(5BETA)-PREGNANE-3,20-DIONE

Identification

Name
(5BETA)-PREGNANE-3,20-DIONE
Accession Number
DB07557
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-82868 / U-2411
Categories
Not Available
UNII
105J2Q45A0
CAS number
Not Available
Weight
Average: 316.4776
Monoisotopic: 316.240230268
Chemical Formula
C21H32O2
InChI Key
XMRPGKVKISIQBV-XWOJZHJZSA-N
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
IUPAC Name
(1S,2S,7R,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNuclear receptor coactivator 1Not AvailableHuman
URetinoic acid receptor RXR-alphaNot AvailableHuman
UNuclear receptor subfamily 1 group I member 3Not AvailableHuman
U3-oxo-5-beta-steroid 4-dehydrogenaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C05479
PubChem Compound
92745
PubChem Substance
99444028
ChemSpider
83723
ChEBI
30154
ChEMBL
CHEMBL486954
HET
CI2
PDB Entries
1xv9 / 3cav

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00129 mg/mLALOGPS
logP4.06ALOGPS
logP4.19ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.34ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.88 m3·mol-1ChemAxon
Polarizability37.74 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9901
Caco-2 permeable+0.7931
P-glycoprotein substrateNon-substrate0.5427
P-glycoprotein inhibitor IInhibitor0.7728
P-glycoprotein inhibitor IIInhibitor0.5666
Renal organic cation transporterNon-inhibitor0.7576
CYP450 2C9 substrateNon-substrate0.8084
CYP450 2D6 substrateNon-substrate0.8784
CYP450 3A4 substrateSubstrate0.6958
CYP450 1A2 substrateNon-inhibitor0.866
CYP450 2C9 inhibitorNon-inhibitor0.8701
CYP450 2D6 inhibitorNon-inhibitor0.9691
CYP450 2C19 inhibitorNon-inhibitor0.8818
CYP450 3A4 inhibitorNon-inhibitor0.8767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9574
Ames testNon AMES toxic0.9348
CarcinogenicityNon-carcinogens0.8708
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity1.9780 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8602
hERG inhibition (predictor II)Non-inhibitor0.6267
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-0kkc-7920000000-b2f5e9cd5c5f21cf2c3e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-oxo-5-beta-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Progestogin-skeleton / 20-oxosteroid / 3-oxo-5-beta-steroid / Oxosteroid / 3-oxosteroid / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 20-oxo steroid, C21-steroid (CHEBI:30154) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030146)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
Gene Name
AKR1D1
Uniprot ID
P51857
Uniprot Name
3-oxo-5-beta-steroid 4-dehydrogenase
Molecular Weight
37376.615 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:23 / Updated on December 01, 2017 15:52