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Showing Compound 21-Hydroxy-5beta-pregnane-3,11,20-trione (FDB024060)

Record Information
Version1.0
Creation date2011-09-21 00:39:15 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024060
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name21-Hydroxy-5beta-pregnane-3,11,20-trione
Description21-Hydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 21-Hydroxy-5beta-pregnane-3,11,20-trione is the second to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from 11-Dehydrocorticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). [HMDB]
CAS Number10417-86-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3alpha-Hydroxy-5beta-pregnane-20-oneHMDB
21-Hydroxy-5beta-pregnane-3,11,20-trioneHMDB
21-Hydroxy-5b-pregnane-3,11,20-trionehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP2.63ALOGPS
logP2.45ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.25 m³·mol⁻¹ChemAxon
Polarizability38.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H30O4
IUPAC name(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione
InChI IdentifierInChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1
InChI KeyZDUVZJUTJOBJHS-HNEBDTNWSA-N
Isomeric SMILES[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
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-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Predicted GC-MS21-Hydroxy-5beta-pregnane-3,11,20-trione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fki-1988000000-fba247baf630a7210351Spectrum
Predicted GC-MS21-Hydroxy-5beta-pregnane-3,11,20-trione, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-2639300000-c9ca38b4ccbbd8f2986eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-24f7d25b96d058ce27ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0139000000-14964e5f329435527649Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-3293000000-fdc80d45785ab54b814fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-804a5ed2772af86708b7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05p2-1029000000-b83f2a0acc0792e5262bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5092000000-c68952d24a29d9931c16Spectrum
NMRNot Available
ChemSpider ID24850108
ChEMBL IDNot Available
KEGG Compound IDC05477
Pubchem Compound ID44263345
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06756
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
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference