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Delphinidin 3-glucoside (FDB017191)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0feb-9602600000-45aed3fc2911f95c79ebSpectrum
Predicted GC-MSDelphinidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-5510009000-d60ac3b75f44a32e605bSpectrum
Predicted GC-MSDelphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_3_54, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_4_71, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_4_81, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_4_87, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_4_88, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_76, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_82, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_83, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_87, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_88, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_5_91, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_6_58, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_6_59, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_6_62, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, TMS_6_63, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-glucoside, "Delphinidin 3-glucoside,3TMS,#54" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0139400000-820d95dd9b931186bf3c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009100000-900e146ee03a33c5e31c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0091300000-9658b19c1d3c3ad887752021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0100900000-78712e7fc63bf2f6c41c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-1300900000-174d36b448e52a2ab4a12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7902100000-1c91ff38e96e02e42e962016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300900000-0ea3c4becf795cde3fa22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6800900000-cf4c9c44468a096638482016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-05d37d94d7cc9ad734d72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aos-0006900000-ff93644803a0dd8e09fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0039400000-bcb4b7e5729a0597c0af2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-5398200000-c60c5f9ebfd4dff713d02021-09-22View Spectrum
NMRNot Available
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.