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Showing Compound Cichoriin (FDB002777)

Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002777
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCichoriin
DescriptionCichoriin belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Cichoriin is found, on average, in the highest concentration within chicories (Cichorium intybus). Cichoriin has also been detected, but not quantified in, green vegetables. This could make cichoriin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cichoriin.
CAS Number531-58-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
6-HydroxyskimminHMDB
CichoriosideHMDB
Cichoriindb_source
Predicted Properties
PropertyValueSource
Water Solubility10.8 g/LALOGPS
logP-0.54ALOGPS
logP-1.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.65 m³·mol⁻¹ChemAxon
Polarizability31.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H16O9
IUPAC name6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
InChI IdentifierInChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-4-8-6(3-7(9)17)1-2-11(18)22-8/h1-4,10,12-17,19-21H,5H2
InChI KeyWNBCMONIPIJTSB-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O
Average Molecular Weight340.2821
Monoisotopic Molecular Weight340.07943211
Classification
Description Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassCoumarin glycosides
Direct ParentCoumarin glycosides
Alternative Parents
Substituents
  • Coumarin o-glycoside
  • Coumarin-7-o-glycoside
  • Phenolic glycoside
  • Hydroxycoumarin
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Benzenoid
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.95%; H 4.74%; O 42.32%DFC
Melting PointMp 213-214°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -104 (dioxan)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCichoriin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6936000000-3189ea8a0aabc709aeebSpectrum
Predicted GC-MSCichoriin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2353029000-f90429c99944a173ba08Spectrum
Predicted GC-MSCichoriin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCichoriin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0906000000-f762a68df017c1e2cf1b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-fb12040f73f72a76812c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g0-1900000000-2fbb8c50f201999f6a462015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1729000000-89269076594cc9193b202015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-f1a95af0387b6dde5f7c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2900000000-d654c6d1bd26299bd5e42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0309000000-7684d5d21391172250be2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1933000000-ec0486672b0ede4e73742021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-6940000000-c10070d68baed2c2b5672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-3d14bcc6eb929d3218362021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2924000000-9461161dbf99995329962021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fs-1900000000-3c148183cdf12f6071e22021-09-23View Spectrum
NMRNot Available
ChemSpider ID4265025
ChEMBL IDNot Available
KEGG Compound IDC09206
Pubchem Compound ID5088914
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30821
CRC / DFC (Dictionary of Food Compounds) IDCNP29-S:CNP32-O
EAFUS IDNot Available
Dr. Duke IDCICHORIIN
BIGG IDNot Available
KNApSAcK IDC00002458
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 / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti feedantDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.