3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-oic acid (CHEM031437)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:39:11 UTC
Update Date2016-11-09 01:19:16 UTC
Accession NumberCHEM031437
Identification
Common Name3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-oic acid
ClassSmall Molecule
Description3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-oic acid is found in fruits. 3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-oic acid is a constituent of Eriobotrya japonica (loquat).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3a-O-trans-Feruloyl-2a-hydroxy-12-ursen-28-OateGenerator
3a-O-trans-Feruloyl-2a-hydroxy-12-ursen-28-Oic acidGenerator
3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-OateGenerator
3Α-O-trans-feruloyl-2α-hydroxy-12-ursen-28-OateGenerator
3Α-O-trans-feruloyl-2α-hydroxy-12-ursen-28-Oic acidGenerator
11-Hydroxy-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylateHMDB
Chemical FormulaC40H56O7
Average Molecular Mass648.868 g/mol
Monoisotopic Mass648.403 g/mol
CAS Registry Number351333-71-6
IUPAC Name11-hydroxy-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-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 Name11-hydroxy-10-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
SMILESCOC1=CC(\C=C\C(=O)OC2C(O)CC3(C)C(CCC4(C)C3CC=C3C5C(C)C(C)CCC5(CCC43C)C(O)=O)C2(C)C)=CC=C1O
InChI IdentifierInChI=1S/C40H56O7/c1-23-15-18-40(35(44)45)20-19-38(6)26(33(40)24(23)2)11-13-31-37(5)22-28(42)34(36(3,4)30(37)16-17-39(31,38)7)47-32(43)14-10-25-9-12-27(41)29(21-25)46-8/h9-12,14,21,23-24,28,30-31,33-34,41-42H,13,15-20,22H2,1-8H3,(H,44,45)/b14-10+
InChI KeyLOYUSEWSBJOCNL-GXDHUFHOSA-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
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic alcohol
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.0006 g/LALOGPS
logP7.3ALOGPS
logP8.08ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity183.07 m³·mol⁻¹ChemAxon
Polarizability74.61 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0032-0209605000-454f9d43a96cf67d4bf3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3alpha-O-trans-Feruloyl-2alpha-hydroxy-12-ursen-28-oic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0032-0400509000-79cb4e09cb3b388cbd48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0700915000-703ef359470c989c5398Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1302902000-4ea5c286b8f0555fed35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0300309000-e0085deb6b38f8c96813Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi9-0600924000-04fcb22c68f50bf64f54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0500900000-ed8e6df107f3a0eb2eb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100409000-bade8d90be00c5c2b4ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0912301000-e284c8cf70df109384e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-5931320000-3f6bbe1a7b5809e42d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000009000-b52ab98cb8bd6d9585aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmj-0900502000-fb6296c08c32f991688cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-0900213000-744c92d9e6c9677e11f6Spectrum
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 IDHMDB0038021
FooDB IDFDB017230
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014499
ChEBI IDNot Available
PubChem Compound ID131752276
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