Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001796
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCichorioside C
DescriptionCichorioside C 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 C is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number117013-50-0
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility3.74 g/LALOGPS
logP-0.52ALOGPS
logP-0.67ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.64 m³·mol⁻¹ChemAxon
Polarizability43.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O9
IUPAC name4-hydroxy-3,6,10-trimethyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
InChI IdentifierInChI=1S/C21H32O9/c1-9-4-5-13(29-21-19(26)18(25)17(24)15(8-22)30-21)10(2)7-14-16(12(23)6-9)11(3)20(27)28-14/h4,7,11-19,21-26H,5-6,8H2,1-3H3/b9-4-,10-7-
InChI KeyJSOWYWSOJSNXRV-APXACOEDSA-N
Isomeric SMILESCC1C2C(OC1=O)C=C(C)C(C\C=C(C)/CC2O)OC1OC(CO)C(O)C(O)C1O
Average Molecular Weight428.4734
Monoisotopic Molecular Weight428.204632622
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
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Gamma butyrolactone
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02bb-0191500000-d33a94d2ed70c7627b95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0591000000-b49a00a51045782d05e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-4490000000-633ef65d44719f0d15b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1283900000-68e5a21607c6ed914abbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1191100000-5513937d46072450e768Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-2090000000-fdce83e36e3c771e5433Spectrum
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 IDCICHORIOSIDE-C
BIGG IDNot Available
KNApSAcK IDC00029950
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
FoodReference
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).