5-β-pregnan-3,20 dione (CHEM042076)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:49:06 UTC
Update Date2016-11-09 01:22:36 UTC
Accession NumberCHEM042076
Identification
Common Name5-β-pregnan-3,20 dione
ClassSmall Molecule
Description(5beta)-pregnane-3,20-dione, also known as 3,20-pregnanedione or 5beta-dihydroprogesterone, belongs to gluco/mineralocorticoids, progestogins and derivatives class of compounds. Those are steroids with a structure based on a hydroxylated prostane moiety. Thus, (5beta)-pregnane-3,20-dione is considered to be a steroid lipid molecule (5beta)-pregnane-3,20-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5beta)-pregnane-3,20-dione can be found in a number of food items such as opium poppy, walnut, rowal, and italian sweet red pepper, which makes (5beta)-pregnane-3,20-dione a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5BETA)-PREGNANE-3,20-dioneChEBI
3,20-PregnanedioneChEBI
5beta-DihydroprogesteroneChEBI
5beta-Pregnan-3,20-dioneChEBI
(5b)-PREGNANE-3,20-dioneGenerator
(5Β)-pregnane-3,20-dioneGenerator
5b-DihydroprogesteroneGenerator
5Β-dihydroprogesteroneGenerator
5b-Pregnan-3,20-dioneGenerator
5Β-pregnan-3,20-dioneGenerator
5-b-Pregnan-3,20 dioneGenerator
5-Β-pregnan-3,20 dioneGenerator
Chemical FormulaC21H32O2
Average Molecular Mass316.478 g/mol
Monoisotopic Mass316.240 g/mol
CAS Registry NumberNot Available
IUPAC Name(1S,2S,7R,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name(5β)-pregnane-3,20-dione
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O
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-/m1/s1
InChI KeyXMRPGKVKISIQBV-XWOJZHJZSA-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-beta-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
Polarizability37.74 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)splash10-0kkc-7920000000-b2f5e9cd5c5f21cf2c3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0259000000-c2d751219b7bd83c50f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ot-0492000000-6952daff63896df17039Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-2390000000-3a3d590dd4e3e70e717bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-154e3b1bd00054948dbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0049000000-d7397d0cc04aa171ef93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-2090000000-fef94b1e76f86c22183cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0069000000-9a5dc6a8c96deb8fb292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009t-1491000000-c085f98672eb15cc3dbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9710000000-1235b6cf9eb7965603a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-9ca213f70ddd56044addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-0091000000-20393648742744408be0Spectrum
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 IDDB07557
HMDB IDHMDB0304221
FooDB IDFDB030586
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83723
ChEBI ID30154
PubChem Compound ID92745
Kegg Compound IDC05479
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11292466
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12798477