Record Information
Version1.0
Creation date2010-04-08 22:12:56 UTC
Update date2020-09-17 15:41:08 UTC
Primary IDFDB017191
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDelphinidin 3-glucoside
DescriptionDelphinidin 3-glucoside, also known as myrtillin, 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. Delphinidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Delphinidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries, blackcurrants, and summer grapes and in a lower concentration in common beans, lowbush blueberries, and red raspberries. Delphinidin 3-glucoside has also been detected, but not quantified in, several different foods, such as eggplants, fruits, rubus (blackberry, raspberry), sweet cherries, and black chokeberries. This could make delphinidin 3-glucoside a potential biomarker for the consumption of these foods. An anthocyanin cation consisting of delphinidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.
CAS Number6906-38-3
Structure
Thumb
Synonyms
SynonymSource
Delfinidin 3-O-beta-D-glucosideChEBI
Delphinidin 3-O-glucosideChEBI
MirtillinKegg
Delphinidin 3-O-beta-D-glucosideKegg
Delfinidin 3-O-b-D-glucosideGenerator
Delfinidin 3-O-β-D-glucosideGenerator
Delphinidin 3-O-b-D-glucosideGenerator
Delphinidin 3-O-β-D-glucosideGenerator
Delphinidin 3-monoglucosideHMDB
Delphinidin 3-O-beta-D-glucopyranosideHMDB
Delphinidol 3-glucosideHMDB
MyrtillinHMDB
Myrtillin aHMDB
Delphinidin 3-O-glucopyranosideHMDB
Delphinidin 3-O-beta-glucosideHMDB
Delphinidin-3-glucosideHMDB
Delphinidin 3-glucosidedb_source
Myrtillin Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP0.93ALOGPS
logP0.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area213.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity118.24 m³·mol⁻¹ChemAxon
Polarizability43.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H21O12
IUPAC name5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1
InChI KeyXENHPQQLDPAYIJ-PEVLUNPASA-O
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight465.3842
Monoisotopic Molecular Weight465.103301136
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Tetracarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • 1,3-dicarbonyl compound
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.20%; H 4.55%; O 41.25%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0feb-9602600000-45aed3fc2911f95c79ebJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-5510009000-d60ac3b75f44a32e605bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0139400000-820d95dd9b931186bf3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009100000-900e146ee03a33c5e31cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0100900000-78712e7fc63bf2f6c41cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-1300900000-174d36b448e52a2ab4a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7902100000-1c91ff38e96e02e42e96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300900000-0ea3c4becf795cde3fa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6800900000-cf4c9c44468a09663848JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-05d37d94d7cc9ad734d7JSpectraViewer
ChemSpider ID10716855
ChEMBL IDNot Available
KEGG Compound IDC12138
Pubchem Compound ID13915667
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID27
DrugBank IDNot Available
HMDB IDHMDB37997
CRC / DFC (Dictionary of Food Compounds) IDOJK30-N:KWN26-A
EAFUS IDNot Available
Dr. Duke IDMYRTILLIN|DELPHINIDIN-3-0-BETA-D-GLUCOSIDE|DELPHINIDIN-3-O-BETA-GLUCOSIDE|DELPHINIDIN-3-GLUCOSIDE|DELPHINIDIN-3-MONOGLUCOSIDE|DELPHINIDIN-3-O-GLUCOSIDE|DELPHINIDIN-3-O-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006697
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 ID28
Duplicate IDS
Old DFC IDSCMR96-N:KWN26-A
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
hypoglycemic35526 A drug which lowers the blood glucose level.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— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.