Showing metabocard for 16-a-Hydroxypregnenolone (BMDB0000315)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:27 UTC
Update Date2020-05-11 20:57:30 UTC
BMDB IDBMDB0000315
Secondary Accession Numbers
  • BMDB00315
Metabolite Identification
Common Name16-a-Hydroxypregnenolone
Description16-a-Hydroxypregnenolone 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. Thus, 16-a-hydroxypregnenolone is considered to be a steroid. Based on a literature review a significant number of articles have been published on 16-a-Hydroxypregnenolone.
Structure
Thumb
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0095000000-0ba118504e43c696fa6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0191000000-ab6b42b8427fc5af9393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2940000000-059af47f17d19474fb11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-624be9df633e48f47ffcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0091000000-a4889bb805ce3b259ef6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022i-0097000000-cef631450155e41ca7cfView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Umbilical Cord
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Umbilical CordExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000315
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
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 ReferencesNot Available