5a-Pregnane-3,20-dione (CHEM035567)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:53:26 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035567
Identification
Common Name5a-Pregnane-3,20-dione
ClassSmall Molecule
DescriptionA C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,20-AllopregnanedioneChEBI
3,20-Dioxo-5alpha-pregnaneChEBI
5-alpha-DihydroprogesteroneChEBI
5alpha-DihydroprogesteroneChEBI
3,20-Dioxo-5a-pregnaneGenerator
3,20-Dioxo-5α-pregnaneGenerator
5-a-DihydroprogesteroneGenerator
5-Α-dihydroprogesteroneGenerator
5a-DihydroprogesteroneGenerator
5Α-dihydroprogesteroneGenerator
5-alpha-Pregnane-3,20-dioneHMDB, MeSH
5a-Pregnan-3,20-dioneHMDB
5alpha-Pregnan-3,20-dioneHMDB
5alpha-Pregnane-3,20-dioneHMDB, MeSH
5b-Pregnane-3,20-dioneHMDB
5beta-Pregnane-3,20-dioneHMDB
Allopregnan-3,20-dioneHMDB
Pregnane-3,20-dioneHMDB
5 alpha DihydroprogesteroneMeSH, HMDB
5 beta Pregnane 3,20 dioneMeSH, HMDB
5 beta-Pregnane-3,20-dioneMeSH, HMDB
5-beta-DihydroprogesteroneMeSH, HMDB
5alpha-DHPMeSH, HMDB
3,20-Allopregnanedione, (5beta,13alpha,17alpha)-isomerMeSH, HMDB
5 alpha PregnanedioneMeSH, HMDB
5alpha DHPMeSH, HMDB
5alpha Pregnane 3,20 dioneMeSH, HMDB
5beta DHPMeSH, HMDB
5beta-DHPMeSH, HMDB
3,20 AllopregnanedioneMeSH, HMDB
3,20-Allopregnanedione, (5alpha)-isomerMeSH, HMDB
5 alpha Pregnane 3,20 dioneMeSH, HMDB
5 alpha-DihydroprogesteroneMeSH, HMDB
5 alpha-Pregnane-3,20-dioneMeSH, HMDB
5 beta DihydroprogesteroneMeSH, HMDB
5-alpha-PregnanedioneMeSH, HMDB
Chemical FormulaC21H32O2
Average Molecular Mass316.478 g/mol
Monoisotopic Mass316.240 g/mol
CAS Registry Number566-65-4
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name5a-pregnane-3,20-dione
SMILES[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI IdentifierInChI=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+/m0/s1
InChI KeyXMRPGKVKISIQBV-BJMCWZGWSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability37.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-76ef4cf96a30792f4d73Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-7151501afadd028a99ecSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-76ef4cf96a30792f4d73Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-7151501afadd028a99ecSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f76-4910000000-81546b52d59f9518cb0cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f76-4910000000-dbf8c4ca357b5f19f54dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkj-0391000000-1964b2faffc1ae5ab9b4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0159000000-fdffc096796499edd3d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p2-0492000000-3f8a5badfddf1ced4edfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-2590000000-932901e825351ef60bc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-8848319d0e10bc22bc8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0039000000-04efc7afcedbf957d0eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-1090000000-259e4f493b06ea76a0d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0069000000-c9fab448f80ee78066daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0491000000-c1e83a8609698882ba42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-3920000000-1083c653754015836eb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0049000000-e44dad0db5aa758e4dd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-0091000000-f15b1c3e520b40f7172bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003759
FooDB IDFDB023222
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link5%CE%B1-Dihydroprogesterone
Chemspider ID83782
ChEBI ID28952
PubChem Compound ID92810
Kegg Compound IDC03681
YMDB IDNot Available
ECMDB IDM2MDB005075
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15319353
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17683929
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19931389
4. Valenta, Zdenek. Steroid total synthesis and intermediates. U.S. (1975), 14 pp.