Dihydrocortisol (CHEM035506)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:49:45 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035506
Identification
Common NameDihydrocortisol
ClassSmall Molecule
DescriptionA 17alpha-hydroxy-C21-steroid that is cortisol in which the 4-5 double bond has undergone formal hydrogenation to give the corresponding 5beta- steroid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass364.476 g/mol
Monoisotopic Mass364.225 g/mol
CAS Registry Number1482-50-4
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
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 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
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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac0-3659000000-d401caa0e5e4cd33ce73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1501090000-2417a9d677690be1ebc9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009000000-1796f36bac594bc103ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p1-0139000000-132d9e76913624621403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0392000000-6d131b6d30a3e0287a3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-4cd88c3235f8488611a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2019000000-3c3c7ef5eaf1d99b90fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9076000000-46fac6b742ffa35f0d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-4a50053e3cc02927391eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-0009000000-aae740d9643ee587423aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1039000000-f7ccd0c7e04c9e3097caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009000000-266dd522a790c230d8daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ta-0902000000-eaf773e5076582d8a12cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-8980000000-01a09a2f92bd6c0fa8efSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003259
FooDB IDFDB023133
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3173
PDB IDNot Available
Wikipedia Link5α-Dihydrocortisol
Chemspider ID144508
ChEBI ID732
PubChem Compound ID164838
Kegg Compound IDC05471
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=29375009
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3793407
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3972522
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=415183
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6623065
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9535410
7. Heilmann P, Heide J, Hundertmark S, Schoneshofer M: Administration of glycyrrhetinic acid: significant correlation between serum levels and the cortisol/cortisone-ratio in serum and urine. Exp Clin Endocrinol Diabetes. 1999;107(6):370-8.
8. Rivero-Marabe JJ, Maynar-Marino JI, Garcia-de-Tiedra MP, Galan-Martin AM, Caballero-Loscos MJ, Maynar-Marino M: Determination of natural corticosteroids in urine samples from sportsmen. J Chromatogr B Biomed Sci Appl. 2001 Sep 15;761(1):77-84.
9. Schoneshofer M, Weber B, Nigam S: Increased urinary excretion of free 20 alpha- and 20 beta-dihydrocortisol in a hypercortisolemic but hypocortisoluric patient with Cushing's disease. Clin Chem. 1983 Feb;29(2):385-9.