Showing metabocard for Dihydrocortisol (BMDB0003259)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:03:22 UTC
Update Date2020-05-11 22:30:16 UTC
BMDB IDBMDB0003259
Secondary Accession Numbers
  • BMDB03259
Metabolite Identification
Common NameDihydrocortisol
DescriptionDihydrocortisol 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, dihydrocortisol is considered to be a steroid lipid molecule. Dihydrocortisol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydrocortisol participates in a number of enzymatic reactions, within cattle. In particular, Dihydrocortisol can be converted into cortisol through the action of the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Dihydrocortisol can be biosynthesized from tetrahydrocortisol; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, dihydrocortisol is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5beta,11beta)-11,17,21-Trihydroxypregnane-3,20-dioneChEBI
11-beta,17,21-Trihydroxy-5-beta-pregnane-3,20-dioneChEBI
5beta-Pregnane-11beta,17alpha,21-triol-3,20-dioneKegg
(5b,11b)-11,17,21-Trihydroxypregnane-3,20-dioneGenerator
(5Β,11β)-11,17,21-trihydroxypregnane-3,20-dioneGenerator
11-b,17,21-Trihydroxy-5-b-pregnane-3,20-dioneGenerator
11-Β,17,21-trihydroxy-5-β-pregnane-3,20-dioneGenerator
5b-Pregnane-11b,17a,21-triol-3,20-dioneGenerator
5Β-pregnane-11β,17α,21-triol-3,20-dioneGenerator
5-beta-DihydrocortisolHMDB
11beta,17,21-Trihydroxy-5beta-pregnane-3,20-dioneHMDB
11beta,17alpha,21-Trihydroxy-5beta-pregnane-3,20-dioneHMDB
11β,17,21-Trihydroxy-5β-pregnane-3,20-dioneHMDB
11β,17α,21-Trihydroxy-5β-pregnane-3,20-dioneHMDB
5beta-DihydrocortisolHMDB
5β-DihydrocortisolHMDB
DihydrocortisolHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number1482-50-4
SMILES
[H][C@@]12CC[C@](O)(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
InChI Identifier
InChI=1S/C21H32O5/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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1
InChI KeyACSFOIGNUQUIGE-AIPUTVCKSA-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
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • 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
  • 21-hydroxy steroid (CHEBI:732 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030204 )
Ontology
StatusDetected 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
logP1.8ALOGPS
logP1.32ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.57 m³·mol⁻¹ChemAxon
Polarizability40.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003259
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023133
KNApSAcK IDNot Available
Chemspider ID144508
KEGG Compound IDC05471
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5α-Dihydrocortisol
METLIN ID3173
PubChem Compound164838
PDB IDNot Available
ChEBI ID732
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available