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Showing Compound Cyanidin 3-(disinapoylsophoroside) 5-glucoside (FDB017164)

Record Information
Version1.0
Creation date2010-04-08 22:12:52 UTC
Update date2019-11-26 03:14:19 UTC
Primary IDFDB017164
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-(disinapoylsophoroside) 5-glucoside
DescriptionCyanidin 3-(disinapoylsophoroside) 5-glucoside belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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. Cyanidin 3-(disinapoylsophoroside) 5-glucoside has been detected, but not quantified in, brassicas and cauliflowers (Brassica oleracea var. botrytis). This could make cyanidin 3-(disinapoylsophoroside) 5-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3-(disinapoylsophoroside) 5-glucoside.
CAS Number110202-93-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.51ALOGPS
logP1.42ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area441.26 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity289.77 m³·mol⁻¹ChemAxon
Polarizability113.91 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC55H61O29
IUPAC name3-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C55H60O29/c1-72-31-11-22(12-32(73-2)41(31)62)5-9-39(60)76-20-37-44(65)47(68)50(71)54(82-37)84-52-48(69)45(66)38(21-77-40(61)10-6-23-13-33(74-3)42(63)34(14-23)75-4)83-55(52)80-35-18-26-29(78-51(35)24-7-8-27(58)28(59)15-24)16-25(57)17-30(26)79-53-49(70)46(67)43(64)36(19-56)81-53/h5-18,36-38,43-50,52-56,64-71H,19-21H2,1-4H3,(H4-,57,58,59,60,61,62,63)/p+1/t36-,37-,38-,43-,44-,45-,46+,47+,48+,49-,50-,52-,53-,54+,55+/m1/s1
InChI KeyOMKHCRCKDGASQY-SYFUIQBDSA-O
Isomeric SMILESCOC1=CC(\C=C\C(=O)OC[C@H]2O[C@@H](O[C@H]3[C@@H](OC4=C([O+]=C5C=C(O)C=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C5=C4)C4=CC(O)=C(O)C=C4)O[C@H](COC(=O)\C=C\C4=CC(OC)=C(O)C(OC)=C4)[C@@H](O)[C@@H]3O)[C@H](O)[C@@H](O)[C@@H]2O)=CC(OC)=C1O
Average Molecular Weight1186.0554
Monoisotopic Molecular Weight1185.32985099
Classification
Description Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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 ParentAnthocyanidin 3-O-6-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Anthocyanidin 3-o-6-p-coumaroyl-glycoside
  • Anthocyanin
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • 1-benzopyran
  • Styrene
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Catechol
  • Methoxybenzene
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Heteroaromatic compound
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Ether
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

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, Positivesplash10-000i-0930000000-34964c31acb6bbf004772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1940000000-0e6b37b08e8aab6511372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ika-4910000000-e82271ffeea93e3fbea32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1910000000-42947d350db3fe9be0da2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-3940000001-4f8f3e8a58e0fe302c612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-fe2afa2c75c32a7fc0b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-2920000000-fd7abdc801999cf69ed32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ay1-9841006343-a91239ff749ac086553e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ky0-0790000022-6f3644073ab34b90fab42021-09-22View Spectrum
NMRNot Available
ChemSpider ID30777221
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 IDHMDB37979
CRC / DFC (Dictionary of Food Compounds) IDODW40-I:KWM76-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006854
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 IDSCMQ73-Z:KWM76-K
Associated Foods
FoodContent Range AverageReference
CauliflowerExpected but not quantifiedNot AvailableKNAPSACK
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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.