Showing metabocard for 21-Hydroxypregnenolone (BMDB0004026)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:16 UTC
Update Date2020-05-05 18:38:12 UTC
BMDB IDBMDB0004026
Secondary Accession Numbers
  • BMDB04026
Metabolite Identification
Common Name21-Hydroxypregnenolone
Description21-Hydroxypregnenolone, also known as 21-hydroxypregnenolone, 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. Thus, 21-hydroxypregnenolone is considered to be a steroid lipid molecule. 21-Hydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 21-Hydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 21-Hydroxypregnenolone can be converted into deoxycorticosterone through the action of the enzyme 3-beta-HSD 1. In addition, 21-Hydroxypregnenolone can be biosynthesized from pregnenolone through its interaction with the enzyme steroid 21-hydroxylase. In cattle, 21-hydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
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
Traditional Name21-hydroxypregnenolone
CAS Registry Number1164-98-3
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
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected 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
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-004u-4910000000-a498e59adb4a11849d3eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-4910000000-a498e59adb4a11849d3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0196000000-9576ba4a3e3fe81eccd0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-1014900000-72c174690c4421659ce6View 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0039000000-34e73b29188e789dcd9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0196000000-bd55e2f11df2c7f294d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2391000000-3937d95bf8b6f55a8382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9d13365707b48184b4b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-2069000000-284db8a88c06364a507eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3091000000-fbd05f20ca5983385f71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-5c433edd4be0c3ead061View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0795000000-5a50473d4855707105c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2940000000-422ddbc116e22dfcd136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-c4eb2a470a7bc24bb787View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0049000000-c8287b111bc120527734View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0092000000-cfcf5197be411a0f0d7eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Liver
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004026
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023281
KNApSAcK IDNot Available
Chemspider ID216208
KEGG Compound IDC05485
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link21-Hydroxypregnenolone
METLIN ID7002
PubChem Compound247020
PDB IDNot Available
ChEBI ID28043
References
Synthesis ReferenceDaniewski, Andrzej Robert; Wojciechowska, Wanda. Preparation of 5-pregnene-3b, 21-diol-20-one. Pol. (1987), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available