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Showing Compound 16-alpha-Hydroxypregnenolone (FDB021942)

Record Information
Version1.0
Creation date2011-09-21 00:05:35 UTC
Update date2015-07-21 06:56:54 UTC
Primary IDFDB021942
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16-alpha-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.
CAS Number520-88-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(3β,16α)-3,16-dihydroxypregn-5-en-20-oneGenerator
16-α-hydroxypregnenoloneGenerator
16α-hydroxypregnenoloneGenerator
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
Chemical FormulaC21H32O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS16-alpha-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-010d-1094000000-48d07553e41a7f133af6Spectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2016900000-9dfed36ce29372d939deSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16-alpha-Hydroxypregnenolone, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0049000000-2ccfec5d85aa1a19cec32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0194000000-e0041edd20068fee3d7b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6v-1391000000-a896ab547c468e369ce52015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-2ab7fa56b70d72f5890d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0029000000-8ccb6ff65b91e81bbea52015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ri-1093000000-56249f185b497261aed42015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0095000000-0ba118504e43c696fa6d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0191000000-ab6b42b8427fc5af93932021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2940000000-059af47f17d19474fb112021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-624be9df633e48f47ffc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0091000000-a4889bb805ce3b259ef62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022i-0097000000-cef631450155e41ca7cf2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID4955002
ChEMBL IDCHEMBL1908004
KEGG Compound IDC06390
Pubchem Compound ID6452574
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00315
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference