Glucosyl (2E,6E,10x)-10,11-dihydroxy-2,6-farnesadienoate (CHEM031253)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:30:51 UTC
Update Date2016-11-09 01:19:14 UTC
Accession NumberCHEM031253
Identification
Common NameGlucosyl (2E,6E,10x)-10,11-dihydroxy-2,6-farnesadienoate
ClassSmall Molecule
DescriptionGlucosyl (2E,6E,10x)-10,11-dihydroxy-2,6-farnesadienoate is found in alcoholic beverages. Glucosyl (2E,6E,10x)-10,11-dihydroxy-2,6-farnesadienoate is present in Riesling wine.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Glucosyl (2E,6E,10X)-10,11-dihydroxy-2,6-farnesadienoic acidGenerator
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoic acidGenerator
Chemical FormulaC21H36O9
Average Molecular Mass432.505 g/mol
Monoisotopic Mass432.236 g/mol
CAS Registry Number204927-92-4
IUPAC Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoate
Traditional Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoate
SMILESC\C(CCC(O)C(C)(C)O)=C/CC\C(C)=C\C(=O)OC1OC(CO)C(O)C(O)C1O
InChI IdentifierInChI=1S/C21H36O9/c1-12(8-9-15(23)21(3,4)28)6-5-7-13(2)10-16(24)30-20-19(27)18(26)17(25)14(11-22)29-20/h6,10,14-15,17-20,22-23,25-28H,5,7-9,11H2,1-4H3/b12-6+,13-10+
InChI KeyMSRVZJWXQUEINS-WAAHFECUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Alkyl glycoside
  • Hexose monosaccharide
  • Fatty alcohol
  • Fatty acid ester
  • Fatty acyl
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility1.23 g/LALOGPS
logP0.45ALOGPS
logP0.31ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity109.63 m³·mol⁻¹ChemAxon
Polarizability46.83 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9403300000-89ade935c7e0b8ddf103Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-053r-6352239000-0602993cbc9044df41c3Spectrum
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, Positivesplash10-0wu0-0391300000-96cb8036abe15c5470c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ikc-0890000000-ac6016a0ea2b80c4e75eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gwr-4940000000-d898fe65205b8dedfd44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190200000-f109d4129463858c827cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j6r-3790100000-757dba12a668d21075ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frf-9360000000-f4c8435832b7ae591833Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-98eefd4e22763fd8648cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kuu-7394500000-9ad6af8b4a3d36af7234Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-7590000000-6fcd6402c3b69d270991Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0559800000-dc88cc13b9dd82292d9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1962000000-43abace242825e6dbcb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9700000000-0c360200b0b046d5784fSpectrum
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 IDHMDB0037823
FooDB IDFDB016968
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 ID167995
PubChem Compound ID131752240
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