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Showing Compound Cyanidin 3,5-diglucoside (FDB002597)

Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2019-11-26 02:57:40 UTC
Primary IDFDB002597
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3,5-diglucoside
DescriptionCyanidin 3,5-diglucoside 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. Cyanidin 3,5-diglucoside is found, on average, in the highest concentration within a few different foods, such as white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.), cabbages (Brassica oleracea var. capitata), and black elderberries (Sambucus nigra) and in a lower concentration in pomegranates (Punica granatum) and common beans (Phaseolus vulgaris). Cyanidin 3,5-diglucoside has also been detected, but not quantified in, several different foods, such as garden onions (Allium cepa), redcurrants (Ribes rubrum), chives (Allium schoenoprasum), malus (crab apple), and grapes (Vitis). This could make cyanidin 3,5-diglucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3,5-diglucoside.
CAS Number2611-67-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Cyanenindb_source
Cyanidin 3,5-diglucosidedb_source
Cyanindb_source
Shisonin Adb_source
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP-0.18ALOGPS
logP-2.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area272.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity148.4 m³·mol⁻¹ChemAxon
Polarizability58.35 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H31O16
IUPAC name2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C27H30O16/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32)/p+1/t17?,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1
InChI KeyRDFLLVCQYHQOBU-QZTFBGFRSA-O
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC3=C(O[C@@H]4OC(CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight611.5254
Monoisotopic Molecular Weight611.161209944
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
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.03%; H 5.11%; O 41.86%DFC
Melting PointMp 203-204° (chloride)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -258 (HCl aq.)DFC
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, Positivesplash10-03di-0100009000-b715f4da249bc24ca6792016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-2600089000-9918cc8163362e7fa6002016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900130000-d067f93d7b9c9925623b2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1200009000-8ba97a109b647725d1d32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-5700019000-2dafd8cdc16bb9acf2b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100200000-a1b33d50ed6fc0682daa2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID441688
Pubchem Substance IDNot Available
ChEBI ID3978
Phenol-Explorer ID71
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDODW40-I:CMQ11-F
EAFUS IDNot Available
Dr. Duke IDCYANIDIN-3,5-DI-O-GLUCOSIDE|CYANIDIN-3,5-DIGLUCOSIDE|CYANIN
BIGG IDNot Available
KNApSAcK IDC00002378
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 ID71
Duplicate IDSNot Available
Old DFC IDSCMQ73-Z:CMQ11-F
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti polio22587 An agent that prevents poliovirus infection, inducing immunity to protect against poliomyelitis. Therapeutically, it is used to prevent and control polio outbreaks, commonly administered through vaccination to promote herd immunity and eradicate the disease.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
EmeticAn agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Pigment26130 A biological coloring agent, playing a role in skin and eye protection. Therapeutically, pigments are used in photodynamic therapy and skin camouflage. Medically, they are used to treat conditions like vitiligo, albinism, and skin discoloration, as well as in diagnostic imaging and wound healing applications.DUKE
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).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.