(3alpha,20R,24Z)-3-Hydroxy-21-oxoeupha-8,24-dien-26-oic acid (CHEM027449)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:44:47 UTC
Update Date2016-11-09 01:18:27 UTC
Accession NumberCHEM027449
Identification
Common Name(3alpha,20R,24Z)-3-Hydroxy-21-oxoeupha-8,24-dien-26-oic acid
ClassSmall Molecule
Description3-Hydroxy-21-oxotirucalla-8,24-dien-26-oic acid is found in beverages. 3-Hydroxy-21-oxotirucalla-8,24-dien-26-oic acid is a constituent of Schinus molle (California peppertree).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3a,20R,24Z)-3-Hydroxy-21-oxoeupha-8,24-dien-26-OateGenerator
(3a,20R,24Z)-3-Hydroxy-21-oxoeupha-8,24-dien-26-Oic acidGenerator
(3alpha,20R,24Z)-3-Hydroxy-21-oxoeupha-8,24-dien-26-OateGenerator
(3Α,20R,24Z)-3-hydroxy-21-oxoeupha-8,24-dien-26-OateGenerator
(3Α,20R,24Z)-3-hydroxy-21-oxoeupha-8,24-dien-26-Oic acidGenerator
[6]-Gingerdiol 3,5-diacetic acidHMDB
(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-7-oxohept-2-enoateHMDB
Chemical FormulaC30H46O4
Average Molecular Mass470.684 g/mol
Monoisotopic Mass470.340 g/mol
CAS Registry Number195204-05-8
IUPAC Name(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-7-oxohept-2-enoic acid
Traditional Name(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-7-oxohept-2-enoic acid
SMILESC\C(=C\CCC(C=O)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3)C(O)=O
InChI IdentifierInChI=1S/C30H46O4/c1-19(26(33)34)8-7-9-20(18-31)21-12-16-30(6)23-10-11-24-27(2,3)25(32)14-15-28(24,4)22(23)13-17-29(21,30)5/h8,18,20-21,24-25,32H,7,9-17H2,1-6H3,(H,33,34)/b19-8-
InChI KeyVYZGQLBKGMFPIP-UWVJOHFNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 22-oxosteroid
  • 21-oxosteroid
  • Steroid acid
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • 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 Solubility0.0015 g/LALOGPS
logP6.07ALOGPS
logP5.68ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity137.03 m³·mol⁻¹ChemAxon
Polarizability56.01 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbc-0002900000-0d0a8a613545a9365298Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1001292000-31e344e489c9cd99fa89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-bda872e80325924440ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kds-1007900000-8c9cc5eabc98817cf7b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-3219600000-a65b0b39428129f7f92bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-44b2c5480ffbdd87e70aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lfr-0101900000-aa837e909391caf36aa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9415500000-1d0984c7fb6a4fe036ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-21d87b4be197e685b8abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0007900000-5a57cf5b66f6225b13bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-6109100000-92208dc1dc2af33580a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0104900000-87a25d2e7f79e1276728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02vi-1439200000-4a2f07e6ebb89ec841eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-9717000000-0b81db168fcd9fd6654eSpectrum
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 IDHMDB0033213
FooDB IDFDB011226
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4476431
ChEBI IDNot Available
PubChem Compound ID131751391
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