Showing metabocard for 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione (BMDB0006758)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:39 UTC
Update Date2020-04-22 15:18:28 UTC
BMDB IDBMDB0006758
Secondary Accession Numbers
  • BMDB06758
Metabolite Identification
Common Name17a,21-Dihydroxy-5b-pregnane-3,11,20-trione
Description17a,21-Dihydroxy-5b-pregnane-3,11,20-trione, also known as 17a,21-dihydroxy-5b-pregnane-3,11,20-trione or 17a,21-dihydroxy-5b-pregnane-3,11,20-trione, 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. Thus, 17a,21-dihydroxy-5b-pregnane-3,11,20-trione is considered to be a steroid lipid molecule. 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione participates in a number of enzymatic reactions, within cattle. In particular, 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione can be converted into cortisone through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione can be biosynthesized from tetrahydrocortisone through the action of the enzyme aldo-keto reductase family 1 member C4. In cattle, 17a,21-dihydroxy-5b-pregnane-3,11,20-trione is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trioneChEBI
4,5beta-DihydrocortisoneChEBI
5-DihydrocortisoneChEBI
5beta-Pregnane-17alpha,21-diol-3,11,20-trioneChEBI
17Α,21-dihydroxy-5β-pregnane-3,11,20-trioneGenerator
4,5b-DihydrocortisoneGenerator
4,5Β-dihydrocortisoneGenerator
5b-Pregnane-17a,21-diol-3,11,20-trioneGenerator
5Β-pregnane-17α,21-diol-3,11,20-trioneGenerator
5 beta-DihydrocortisoneMeSH
5 beta-Pregnan-17 alpha,21-dihydroxy-3,11,20-trioneMeSH
17,21-Dihydroxy-5-beta-pregnane-3,11,20-trioneHMDB
17,21-Dihydroxy-5b-pregnane-3,11,20-trioneHMDB
4,5-b-DihydrocortisoneHMDB
4,5-beta-DihydrocortisoneHMDB
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name(1S,2S,7R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione
Traditional Namedihydrocortisone
CAS Registry Number68-54-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-15,18,22,26H,3-11H2,1-2H3/t12-,14+,15+,18-,19+,20+,21+/m1/s1
InChI KeyYCLWEYIBFOLMEM-FNLRALKVSA-N
Chemical Taxonomy
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
  • 11-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Cyclic ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 4,5-dihydrocortisone (CHEBI:18093 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05469 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030095 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP1.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.65 m³·mol⁻¹ChemAxon
Polarizability39.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2449000000-14ceeff5bbd1c13b7e36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000x-3112900000-7460382ced837d90ee15View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0009000000-1ca98bf934bbbf28c549View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005j-0039000000-d0efecc8909f14856551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2293000000-ea08c2efe1da926a70afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-ca13efcaddb50d024434View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1009000000-a0cbd44bca206fc3a34cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9076000000-a26d1916728aa73e66bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w4i-0009000000-0465f379e1cdb554bf1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-dee407a2d99539f7c10fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1079000000-59ae3fe0eed3768243f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r2-0009000000-5176fb797bda66d30605View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-0902000000-a871af6d09358801e5b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-4980000000-b0b898b8b2b5585e1af9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006758
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024062
KNApSAcK IDNot Available
Chemspider ID58997
KEGG Compound IDC05469
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65554
PDB IDNot Available
ChEBI ID18093
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available