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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-11-06 18:48:53 UTC
HMDB IDHMDB0000315
Secondary Accession Numbers
  • HMDB00315
Metabolite Identification
Common Name16-a-Hydroxypregnenolone
Description16-alpha-hydroxypregnenolone, also known as (3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one, is classified as a gluco/mineralocorticoid, a progestogin or aprogestogin derivative. Gluco/mineralocorticoids are steroids with a structure based on a hydroxylated prostane moiety. Thus, 16-alpha-hydroxypregnenolone is a steroid lipid molecule. 16-alpha-hydroxypregnenolone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-alpha-hydroxypregnenolone can be found primarily in blood, urine and in human umbilical cord tissue. Within the cell, 16-alpha-hydroxypregnenolone is primarily located in the membrane, and in the nucleus bound to cytoplasmic glucocorticoid receptors. 16-alpha-hydroxypregnenolone exists in all vertebrates. 16-a-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency (PMID 6980322 ).
Structure
Thumb
Synonyms
ValueSource
(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-oneChEBI
16-alpha-HydroxypregnenoloneChEBI
(3b,16a)-3,16-Dihydroxypregn-5-en-20-oneGenerator
(3β,16α)-3,16-dihydroxypregn-5-en-20-oneGenerator
16-α-hydroxypregnenoloneGenerator
16 alpha-HydroxypregnenoloneHMDB
16-a-Hydroxy-pregnenoloneHMDB
16-alpha-Hydroxy-pregnenoloneHMDB
16alpha-HydroxypregnenoloneHMDB
3b,16a-Dihydroxypreg-5-en-20-oneHMDB
3b,16a-Dihydroxypregn-5-en-20-oneHMDB
3b,16a-Dihydroxypregnen-5-en-20-oneHMDB
5-Pregnene-3b,16a-diol-20-oneHMDB
Pregn-5-en-3b,16a-diol-20-oneHMDB
3 alpha,16 alpha-Dihydroxypregn-5-en-20-oneMeSH
3 beta,16 alpha-Dihydroxypregn-5-en-20-oneMeSH
3 beta,16 beta-Dihydroxypregn-5-en-20-oneMeSH
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
Traditional Name16α-hydroxypregnenolone
CAS Registry Number520-88-7
SMILES
[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1
InChI KeyZAKJZPQDUPCXSD-YRWKUUEZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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
logP2.79ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.27 m³·mol⁻¹ChemAxon
Polarizability38.91 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-010d-1094000000-48d07553e41a7f133af6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2016900000-9dfed36ce29372d939deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0049000000-2ccfec5d85aa1a19cec3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0194000000-e0041edd20068fee3d7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6v-1391000000-a896ab547c468e369ce5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-2ab7fa56b70d72f5890dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0029000000-8ccb6ff65b91e81bbea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ri-1093000000-56249f185b497261aed4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Umbilical cord
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.1 +/- 2.3 uMNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.05 (0.0 - 0.1) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Newborn (0-30 days old)Not Available
Congenital adrenal hyperplasia
details
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 IDFDB021942
KNApSAcK IDNot Available
Chemspider ID4955002
KEGG Compound IDC06390
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5304
PubChem Compound6452574
PDB IDNot Available
ChEBI ID771
References
Synthesis ReferencePierrepoint, C. G.; Griffiths, Keith; Grant, James K. In vitro studies of feminizing tumors of the testis of man and dog. Proc. Int. Congr. Horm. Steroids, 2nd (1967), Meeting Date 1966, 761-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
  2. Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]