11beta,17alpha,21-Trihydroxypreg-nenolone (CHEM036228)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:19:53 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036228
Identification
Common Name11beta,17alpha,21-Trihydroxypreg-nenolone
ClassSmall Molecule
Description11b,17a,21-Trihydroxypreg-nenolone 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. 11b,17a,21-Trihydroxypreg-nenolone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 11b,17a,21-Trihydroxypreg-nenolone participates in a number of enzymatic reactions, within cattle. In particular, 11b,17a,21-Trihydroxypreg-nenolone can be biosynthesized from 17alpha,21-dihydroxypregnenolone through its interaction with the enzyme cytochrome P450 11B1. In addition, 11b,17a,21-Trihydroxypreg-nenolone and NAD can be biosynthesized from cortisol, nadh, and hydrogen ion; which is catalyzed by the enzyme 3 beta-hydroxysteroid dehydrogenase/delta 5-->4-isomerase type 2. In cattle, 11b,17a,21-trihydroxypreg-nenolone is involved in the metabolic pathway called the steroidogenesis pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11beta,17alpha,21-Trihydroxypreg-nenoloneHMDB
11beta,17alpha,21-TrihydroxypregnenoloneHMDB
Chemical FormulaC21H32O5
Average Molecular Mass364.476 g/mol
Monoisotopic Mass364.225 g/mol
CAS Registry NumberNot Available
IUPAC Name2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
Traditional Name2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethanone
SMILESCC12CC(O)C3C(CC=C4CC(O)CCC34C)C1CC[C@]2(O)C(=O)CO
InChI IdentifierInChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h3,13-16,18,22-24,26H,4-11H2,1-2H3/t13?,14?,15?,16?,18?,19?,20?,21-/m0/s1
InChI KeyHAFVWTUQBYRPOB-QGGNSXJXSA-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
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.54 g/LALOGPS
logP1.38ALOGPS
logP0.71ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.45 m³·mol⁻¹ChemAxon
Polarizability40.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0541-3359000000-db5da057c94c2a047b10Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000i-1010239000-01d0907903079ebb80e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-d6f315e61bbd67eae72aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0059000000-80e727e264ca8a26a2b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0292000000-3aa262e1ed45e0e16207Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-c6648ee147e3babd9fc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btj-2029000000-37d8ba5fa07061ac854aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9087000000-1ebec2db5084d047ee8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016s-0009000000-6ce3ed6f29dccbfe6478Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1926000000-f119874166aedccc6ac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-5791000000-559a7f43ae2c76413fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0009000000-67b158b5ac05ed2344abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-067i-5019000000-a9c81ea29263a6d18742Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-2098000000-67c584ed2fd965c412d9Spectrum
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 IDHMDB0006760
FooDB IDFDB024064
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389583
ChEBI IDNot Available
PubChem Compound ID440708
Kegg Compound IDC05489
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available