21-Hydroxypregnenolone (CHEM021650)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:10 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021650
Identification
Common Name21-Hydroxypregnenolone
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass332.477 g/mol
Monoisotopic Mass332.235 g/mol
CAS Registry Number1164-98-3
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
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 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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
MSDSNot Available
General References
1. Daniewski, Andrzej Robert; Wojciechowska, Wanda. Preparation of 5-pregnene-3b, 21-diol-20-one. Pol. (1987), 4 pp.
2. Shackleton CH, Homoki J, Taylor NF: A paradox: elevated 21-hydroxypregnenolone production in newborns with 21-hydroxylase deficiency. Steroids. 1987 Apr-May;49(4-5):295-311.
3. Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)]. Biokhimiia. 1976 Sep;41(9):1619-27.
4. 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.
5. 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.
6. 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.
7. Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605.