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Showing Compound Cichorioside L (FDB001804)

Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001804
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCichorioside L
DescriptionCichorioside L 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. Cichorioside L is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number1086489-90-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H40O13
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
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
Isomeric 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
Average Molecular Weight560.588
Monoisotopic Molecular Weight560.246891366
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02td-0190270000-5a63276c73a627de5d542016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0490110000-e338636f0180c6fd6c282016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2590000000-caaf3dfc6e18a8776b772016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ot-0360190000-eec4c3061079d0c174392016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0590030000-5f2d279e0d5ab6a242a72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-1290000000-2dd8addfdb09207038be2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00029958
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
EndiveExpected but not quantifiedNot AvailableKNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.