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Showing Compound Cichorioside I (FDB001801)

Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001801
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCichorioside I
Description(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione 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. Based on a literature review very few articles have been published on (3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione.
CAS Number1086489-81-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility11.1 g/LALOGPS
logP-0.96ALOGPS
logP-1.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.48 m³·mol⁻¹ChemAxon
Polarizability44.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H28O10
IUPAC name(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione
InChI IdentifierInChI=1S/C21H28O10/c1-7-3-11-14(8(2)20(28)30-11)17(25)15-9(4-10(23)13(7)15)6-29-21-19(27)18(26)16(24)12(5-22)31-21/h4,8,11-12,14-19,21-22,24-27H,3,5-6H2,1-2H3/t8-,11-,12?,14+,15-,16?,17-,18?,19?,21?/m0/s1
InChI KeyPOOPERNNBMZLBU-YFVSWLSASA-N
Isomeric SMILES[H][C@]12CC(C)=C3C(=O)C=C(COC4OC(CO)C(O)C(O)C4O)[C@]3([H])[C@@H](O)[C@]1([H])[C@H](C)C(=O)O2
Average Molecular Weight440.441
Monoisotopic Molecular Weight440.168247116
Classification
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
  • Helenalin-skeleton
  • Terpene glycoside
  • Terpene lactone
  • Sesquiterpenoid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Gamma butyrolactone
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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, Positivesplash10-01vo-0161900000-e3bf8faea4f71a9b467f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0591200000-7eac3948eba8468f09552016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-4982100000-1b7d54e556dcc57aeaf02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1233900000-a91118325b91e148dfc32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-076r-4943500000-3be2edd28134666e67ee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0203-9470000000-d396724bd706dbabf9062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0010900000-a13ab6425e9509aa04fb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02kc-0469800000-5820d5a8c34a7c9c8a932021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3296000000-ae0722955307d4f34d1d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-59322d265919df5c7bf42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05w0-9086700000-8f4626f0f9eb5df926772021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9161300000-fc015083edddbecfd5202021-10-21View 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 IDC00029955
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.