Record Information
Version1.0
Creation date2011-09-21 00:39:19 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024064
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name11beta,17alpha,21-Trihydroxypreg-nenolone
Description11beta,17alpha,21-Trihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 11beta,17alpha,21-Trihydroxypregnenolone is the 4th to last step in the synthesis of Cortol and is converted from 17alpha,21-Dihydroxypregnenolone via the enzyme cytochrome P450 (EC:1.14.15.4). It is then converted to Cortisol via the enzyme 3beta-hydroxy-delta5-steroid dehydrogenase (EC 1.1.1.145) and the enzyme steroid delta-isomerase (EC 5.3.3.1). [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
11beta,17alpha,21-Trihydroxypreg-nenoloneHMDB
11beta,17alpha,21-TrihydroxypregnenoloneHMDB
11b,17a,21-Trihydroxypreg-nenolonehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP1.38ALOGPS
logP0.71ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.45 m³·mol⁻¹ChemAxon
Polarizability40.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H32O5
IUPAC name2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-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/h3,13-16,18,22-24,26H,4-11H2,1-2H3/t13?,14?,15?,16?,18?,19?,20?,21-/m0/s1
InChI KeyHAFVWTUQBYRPOB-QGGNSXJXSA-N
Isomeric SMILESCC12CC(O)C3C(CC=C4CC(O)CCC34C)C1CC[C@]2(O)C(=O)CO
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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0541-3359000000-db5da057c94c2a047b10JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000i-1010239000-01d0907903079ebb80e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-d6f315e61bbd67eae72aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0059000000-80e727e264ca8a26a2b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0292000000-3aa262e1ed45e0e16207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-c6648ee147e3babd9fc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btj-2029000000-37d8ba5fa07061ac854aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9087000000-1ebec2db5084d047ee8eJSpectraViewer
ChemSpider ID389583
ChEMBL IDNot Available
KEGG Compound IDC05489
Pubchem Compound ID440708
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06760
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
EnzymesNot Available
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