(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one (CHEM032772)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:41:22 UTC
Update Date2016-11-09 01:20:47 UTC
Accession NumberCHEM032772
Identification
Common Name(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one
ClassSmall Molecule
DescriptionConstituent of the immature seeds of Phaseolus vulgaris (kidney bean). (2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one is found in many foods, some of which are pulses, yellow wax bean, common bean, and green bean.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2a,3a,5a,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-oneGenerator
(2Α,3α,5α,22R,23R)-2,3,22,23-tetrahydroxy-25-methylergost-24(28)en-6-oneGenerator
25-MethyldiolichosteroneHMDB
25-MethyldolichosteroneHMDB
Chemical FormulaC29H48O5
Average Molecular Mass476.688 g/mol
Monoisotopic Mass476.350 g/mol
CAS Registry Number111618-87-2
IUPAC Name14-(3,4-dihydroxy-6,6-dimethyl-5-methylideneheptan-2-yl)-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one
Traditional Name14-(3,4-dihydroxy-6,6-dimethyl-5-methylideneheptan-2-yl)-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one
SMILESCC(C(O)C(O)C(=C)C(C)(C)C)C1CCC2C3CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI IdentifierInChI=1S/C29H48O5/c1-15(25(33)26(34)16(2)27(3,4)5)18-8-9-19-17-12-22(30)21-13-23(31)24(32)14-29(21,7)20(17)10-11-28(18,19)6/h15,17-21,23-26,31-34H,2,8-14H2,1,3-7H3
InChI KeyHAOQPQZVDMAOKT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • Ecdysteroid
  • 23-hydroxysteroid
  • 22-hydroxysteroid
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 6-oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.024 g/LALOGPS
logP3.05ALOGPS
logP3.53ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity133.4 m³·mol⁻¹ChemAxon
Polarizability55.53 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1507900000-897e16ccbea7ecb07da8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-2210029000-30690aab9742d3c68536Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vi-0102900000-2fd81e8b2a091a103605Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4908600000-5884bd376a7478af5388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4903000000-6cf175c82182fbb9e7b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-60025f5dbcc3fecbecbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9208700000-89a36f122832868194d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9104000000-b96e458fdd73a3345812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ur-1019400000-6c5a3de93160cfe40425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07w9-1019100000-104c888a3346d4106002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9501000000-950dac189be4f90068b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-86a4f613459c2b1bffaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1105900000-992b4544e6eac49e2a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009400000-ad283d56f2ffd21611a1Spectrum
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 IDHMDB0039443
FooDB IDFDB019040
Phenol Explorer IDNot Available
KNApSAcK IDC00000196
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID13991214
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. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM