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Showing Compound 5-β-pregnan-3,20 dione (FDB030586)

Record Information
Version1.0
Creation date2015-05-07 19:33:59 UTC
Update date2019-11-26 03:21:49 UTC
Primary IDFDB030586
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-β-pregnan-3,20 dione
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.
CAS Number128-23-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O2
IUPAC name(1S,2S,7R,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
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
Isomeric 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
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5-β-pregnan-3,20 dione, non-derivatized, GC-MS Spectrumsplash10-0kkc-7920000000-b2f5e9cd5c5f21cf2c3eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0259000000-c2d751219b7bd83c50f52017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ot-0492000000-6952daff63896df170392017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-2390000000-3a3d590dd4e3e70e717b2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-154e3b1bd00054948dbc2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0049000000-d7397d0cc04aa171ef932017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-2090000000-fef94b1e76f86c22183c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0069000000-9a5dc6a8c96deb8fb2922021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009t-1491000000-c085f98672eb15cc3dbb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9710000000-1235b6cf9eb7965603a22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e6642021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-9ca213f70ddd56044add2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-0091000000-20393648742744408be02021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference