Showing metabocard for Tetrahydrocortisone (BMDB0000903)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:22 UTC
Update Date2020-04-22 15:05:53 UTC
BMDB IDBMDB0000903
Secondary Accession Numbers
  • BMDB00903
Metabolite Identification
Common NameTetrahydrocortisone
DescriptionTetrahydrocortisone 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. Tetrahydrocortisone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Tetrahydrocortisone can be converted into 17a,21-dihydroxy-5b-pregnane-3,11,20-trione through its interaction with the enzyme aldo-keto reductase family 1 member C4. In cattle, tetrahydrocortisone is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3a,5b)-3,17,21-Trihydroxy-pregnane-11,20-dioneHMDB
3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-oneHMDB
3a,17,21-Trihydroxy-5a-pregnane-11,20-dioneHMDB
3a,17,21-Trihydroxy-5b-pregnane-11,20-dioneHMDB
3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dioneHMDB
3alpha,17,21-Trihydroxypregnane-11,20-dioneHMDB
3b,17,21-Trihydroxy-5a-pregnane-11,20-dioneHMDB
5a-Pregnan-3b,17a,21-triol-11,20-dionHMDB
Ba 2681HMDB
Tetrahydro eHMDB
Tetrahydro-cortisoneHMDB
Tetrahydrocompound eHMDB
TetrahydrocortisonHMDB
UrocortisoneHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one
Traditional Name(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one
CAS Registry Number53-05-4
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](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/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1
InChI KeySYGWGHVTLUBCEM-SDYDLROXSA-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-hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.04ALOGPS
logP1.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.68 m³·mol⁻¹ChemAxon
Polarizability40.47 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 LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000903
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022310
KNApSAcK IDNot Available
Chemspider ID16735652
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocortisone
METLIN ID1915
PubChem Compound12444617
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBaggett, Billy; Kinsella, Ralph A., Jr.; Doisy, Edward A. Hydrolysis of conjugates of urinary corticoids with b-glucuronidase. II. The isolation and determination of tetrahydrocortisone. Journal of Biological Chemistry (1953), 203 1013-22.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available