7-alpha-Hydroxy-4-Cholesten-3-one (CHEM021414)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 03:30:04 UTC
Update Date2016-10-28 10:04:17 UTC
Accession NumberCHEM021414
Identification
Common Name7-alpha-Hydroxy-4-Cholesten-3-one
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • Suspected Compounds - Waste Water
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha-Hydroxy-4-cholesten-3-oneChEBI
Cholest-4-en-7alpha-ol-3-oneChEBI
7a-Hydroxy-4-cholesten-3-oneGenerator
7Α-hydroxy-4-cholesten-3-oneGenerator
Cholest-4-en-7a-ol-3-oneGenerator
Cholest-4-en-7α-ol-3-oneGenerator
7 alpha-3Ox-CHMDB
7 alpha-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxycholest-4-en-3-oneHMDB
7-alpha-Hydroxy-4-cholesten-3-oneHMDB
7-alpha-Hydroxycholest-4-en-3-oneHMDB
7-Hydroxycholest-4-en-3-oneHMDB
7a-Hydroxy-4-cholesten-3-one-12alphaHMDB
7alpha-Hydroxycholest-4-en-3-oneHMDB
HCOHMDB
Cholest-4-en-7 alpha-ol-3-oneHMDB
7-Hydroxy-4-cholesten-3-oneHMDB
Chemical FormulaC27H44O2
Average Molecular Mass400.637 g/mol
Monoisotopic Mass400.334 g/mol
CAS Registry Number3862-25-7
IUPAC Name(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name7α-hydroxy-4-cholesten-3-one
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI IdentifierInChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyIOIZWEJGGCZDOL-RQDYSCIWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.00017 g/LALOGPS
logP5.46ALOGPS
logP6.37ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.16 m³·mol⁻¹ChemAxon
Polarizability50.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1339000000-8b87f8914863b4c7e8e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a6r-4672900000-f5cd21522bdf7607c5cbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019500000-764a74c3942ad452aa8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-3339100000-87e6e598932d57a6274eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-8469000000-b55e4f0de6f6dbfbe093Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b03a7cbfe5ca7374d51fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-903f15d46f6bf7449623Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1009000000-fd9c44e4f27a3c62b7e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-7ee7f5ca27c449403c35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvl-9246300000-d08ac46b391d42697238Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9620000000-e3dea04967eb9e6421c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-dc23ba87137530d83f68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dc23ba87137530d83f68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-75e53e521203e582561bSpectrum
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 IDHMDB0001993
FooDB IDFDB022786
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45848
BioCyc IDNot Available
METLIN ID6419
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110306
ChEBI ID17899
PubChem Compound ID123743
Kegg Compound IDC05455
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Alexander, David L.; Fisher, Jed F. A convenient synthesis of 7a-hydroxycholest-4-en-3-one by the hydroxypropyl-b-cyclodextrin-facilitated cholesterol oxidase oxidation of 3b,7a-cholest-5-ene-3,7-diol. Steroids (1995), 60(3), 290-4.
2. Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55.
3. Lin RC, Fillenwarth MJ, Du X: Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Hepatology. 1998 Jan;27(1):100-7.
4. Axelson M, Bjorkhem I, Reihner E, Einarsson K: The plasma level of 7 alpha-hydroxy-4-cholesten-3-one reflects the activity of hepatic cholesterol 7 alpha-hydroxylase in man. FEBS Lett. 1991 Jun 24;284(2):216-8.
5. Skrede S, Bjorkhem I: A novel route for the biosynthesis of cholestanol, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. Scand J Clin Lab Invest Suppl. 1985;177:15-21.
6. Skrede S, Buchmann MS, Bjorkhem I: Hepatic 7 alpha-dehydroxylation of bile acid intermediates, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. J Lipid Res. 1988 Feb;29(2):157-64.
7. Sauter GH, Munzing W, von Ritter C, Paumgartner G: Bile acid malabsorption as a cause of chronic diarrhea: diagnostic value of 7alpha-hydroxy-4-cholesten-3-one in serum. Dig Dis Sci. 1999 Jan;44(1):14-9.
8. Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23.