Showing Compound Card for Cyanidin 3-glucoside (CDB005211)

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Record Information
Version1.0
Created at2020-04-17 19:20:28 UTC
Updated at2020-11-18 16:39:32 UTC
CannabisDB IDCDB005211
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCyanidin 3-glucoside
DescriptionCyanidin 3-glucoside, also known as asterin? or chrysontemin, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peachs, tartary buckwheats, soft-necked garlics, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. An anthocyanin cation that is a cyanidin cation linked to a beta-D-glucosyl moiety at position 3. Cyanidin 3-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cyanidin 3-O-glucosideChEBI
Cyanidin 3-O-beta-D-glucosideKegg
Cyanidin 3-O-b-D-glucosideGenerator
Cyanidin 3-O-β-D-glucosideGenerator
ChrysonteminHMDB
Cyanidin 3-monoglucosideHMDB
Cyanidol 3-glucosideHMDB
GlucocyanidinHMDB
KuromamineHMDB
Cyanidin 3-O-glucopyranosideMeSH
Cyanidin 3-O-beta-D-glucopyranosideMeSH
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyryliumHMDB
2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyryliumHMDB
3-(beta-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chlorideHMDB
3-(β-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chlorideHMDB
3-(β-D-Glucopyranosyloxy)-3’,4’,5,7-tetrahydroxyflavylium chlorideHMDB
3-O-(beta-D-Glucopyranosyl)cyanidinHMDB
3-O-(β-D-Glucopyranosyl)cyanidinHMDB
AsterinHMDB
ChrysantheminHMDB
ChrysantheninHMDB
Cyanidin 3-O-beta-glucopyranosideHMDB
Cyanidin 3-O-beta-glucosideHMDB
Cyanidin 3-O-glucoside chlorideHMDB
Cyanidin 3-O-β-D-glucopyranosideHMDB
Cyanidin 3-O-β-glucopyranosideHMDB
Cyanidin 3-O-β-glucosideHMDB
Cyanidin 3-beta-D-O-glucosideHMDB
Cyanidin 3-beta-D-glucopyranosideHMDB
Cyanidin 3-beta-O-glucosideHMDB
Cyanidin 3-beta-glucopyranosideHMDB
Cyanidin 3-beta-glucosideHMDB
Cyanidin 3-beta-glucoside cationHMDB
Cyanidin 3-glucosideHMDB
Cyanidin 3-glucoside chlorideHMDB
Cyanidin 3-β-D-O-glucosideHMDB
Cyanidin 3-β-D-glucopyranosideHMDB
Cyanidin 3-β-O-glucosideHMDB
Cyanidin 3-β-glucopyranosideHMDB
Cyanidin 3-β-glucosideHMDB
Cyanidin 3-β-glucoside cationHMDB
KuromaninHMDB
KuromanineHMDB
Chemical FormulaC21H21O11
Average Molecular Weight449.38
Monoisotopic Molecular Weight449.1084
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
Traditional Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
CAS Registry Number47705-70-4
SMILES
OC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17-,18+,19-,21-/m1/s1
InChI KeyRKWHWFONKJEUEF-GQUPQBGVSA-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
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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
logP0.98ALOGPS
logP0.39ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area193.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.26 m³·mol⁻¹ChemAxon
Polarizability43.14 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-MSCyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001r-9613500000-4ecd805029dccd975fedSpectrum
Predicted GC-MSCyanidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-6620019000-8d5ae8efad054c2ab4aaSpectrum
Predicted GC-MSCyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, TMS_3_50, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, TMS_4_64, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, TMS_4_66, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, TMS_5_55, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-glucoside, "Cyanidin 3-glucoside,3TMS,#50" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0012-0190300000-fa49c39b10bc818caf382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0170-0982400000-bf6abe51e9ef29f65fe02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0190000000-1d3575fd8a5bad57646c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0940000000-688e280b84a3b096281c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001s-0090200000-abde441c456e0554b97b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-d8c555166d10dec1fb482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-0ee5168148d1f43f98b92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-1dc5f0ee658f46d936df2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 31V, positivesplash10-000i-0090000000-62b9d786642d936137722020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 31V, positivesplash10-000i-0090000000-503a1596bd2451e838d72020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090200000-d45f62202546a09960c42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0190000000-86b08922db000308f1b52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0890000000-f54a34d80fd4bb859a262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0061900000-b3d22fc8233274bb4ac22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0091200000-218723bb02667d2114f52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009i-2091100000-e8b2df5780fffa75ac4a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0030684
DrugBank IDNot Available
Phenol Explorer Compound ID9
FoodDB IDFDB002603
KNApSAcK IDC00053092
Chemspider ID390284
KEGG Compound IDC08604
BioCyc IDCPD1F-766
BiGG IDNot Available
Wikipedia LinkChrysanthemin
METLIN IDNot Available
PubChem Compound4481259
PDB IDNot Available
ChEBI ID28426
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91