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Carlinoside (FDB001558)

Record Information
Version1.0
Creation date2010-04-08 22:05:01 UTC
Update date2019-11-26 02:56:35 UTC
Primary IDFDB001558
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCarlinoside
DescriptionCarlinoside, also known as luteolin 6-C-glucoside-8-C-arabinoside or 6-C-B-D-glucosyl-8-C-A-L-arabinopyranosylluteolin, is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Carlinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Carlinoside can be found in a number of food items such as green bell pepper, orange bell pepper, yellow bell pepper, and red bell pepper, which makes carlinoside a potential biomarker for the consumption of these food products.
CAS Number59952-97-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.23 g/LALOGPS
logP-0.75ALOGPS
logP-2.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area267.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity135.17 m³·mol⁻¹ChemAxon
Polarizability55.36 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H28O15
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C26H28O15/c27-5-13-18(33)21(36)23(38)26(41-13)15-19(34)14-10(30)4-12(7-1-2-8(28)9(29)3-7)40-24(14)16(20(15)35)25-22(37)17(32)11(31)6-39-25/h1-4,11,13,17-18,21-23,25-29,31-38H,5-6H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1
InChI KeyXBGYTZHKGMCEGE-VYUBKLCTSA-N
Isomeric SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C([C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1
Average Molecular Weight580.4915
Monoisotopic Molecular Weight580.142820226
Classification
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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, Positivesplash10-03e9-0000190000-2450d43c11e4848e43402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1500490000-5680c8c8b3f03115406a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07bs-2105950000-c07dcc5f25c44a73419d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000390000-149494eabad65b3bcfbd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08or-6301790000-46605de8614708adc7282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9102410000-ad51de8420121e5237b82016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10026
Pubchem Compound ID442584
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 IDCARLINOSIDE
BIGG IDNot Available
KNApSAcK IDC00006184
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
Insectiphile24852 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
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
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).