Record Information
Version1.0
Creation date2011-09-21 00:39:17 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024062
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione
Description17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is the second to last step in the synthesis of Cortolone and is converted from Cortisone via the enzyme Delta4-3-oxosteroid 5beta-reductase (EC 1.3.1.3). It is then converted to Urocortisone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). [HMDB]
CAS Number68-54-2
Structure
Thumb
Synonyms
SynonymSource
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
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
5 beta-Pregnan-17 alpha,21-dihydroxy-3,11,20-trioneHMDB
5 beta-DihydrocortisoneHMDB
17a,21-Dihydroxy-5b-pregnane-3,11,20-trionehmdb
17α,21-dihydroxy-5β-pregnane-3,11,20-trioneGenerator
4,5β-dihydrocortisoneGenerator
5β-pregnane-17α,21-diol-3,11,20-trioneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.91ALOGPS
logP1.71ChemAxon
logS-3.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O5
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
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
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
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
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 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
ChemSpider ID58997
ChEMBL IDNot Available
KEGG Compound IDC05469
Pubchem Compound ID65554
Pubchem Substance IDNot Available
ChEBI ID18093
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06758
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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 IDSNot Available
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
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference