Record Information
Version1.0
Creation date2011-09-21 00:27:25 UTC
Update date2015-07-21 06:57:37 UTC
Primary IDFDB023281
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name21-Hydroxypregnenolone
Description21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575) [HMDB]
CAS Number1164-98-3
Structure
Thumb
Synonyms
SynonymSource
(3beta)-3,21-Dihydroxypregn-5-en-20-oneChEBI
(3b)-3,21-Dihydroxypregn-5-en-20-oneGenerator
(3Β)-3,21-dihydroxypregn-5-en-20-oneGenerator
(3b)-3,21-Dihydroxy-pregn-5-en-20-oneHMDB
3b,21-Dihydroxy-5-pregnen-20-oneHMDB
3b,21-Dihydroxy-pregn-5-en-20-oneHMDB
5-Pregnen-3.beta.,21-diol-20-oneHMDB
5-Pregnen-3b,21-diol-20-oneHMDB
5-Pregnen-3beta,21-diol-20-oneHMDB
Oprea1_642453HMDB
Pregn-5-ene-3b,21-diol-20-oneHMDB
(3b)-3,21-dihydroxy-Pregn-5-en-20-onehmdb
(3β)-3,21-dihydroxypregn-5-en-20-oneGenerator
21-hydroxypregnenolonehmdb
3b,21-dihydroxy-Pregn-5-en-20-onehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.22ALOGPS
logP2.76ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.46 m³·mol⁻¹ChemAxon
Polarizability38.84 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H32O3
IUPAC name2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
InChI IdentifierInChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1
InChI KeyMOIQRAOBRXUWGN-WPWXJNKXSA-N
Isomeric SMILES[H][C@@]12CC[C@H](C(=O)CO)[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 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Delta-5-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 - Experimental
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-004u-4910000000-a498e59adb4a11849d3eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-4910000000-a498e59adb4a11849d3eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0196000000-9576ba4a3e3fe81eccd0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-1014900000-72c174690c4421659ce6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0039000000-34e73b29188e789dcd9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0196000000-bd55e2f11df2c7f294d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2391000000-3937d95bf8b6f55a8382JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9d13365707b48184b4b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-2069000000-284db8a88c06364a507eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3091000000-fbd05f20ca5983385f71JSpectraViewer
ChemSpider ID216208
ChEMBL IDCHEMBL1908012
KEGG Compound IDC05485
Pubchem Compound ID247020
Pubchem Substance IDNot Available
ChEBI ID28043
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04026
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
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 21, subfamily A, polypeptide 2CYP21A2Q08AG9
Cytochrome P450 21-hydroxylaseP450-CYP21BQ16874
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference