Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2019-11-27 17:07:07 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 annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Cyanidin 3,5-diglucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number2611-67-8
Structure
Thumb
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • 2-furanone
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100009000-b715f4da249bc24ca679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-2600089000-9918cc8163362e7fa600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900130000-d067f93d7b9c9925623bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1200009000-8ba97a109b647725d1d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-5700019000-2dafd8cdc16bb9acf2b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100200000-a1b33d50ed6fc0682daaView in MoNA
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 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
emeticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.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.