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Showing Compound Dihydrocortisol (FDB023133)

Record Information
Version1.0
Creation date2011-09-21 00:25:09 UTC
Update date2015-07-21 06:57:32 UTC
Primary IDFDB023133
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrocortisol
DescriptionDihydrocortisol is the product of the enzyme Steroid 5-beta-reductase [EC 1.3.1.3], which catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone, testosterone, aldosterone, corticosterone and cortisol to 5-beta-reduced metabolites. A deficiency in this enzyme is associated with congenital defect in bile acid synthesis. (OMIM 235555) Dihydrocortisol is the substrate of the enzyme 3-alpha-hydroxysteroid dehydrogenase [EC:1.1.1.225 1.1.1.213 1.3.1.20 1.1.1.50], and is an iintermediate in the Bile acid biosynthesis, C21-Steroid hormone metabolism, Androgen and estrogen metabolism, and in the Metabolism of xenobiotics by cytochrome P450. (KEGG) [HMDB]
CAS Number1482-50-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
11b,17a,21-Trihydroxy-5b-pregnane-3,20-dionehmdb
5β-pregnane-11β,17α,21-triol-3,20-dioneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O5
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
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
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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-MSDihydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ac0-3659000000-d401caa0e5e4cd33ce73Spectrum
Predicted GC-MSDihydrocortisol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1501090000-2417a9d677690be1ebc9Spectrum
Predicted GC-MSDihydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDihydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009000000-1796f36bac594bc103ff2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p1-0139000000-132d9e769136246214032017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0392000000-6d131b6d30a3e0287a3a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-4cd88c3235f8488611a22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2019000000-3c3c7ef5eaf1d99b90fb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9076000000-46fac6b742ffa35f0d092017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-4a50053e3cc02927391e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-0009000000-aae740d9643ee587423a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1039000000-f7ccd0c7e04c9e3097ca2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009000000-266dd522a790c230d8da2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ta-0902000000-eaf773e5076582d8a12c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-8980000000-01a09a2f92bd6c0fa8ef2021-09-24View Spectrum
NMRNot Available
ChemSpider ID144508
ChEMBL IDNot Available
KEGG Compound IDC05471
Pubchem Compound ID164838
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03259
CRC / DFC (Dictionary of Food Compounds) IDHCN37-N:GZM99-W
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 IDS
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