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Showing Compound Dimalonylawobanin (FDB001590)

Record Information
Version1.0
Creation date2010-04-08 22:05:01 UTC
Update date2019-11-26 02:56:36 UTC
Primary IDFDB001590
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDimalonylawobanin
DescriptionDimalonylawobanin is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Dimalonylawobanin is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Dimalonylawobanin can be found in hyssop, which makes dimalonylawobanin a potential biomarker for the consumption of this food product.
CAS Number128508-49-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.49ALOGPS
logP1.43ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area405.86 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity222.92 m³·mol⁻¹ChemAxon
Polarizability87.88 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H41O25
IUPAC name5-{[(2S,3R,4R,5S,6R)-5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C42H40O25/c43-18-4-1-16(2-5-18)3-6-30(51)60-14-26-34(55)35(56)37(58)41(65-26)64-25-11-20-23(62-39(25)17-7-21(45)33(54)22(46)8-17)9-19(44)10-24(20)63-42-38(59)36(57)40(67-32(53)13-29(49)50)27(66-42)15-61-31(52)12-28(47)48/h1-11,26-27,34-38,40-42,55-59H,12-15H2,(H6-,43,44,45,46,47,48,49,50,51,54)/p+1/t26-,27-,34-,35+,36-,37-,38-,40-,41-,42-/m1/s1
InChI KeyLVWQQRKFDAHVIR-KJEREKKNSA-O
Isomeric SMILESO[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC3=C(C=C(O)C=C3O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](OC(=O)CC(O)=O)[C@H](O)[C@H]3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O
Average Molecular Weight945.7599
Monoisotopic Molecular Weight945.193691862
Classification
Description Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 3-O-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Flavonoid 3-o-6-p-coumaroyl-glycoside
  • Anthocyanidin-3-o-glycoside
  • Anthocyanin
  • Anthocyanidin-5-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Pentacarboxylic acid or derivatives
  • Phenolic glycoside
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Styrene
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Oxane
  • Monosaccharide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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, Positivesplash10-03dj-0000000009-b60f92cc17ab5c456bb62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000009-7520019fff5ee14a14a52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-7301305069-8b238418ccf7257f8beb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1000000009-e8d8a9707998d4a269df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9300000018-bb7c0db2407896fc26dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9600002000-58db016190c893d4aa3a2016-08-03View 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 IDC00006888
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.