Record Information
Version3.6
Creation Date2008-08-06 15:31:56 UTC
Update Date2013-02-09 00:15:16 UTC
HMDB IDHMDB06762
Secondary Accession NumbersNone
Metabolite Identification
Common Name17a,21-Dihydroxypreg-nenolone
Description17alpha,21-Dihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxypregnenolone is the 5th to last step in the synthesis of Cortol and is converted from 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.99.10). It is then converted to 11beta,17alpha,21-Trihydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.15.4).
Structure
Thumb
Synonyms
  1. 17alpha,21-Dihydroxypreg-nenolone
  2. 17alpha,21-Dihydroxypregnenolone
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one
Traditional IUPAC Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone
CAS Registry Number1167-48-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1
InChI KeyJNHJGXQUDOYJAK-IYRCEVNGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 17alpha-hydroxy steroid(ChEBI)
  • 21-hydroxy steroid(ChEBI)
  • 3beta-hydroxy steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
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 solubility0.057 g/LALOGPS
logP2.6ALOGPS
logP2.02ChemAxon
logS-3.8ALOGPS
pKa (strongest acidic)12.59ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity96.86ChemAxon
polarizability39.51ChemAxon
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 IDFDB024065
KNApSAcK IDNot Available
Chemspider ID167253
KEGG Compound IDC05487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06762
Metagene LinkHMDB06762
METLIN IDNot Available
PubChem Compound192735
PDB IDNot Available
ChEBI ID27832
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
Cortexolone + Hydrogen Ion + NADH unknown 17a,21-Dihydroxypreg-nenolone + NADdetails
Gene Name:
HSD3B2
Uniprot ID:
P26439
Reactions
Cortexolone + Hydrogen Ion + NADH unknown 17a,21-Dihydroxypreg-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
Gene Name:
P450-CYP21B
Uniprot ID:
Q16874
Gene Name:
CYP21A2
Uniprot ID:
P08686
Reactions
17a-Hydroxypregnenolone + NADPH + Hydrogen Ion + Oxygen unknown 17a,21-Dihydroxypreg-nenolone + NADP + Waterdetails