
2009-04
The VEP1 gene (At4g24220) encodes a short-chain dehydrogenase/reductase with 3-oxo-Delta4,5-steroid 5beta-reductase activity in Arabidopsis thaliana L.
2009-04
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.
2009-02-01
Antinociceptive profile of ring A-reduced progesterone metabolites in the formalin test.
2008-08-31
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.
2008-08-12
The crystal structure of progesterone 5beta-reductase from Digitalis lanata defines a novel class of short chain dehydrogenases/reductases.
2008-06-20
Regulation of vascular tone during pregnancy: a novel role for the pregnane X receptor.
2007-02
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007-01
Circulating levels of pregnanolone isomers during the third trimester of human pregnancy.
2006-09-27
Crystallization and preliminary crystallographic analysis of selenomethionine-labelled progesterone 5beta-reductase from Digitalis lanata Ehrh.
2006-03-01
Influence of mirtazapine on plasma concentrations of neuroactive steroids in major depression and on 3alpha-hydroxysteroid dehydrogenase activity.
2006-03
Molecular cloning and heterologous expression of progesterone 5beta-reductase from Digitalis lanata Ehrh.
2006-02
3alpha-reduced neuroactive steroids and their precursors during pregnancy and the postpartum period.
2005-11
5 Beta-dihydroprogesterone and steroid 5 beta-reductase decrease in association with human parturition at term.
2005-07
Plasma concentrations of neuroactive steroids before and after electroconvulsive therapy in major depression.
2005-06
Metabolites of progesterone and the pregnane X receptor: a novel pathway regulating uterine contractility in pregnancy?
2005-04
Oestrogen and testosterone modulate the firing activity of dorsal raphe nucleus serotonergic neurones in both male and female rats.
2005-03
A PXR reporter gene assay in a stable cell culture system: CYP3A4 and CYP2B6 induction by pesticides.
2004-12-15
Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.
2004-07
Insight into the mechanism of action of neuroactive steroids.
2004-07
Identification of 3beta,5beta-tetrahydroprogesterone, a progesterone metabolite, and its stimulatory action on preoptic neurons in the avian brain.
2004-05-08
Specificity of human alcohol dehydrogenase 1C*2 (gamma2gamma2) for steroids and simulation of the uncompetitive inhibition of ethanol metabolism.
2003-02-01
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002-10
Developmental changes in progesterone biosynthesis and metabolism in the quail brain.
2001-04-13
Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands.
2000-05-19
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
2000-01
Name Type Language
NSC-82868
Preferred Name English
3,20-PREGNANEDIONE
MI  
Systematic Name English
3,20-PREGNANEDIONE [MI]
Common Name English
PREGNANE-3,20-DIONE, (5.BETA.)-
Systematic Name English
U-2411
Code English
5.BETA.-PREGNAN-3,20-DIONE
Systematic Name English
5.BETA.-DIHYDROPROGESTERONE
Systematic Name English
Code System Code Type Description
CHEBI
30154
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
WIKIPEDIA
5?-Dihydroprogesterone
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
MERCK INDEX
m9116
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY Merck Index
CAS
128-23-4
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
DRUG BANK
DB07557
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
NSC
82868
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID00878589
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
FDA UNII
105J2Q45A0
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY
PUBCHEM
92745
Created by admin on Mon Mar 31 23:04:23 GMT 2025 , Edited by admin on Mon Mar 31 23:04:23 GMT 2025
PRIMARY