Showing metabocard for 21-Hydroxypregnenolone (LMDB00443)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:49:58 UTC
Update Date2016-09-23 18:45:28 UTC
LmdbLMDB00443
Secondary Accession NumbersNone
Metabolite Identification
Common 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 animal adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in animal. (PMID 974176 , 3347051 , 3495701 , 7382480 , 6247575 ).
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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 KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-004u-4910000000-a498e59adb4a11849d3eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-4910000000-a498e59adb4a11849d3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0196000000-9576ba4a3e3fe81eccd0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-1014900000-72c174690c4421659ce6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0039000000-34e73b29188e789dcd9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0196000000-bd55e2f11df2c7f294d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2391000000-3937d95bf8b6f55a8382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9d13365707b48184b4b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-2069000000-284db8a88c06364a507eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3091000000-fbd05f20ca5983385f71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-5c433edd4be0c3ead061Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0795000000-5a50473d4855707105c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2940000000-422ddbc116e22dfcd136Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-c4eb2a470a7bc24bb787Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0049000000-c8287b111bc120527734Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0092000000-cfcf5197be411a0f0d7eSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0004026
FooDB IDFDB023281
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7002
PDB IDNot Available
Wikipedia Link21-Hydroxypregnenolone
Chemspider ID216208
ChEBI ID28043
PubChem Compound ID247020
Kegg Compound IDC05485
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)]. Biokhimiia. 1976 Sep;41(9):1619-27. [974176 ]
  2. Guerami A, Varner MW, Shackleton CH, MacDonald PC, Casey ML: Origin of deoxycorticosterone and deoxycorticosterone sulfate in human pregnancy: absence of steroid 21-sulfatase activity in sulfatase-deficient placenta. J Steroid Biochem. 1988 Jan;29(1):57-62. [3347051 ]
  3. Dehennin L, Nahoul K, Scholler R: Steroid 21-hydroxylation by human preovulatory follicles from stimulated cycles: a mass spectrometrical study of deoxycorticosterone, 21-hydroxypregnenolone and 11-deoxycortisol in follicular fluid. J Steroid Biochem. 1987 Mar;26(3):337-43. [3495701 ]
  4. Kaufmann SH, Sinterhauf K, Lommer D: 21-Hydroxylation of pregnenolone by microsomal preparations of rat and human adrenals. J Steroid Biochem. 1980 Jan;13(1):101-3. [7382480 ]
  5. Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [6247575 ]