Showing Compound Card for Delphinidin 3-glucoside (CDB005209)

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Record Information
Version1.0
Created at2020-04-17 19:20:16 UTC
Updated at2020-11-18 16:39:32 UTC
CannabisDB IDCDB005209
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Delphinidin 3-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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, MeSH
Delphinidol 3-glucosideHMDB
MyrtillinHMDB, MeSH
Myrtillin aHMDB
Delphinidin 3-O-glucopyranosideMeSH, HMDB
Delphinidin 3-O-beta-glucosideMeSH, HMDB
Delphinidin-3-glucosideMeSH, HMDB
Chemical FormulaC21H21O12
Average Molecular Weight465.38
Monoisotopic Molecular Weight465.1033
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
Traditional 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
CAS Registry Number6906-38-3
SMILES
OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0037997
DrugBank IDNot Available
Phenol Explorer Compound ID27
FoodDB IDFDB017191
KNApSAcK IDC00006698
Chemspider ID391783
KEGG Compound IDC12138
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDelphinidin-3-O-glucoside
METLIN IDNot Available
PubChem Compound13915667
PDB IDNot Available
ChEBI ID31463
References
General ReferencesNot Available