(1beta,2alpha,3alpha)-1,2,3,24-Tetrahydroxy-12-oleanen-28-oic acid (CHEM029387)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:08:13 UTC
Update Date2016-11-09 01:18:52 UTC
Accession NumberCHEM029387
Identification
Common Name(1beta,2alpha,3alpha)-1,2,3,24-Tetrahydroxy-12-oleanen-28-oic acid
ClassSmall Molecule
Description(1beta,2alpha,3alpha)-1,2,3,24-Tetrahydroxy-12-oleanen-28-oic acid is found in citrus. (1beta,2alpha,3alpha)-1,2,3,24-Tetrahydroxy-12-oleanen-28-oic acid is a constituent of nectarine fruits (Prunus persica cv. Fantasia)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1b,2a,3a)-1,2,3,24-Tetrahydroxy-12-oleanen-28-OateGenerator
(1b,2a,3a)-1,2,3,24-Tetrahydroxy-12-oleanen-28-Oic acidGenerator
(1beta,2alpha,3alpha)-1,2,3,24-Tetrahydroxy-12-oleanen-28-OateGenerator
(1Β,2α,3α)-1,2,3,24-tetrahydroxy-12-oleanen-28-OateGenerator
(1Β,2α,3α)-1,2,3,24-tetrahydroxy-12-oleanen-28-Oic acidGenerator
10,11,12-Trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylateHMDB
Chemical FormulaC30H48O6
Average Molecular Mass504.699 g/mol
Monoisotopic Mass504.345 g/mol
CAS Registry Number254098-66-3
IUPAC Name10,11,12-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
Traditional Name10,11,12-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILESCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)C(O)C(O)C(O)C(C)(CO)C5CCC34C)C2C1)C(O)=O
InChI IdentifierInChI=1S/C30H48O6/c1-25(2)11-13-30(24(35)36)14-12-27(4)17(18(30)15-25)7-8-20-28(27,5)10-9-19-26(3,16-31)22(33)21(32)23(34)29(19,20)6/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)
InChI KeyYOGUTEYZFFDORB-UHFFFAOYSA-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
  • 12-hydroxysteroid
  • 11-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • 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 Solubility0.033 g/LALOGPS
logP4.11ALOGPS
logP3.32ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity137.97 m³·mol⁻¹ChemAxon
Polarizability57.42 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-007c-0002900000-919807a8cd207369055bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2001169000-fae31a2c49613de8054cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0000920000-376508baf87c5c3dec15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-0000900000-321800376e8534f2d5adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-2114900000-999f9c24dbc73736ee48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000960000-9aeae5b77ee25802a2c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pkl-0000910000-b17c969367f2e8c22cd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-1001900000-2362326be2e1b52d33d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000690000-47118fd32c7c1dd044edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0011930000-b3f69e09ac045dc384c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1922000000-47860975a78b47984531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-5e15ec7ab6ea3bad2c07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000980000-054f25a1078a46ae31bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-3000930000-2e0b39d50b0415c30995Spectrum
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 IDHMDB0035487
FooDB IDFDB014173
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013935
ChEBI ID169308
PubChem Compound ID131751780
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