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Showing Compound Chakaflavonoside A (FDB001788)

Record Information
Version1.0
Creation date2010-04-08 22:05:06 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001788
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChakaflavonoside A
Description(2S,3R,4S,5R,6R)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.
CAS Number1063877-20-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.48 g/LALOGPS
logP0.56ALOGPS
logP-1.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area429.89 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity242.29 m³·mol⁻¹ChemAxon
Polarizability102.03 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H58O27
IUPAC name(2S,3R,4S,5R,6R)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C48H58O27/c1-17-30(56)41(73-46-37(63)35(61)31(57)25(14-49)69-46)39(65)45(67-17)66-16-27-33(59)42(74-47-38(64)36(62)32(58)26(15-50)70-47)44(72-28(55)11-4-18-2-7-20(51)8-3-18)48(71-27)75-43-34(60)29-23(54)12-22(53)13-24(29)68-40(43)19-5-9-21(52)10-6-19/h2-13,17,25-27,30-33,35-54,56-59,61-65H,14-16H2,1H3/b11-4+/t17-,25+,26+,27+,30-,31+,32+,33+,35-,36-,37+,38+,39+,40?,41+,42-,43?,44+,45+,46-,47-,48-/m0/s1
InChI KeyCIKCLUGAOKEOQY-BVVCZVLZSA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](OC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O
Average Molecular Weight1066.9579
Monoisotopic Molecular Weight1066.31654665
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Flavonoid-3-o-glycoside
  • Flavanone
  • Flavanonol
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Coumaric acid ester
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Fatty acid ester
  • Benzenoid
  • Fatty acyl
  • Oxane
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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, Positivesplash10-000j-7590000565-ab40d5fa000a4a5eccac2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1690010831-c6f3a96ee1928678bafb2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-1940001611-43034aadc2354e1b2cf42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0hg2-9852000546-4731d255569ec3e37f122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pa-4941000222-7c027e53aa3d455146282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ds-1920000101-607db3593d61bf3198ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-944cf86a3bd1308558d52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-4900000000-c5d9b991729bd817fbe82021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000002-ebe3f526bfba5f3fe9582021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-756bbbd127af03f7bbec2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-8900000000-8a3780e471a72b0c919e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0400000009-0dfbb61da55f9c2857f22021-10-21View 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 IDC00029929
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.