7alpha,24-Dihydroxy-4-cholesten-3-one (CHEM040899)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:04:02 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040899
Identification
Common Name7alpha,24-Dihydroxy-4-cholesten-3-one
ClassSmall Molecule
Description7 alpha,24-Dihydroxy-4-cholesten-3-one is involved in the primary bile acid biosynthesis pathway. 7 alpha,24-Dihydroxy-4-cholesten-3-one is produced from (24S)-Cholest-5-ene-3 beta,7 alpha,24-triol through the action of HSD3B7 (EC:1.1.1.181).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7 a,24-Dihydroxy-4-cholesten-3-oneGenerator
7 Α,24-dihydroxy-4-cholesten-3-oneGenerator
Phosphatidylcholine(20:2/18:1)HMDB
GPCho(20:2/18:1)HMDB
Phosphatidylcholine(38:3)HMDB
PC(38:3)HMDB
LecithinHMDB
GPCho(38:3)HMDB
1-Eicosadienoyl-2-vaccenoyl-sn-glycero-3-phosphocholineHMDB
1-(11Z,14Z-Eicosadienoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholineHMDB
PC(20:2/18:1)HMDB
Chemical FormulaC27H44O3
Average Molecular Mass416.637 g/mol
Monoisotopic Mass416.329 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R,9R,15R)-9-hydroxy-14-[(2R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,9R,15R)-9-hydroxy-14-[(2R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILESCC(C)C(O)CC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
InChI IdentifierInChI=1S/C27H44O3/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h14,16-17,20-25,29-30H,6-13,15H2,1-5H3/t17-,20?,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyLFFHZNXDGBQZCO-PXNWSTMDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • 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 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 Solubility0.0044 g/LALOGPS
logP4.25ALOGPS
logP5.06ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.75 m³·mol⁻¹ChemAxon
Polarizability50.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udv-2349200000-88b917be981a76eec917Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1323090000-48b8d785016e805d5d43Spectrum
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, Positivesplash10-00kb-0009200000-4cf75e191b124774d2adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-3109100000-c6286fa0dc6f3f0ea5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-076r-4129000000-9bec2ca68ef0c19288dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-1b4a764d3fd2c8b8c754Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009600000-a0c11967d82e82fe7958Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0072-6009000000-4634671937f1356686f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d929Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3002900000-107ba51f9809f31a908aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016s-0009100000-34c1ffcee09c9d904e1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0109100000-77e7030570bcde433b6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2529000000-e5fd83382ae007b146d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-6972000000-188ee8775bbd4dac7ca2Spectrum
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 IDHMDB0012457
FooDB IDFDB029073
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID89082
PubChem Compound ID53481410
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM