11,13-Dihydrotaraxinic acid glucosyl ester (CHEM029738)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:22:44 UTC
Update Date2016-11-09 01:18:56 UTC
Accession NumberCHEM029738
Identification
Common Name11,13-Dihydrotaraxinic acid glucosyl ester
ClassSmall Molecule
Description11,13-Dihydrotaraxinic acid glucosyl ester is found in alcoholic beverages. 11,13-Dihydrotaraxinic acid glucosyl ester is a constituent of Taraxacum officinale (dandelion)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11,13-Dihydrotaraxinate glucosyl esterGenerator
(2R,3R,4S,5R,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)oxan-4-yl (3as,11as)-3,10-dimethyl-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acidHMDB
Chemical FormulaC21H30O9
Average Molecular Mass426.458 g/mol
Monoisotopic Mass426.189 g/mol
CAS Registry Number75911-16-9
IUPAC Name(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate
Traditional Name(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate
SMILESCC1[C@@H]2CCC(=CCC\C(C)=C\[C@H]2OC1=O)C(=O)O[C@@H]1[C@@H](O)[C@H](O)O[C@H](CO)[C@H]1O
InChI IdentifierInChI=1S/C21H30O9/c1-10-4-3-5-12(6-7-13-11(2)19(25)28-14(13)8-10)20(26)30-18-16(23)15(9-22)29-21(27)17(18)24/h5,8,11,13-18,21-24,27H,3-4,6-7,9H2,1-2H3/b10-8+,12-5+/t11?,13-,14+,15+,16+,17+,18-,21+/m0/s1
InChI KeyGHCVBVCIPFPICQ-RYCRGVOFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSaccharolipids
Sub ClassNot Available
Direct ParentSaccharolipids
Alternative Parents
Substituents
  • Saccharolipid
  • Germacranolide
  • Terpene lactone
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Hexose monosaccharide
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Monosaccharide
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility2.56 g/LALOGPS
logP0.26ALOGPS
logP0.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.29 m³·mol⁻¹ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-114i-9217100000-05aa56849ff19b39913bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fai-6251092000-2dd145701a61322d633eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0334900000-dfc967b42bede4c455b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vv-3759500000-f7750ce9c57d113f4ad5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4932000000-c7cc30704d428447bab3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1128900000-e8259516ec66c68c638fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-4396400000-4fbe951a9785801eb58bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-4190000000-968b5316f343230c6df7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7j-0049700000-e0a9248d116b3892d4ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-1295000000-8bb72cc26d35360b531dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2490000000-b8f6654bcae77069823aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0023900000-32ff7bbd4c1fcd12b9dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-11w9-8946000000-3832b587ec5e57553845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9152000000-535a328bced96f167505Spectrum
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 IDHMDB0035867
FooDB IDFDB014647
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777145
ChEBI ID168344
PubChem Compound ID131751877
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kisiel W, Barszcz B: Further sesquiterpenoids and phenolics from Taraxacum officinale. Fitoterapia. 2000 Jun;71(3):269-73.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
3. Hansel, R., Kartarahardja, M., Huang, J. T., Bohlmann, F., Sesquiterpenlacton-beta-D-glucospyranoside sowie ein neues Eudesmanolid aus Taraxacum officinale, Phytochemistry, 1980, 19, 857-861 [Isolation]