Record Information
Version1.0
Creation date2011-09-21 00:39:16 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024061
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name11beta,21-Dihydroxy-5beta-pregnane-3,20-dione
Description11beta,21-Dihydroxy-5beta-pregnane-3,20-dione is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-5beta-pregnane-3,20-dione is the 3rd to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from Corticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to Tetrahydrocorticosterone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). [HMDB]
CAS Number566-01-8
Structure
Thumb
Synonyms
SynonymSource
11beta,21-Dihydroxy-5beta-pregnane-3,20-dioneHMDB
5beta-Pregnane-11beta,21-diol-3,20-dioneHMDB
11b,21-Dihydroxy-5b-pregnane-3,20-dionehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP2.24ALOGPS
logP2.07ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-0.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.17 m³·mol⁻¹ChemAxon
Polarizability39.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O4
IUPAC name(1S,2S,7R,10S,11S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
InChI IdentifierInChI=1S/C21H32O4/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/h12,14-17,19,22,24H,3-11H2,1-2H3/t12-,14+,15+,16?,17+,19-,20+,21+/m1/s1
InChI KeyCTTOFMJLOGMZRN-MGXYISIMSA-N
Isomeric SMILES[H][C@@]12CCC(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
Classification
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030188 )
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-MS11beta,21-Dihydroxy-5beta-pregnane-3,20-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0967000000-2bd8bffaffb50939c493Spectrum
Predicted GC-MS11beta,21-Dihydroxy-5beta-pregnane-3,20-dione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1678900000-566d143945a3f4b52be3Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0019000000-0e71fe5c93e16a4cdf43Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-1239000000-f52a428e20d7dd49be68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-3393000000-deb1166aa0a817378f80Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-4fc0c91330f741f36c93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mk-1039000000-1fc49c3cd7bc3ee2d17aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-5093000000-507f39e32c2a16004338Spectrum
NMRNot Available
ChemSpider ID24850104
ChEMBL IDNot Available
KEGG Compound IDC05475
Pubchem Compound ID44263339
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06757
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
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference