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Showing Compound Apigeninidin 5-(5''-caffeylarabinoside) (FDB001569)

Record Information
Version1.0
Creation date2010-04-08 22:05:01 UTC
Update date2019-11-26 02:56:35 UTC
Primary IDFDB001569
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApigeninidin 5-(5''-caffeylarabinoside)
DescriptionApigeninidin 5-(5''-caffeylarabinoside) is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Apigeninidin 5-(5''-caffeylarabinoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apigeninidin 5-(5''-caffeylarabinoside) can be found in sorghum, which makes apigeninidin 5-(5''-caffeylarabinoside) a potential biomarker for the consumption of this food product.
CAS Number131400-98-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0079 g/LALOGPS
logP3.85ALOGPS
logP4.76ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area179.28 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity149.86 m³·mol⁻¹ChemAxon
Polarizability55.98 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H25O11
IUPAC name5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C29H24O11/c30-17-5-3-16(4-6-17)22-9-7-19-23(38-22)12-18(31)13-24(19)39-29-28(36)27(35)25(40-29)14-37-26(34)10-2-15-1-8-20(32)21(33)11-15/h1-13,25,27-29,35-36H,14H2,(H3-,30,31,32,33,34)/p+1/t25-,27-,28+,29+/m0/s1
InChI KeyBBZCRSFPHPHYKT-ANHREMPLSA-O
Isomeric SMILESO[C@H]1[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC(O)=CC3=C2C=CC(=[O+]3)C2=CC=C(O)C=C2)[C@@H]1O
Average Molecular Weight549.5022
Monoisotopic Molecular Weight549.139686642
Classification
Description Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-5-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-5-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Pentose monosaccharide
  • Benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monosaccharide
  • Fatty acyl
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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, Positivesplash10-0udi-0000090000-a57cba00c590d5024cb32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000090000-3e15c0392461319266d32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lei-0770950000-061e101e3b0aaa176c012016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-f9407df7d5e9b82dd1e32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-ee39c1c820e88bd6fd252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pvi-9861060000-295d17d72b481af0f3fc2016-08-03View 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 IDC00006753
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
Processing...
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.