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Showing metabocard for 16-a-Hydroxypregnenolone (HMDB0000315)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:03 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
Data?1582752123
MOLSDFPDBSMILESInChI
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-oneHMDB
3 beta,16 alpha-Dihydroxypregn-5-en-20-oneHMDB
3 beta,16 beta-Dihydroxypregn-5-en-20-oneHMDB
16a-HydroxypregnenoloneHMDB
16Α-hydroxypregnenoloneHMDB
16-a-HydroxypregnenoloneGenerator
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[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
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
Description 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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Polarizability38.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-010d-1094000000-48d07553e41a7f133af6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2016900000-9dfed36ce29372d939deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0049000000-2ccfec5d85aa1a19cec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0194000000-e0041edd20068fee3d7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6v-1391000000-a896ab547c468e369ce5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-2ab7fa56b70d72f5890dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0029000000-8ccb6ff65b91e81bbea5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ri-1093000000-56249f185b497261aed4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Umbilical cord
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Available
Congenital adrenal hyperplasia		 details
Associated Disorders and Diseases
Disease References
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
  1. 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 ]
Associated OMIM IDs
  • 201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]