Cichorioside L (CHEM024035)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:26:58 UTC
Update Date2016-11-09 01:17:49 UTC
Accession NumberCHEM024035
Identification
Common NameCichorioside L
ClassSmall Molecule
DescriptionCichorioside l is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cichorioside l can be found in endive, which makes cichorioside l a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC26H40O13
Average Molecular Mass560.588 g/mol
Monoisotopic Mass560.247 g/mol
CAS Registry Number1086489-90-8
IUPAC Name(3S,3aR,4S,9S,11aR)-4-{[(2R,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-hydroxy-3,6,10-trimethyl-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
Traditional Name(3S,3aR,4S,9S,11aR)-4-{[(2R,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-hydroxy-3,6,10-trimethyl-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
SMILES[H][C@]12OC(=O)[C@@H](C)[C@]1([H])[C@H](C\C(C)=C/C[C@H](O)C(C)=C2)O[C@]1([H])O[C@H](CO[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C26H40O13/c1-11-4-5-14(28)12(2)7-16-18(13(3)23(33)37-16)15(6-11)38-24-21(31)20(30)19(29)17(39-24)8-35-25-22(32)26(34,9-27)10-36-25/h4,7,13-22,24-25,27-32,34H,5-6,8-10H2,1-3H3/b11-4-,12-7-/t13-,14-,15-,16+,17+,18+,19+,20-,21+,22-,24+,25+,26+/m0/s1
InChI KeyNFLQLYZLVYTURD-YSEMMFJCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Terpene glycoside
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Gamma butyrolactone
  • Oxane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • 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 Solubility4.91 g/LALOGPS
logP-0.96ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area204.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132.31 m³·mol⁻¹ChemAxon
Polarizability56.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02td-0190270000-5a63276c73a627de5d54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0490110000-e338636f0180c6fd6c28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2590000000-caaf3dfc6e18a8776b77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ot-0360190000-eec4c3061079d0c17439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0590030000-5f2d279e0d5ab6a242a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-1290000000-2dd8addfdb09207038beSpectrum
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 IDNot Available
FooDB IDFDB001804
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 IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available