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
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.91ALOGPS
logP1.71ChemAxon
logS-3.4ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2449000000-14ceeff5bbd1c13b7e36Spectrum
Predicted GC-MS17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-3112900000-7460382ced837d90ee15Spectrum
Predicted GC-MS17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0009000000-1ca98bf934bbbf28c5492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005j-0039000000-d0efecc8909f148565512017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2293000000-ea08c2efe1da926a70af2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-ca13efcaddb50d0244342017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1009000000-a0cbd44bca206fc3a34c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9076000000-a26d1916728aa73e66bf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w4i-0009000000-0465f379e1cdb554bf1a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-dee407a2d99539f7c10f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1079000000-59ae3fe0eed3768243f62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r2-0009000000-5176fb797bda66d306052021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-0902000000-a871af6d09358801e5b62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-4980000000-b0b898b8b2b5585e1af92021-09-25View Spectrum
NMRNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference