Record Information
Version3.6
Creation Date2008-08-06 15:19:57 UTC
Update Date2013-02-09 00:15:16 UTC
HMDB IDHMDB06760
Secondary Accession Numbers
  • HMDB06761
Metabolite Identification
Common Name11b,17a,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).
Structure
Thumb
Synonyms
  1. 11beta,17alpha,21-Trihydroxypreg-nenolone
  2. 11beta,17alpha,21-Trihydroxypregnenolone
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional IUPAC Name2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry NumberNot Available
SMILES
CC12CC(O)C3C(CC=C4CC(O)CCC34C)C1CC[C@]2(O)C(=O)CO
InChI Identifier
InChI=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
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 20 Keto Steroid
  • 3 Hydroxy Steroid
  • Alpha Ketoaldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
  • Tertiary Alcohol
Direct ParentGluco/mineralocorticoids, Progestogins and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area97.99ChemAxon
rotatable bond count2ChemAxon
refractivity98.45ChemAxon
polarizability40.06ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130map00140
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024064
KNApSAcK IDNot Available
Chemspider ID389583
KEGG Compound IDC05489
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06760
Metagene LinkHMDB06760
METLIN IDNot Available
PubChem Compound440708
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
CYP11B1
Uniprot ID:
P15538
Reactions
17a,21-Dihydroxypreg-nenolone + Reduced ferredoxin + Oxygen unknown 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Waterdetails
Gene Name:
HSD3B1
Uniprot ID:
P14060
Reactions
Hydrocortisone + Hydrogen Ion + NADH unknown 11b,17a,21-Trihydroxypreg-nenolone + NADdetails
Gene Name:
HSD3B2
Uniprot ID:
P26439
Reactions
Hydrocortisone + Hydrogen Ion + NADH unknown 11b,17a,21-Trihydroxypreg-nenolone + NADdetails
Gene Name:
CYP11B2
Uniprot ID:
P19099
Reactions
17a,21-Dihydroxypreg-nenolone + Reduced ferredoxin + Oxygen unknown 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Waterdetails