Showing Compound Card for Pelargonidin 3-glucoside (CDB005076)

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Record Information
Version1.0
Created at2020-04-17 19:06:55 UTC
Updated at2020-11-18 16:39:17 UTC
CannabisDB IDCDB005076
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePelargonidin 3-glucoside
DescriptionPelargonidin 3-glucoside, also known as callistephin, 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. Pelargonidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). An anthocyanin cation consisting of pelargonidin having a beta-D-glucosyl residue attached at the 3-hydroxy position. Pelargonidin 3-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chlorideChEBI
3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium chlorideChEBI
CallistephinChEBI
Pelargonidin 3-O-glucosideChEBI
Pelargonidin-3-glucopyranosideChEBI
Pelargonidin-3-glucosideChEBI
Pelargonidin 3-O-beta-D-glucosideKegg
3-(b-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chlorideGenerator
3-(Β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chlorideGenerator
3-(b-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium chlorideGenerator
3-(Β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium chlorideGenerator
Pelargonidin 3-O-b-D-glucosideGenerator
Pelargonidin 3-O-β-D-glucosideGenerator
3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyryliumHMDB
3-(Β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyryliumHMDB
Pelargonidin 3-O-beta-glucopyranosideHMDB
Pelargonidin 3-O-β-glucopyranosideHMDB
Pelargonidin-3-gluHMDB
Pelargonidin 3-glucosideChEBI
Chemical FormulaC21H21O10
Average Molecular Weight433.39
Monoisotopic Molecular Weight433.1129
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
CAS Registry Number47684-27-5
SMILES
OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
InChI KeyABVCUBUIXWJYSE-GQUPQBGVSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • Hydroxyflavonoid
  • Flavanone
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Chromone
  • Arylsulfate
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Monocyclic benzene moiety
  • Organic sulfuric acid or derivatives
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
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
logP1.13ALOGPS
logP0.67ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity114.28 m³·mol⁻¹ChemAxon
Polarizability42.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPelargonidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-8c4c8cb400c69dc5402f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0090100000-0bdf5ac7e7a90ec92dbc2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-00di-0090100000-bac3e73111b9504ef0702020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0090200000-e3619fa9e4dc0e0e21892020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0090000000-f4cc1241c2b149391f352020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00di-0590000000-fc9c2a1e64d858840e092020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-014i-0290200000-e03b57d8b34b084fddf32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-014i-0290000000-fd9fe1e8d736e15b51f52020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-014i-0190100000-8f8974a5ba5a286e6aa22020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-001i-0020900000-3c089ef6816df553bb0b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-001i-0030900000-a09a2f2df69a0f02c9f82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0089-0050900000-57f694607d80fe25f4c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00e9-0090400000-1d3899b32c1bbce014812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-0090000000-2f0ad7488f7b51cdf07e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-0090000000-7245a9d5b27c2375ec8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00di-0090000000-ae2d276f9bf988b2c2952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-00di-0090000000-4adbfb04d499f904a4082020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00di-0090000000-4310fa4f41ee10c49bdc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00di-0090000000-e5141ed51da558186d0b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-00di-0090000000-21adaaa6ae277c2666a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-00di-0090000000-a399659b6faa31f958672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-00di-0090000000-f7915fa355bd4a22a7732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-00di-0090000000-8a0f321e912cf537cf7c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-00di-0090000000-3ab39f5d138ff24ae0202020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 30V, positivesplash10-00di-0090000000-53d43948c6c87f6fa0332020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0240551
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00006630
Chemspider ID391782
KEGG Compound IDC12137
BioCyc IDPELARGONIDIN-3-GLUCOSIDE-CMPD
BiGG IDNot Available
Wikipedia LinkCallistephin
METLIN IDNot Available
PubChem Compound443648
PDB IDNot Available
ChEBI ID31967
References
General ReferencesNot Available