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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:14:38 UTC
Update Date2022-03-07 02:55:35 UTC
HMDB IDHMDB0037973
Secondary Accession Numbers
  • HMDB37973
Metabolite Identification
Common NameCyanidin 3,3',5-triglucoside
DescriptionCyanidin 3,3',5-triglucoside 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. Cyanidin 3,3',5-triglucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3,3',5-triglucoside has been detected, but not quantified in, fruits and pineapples. This could make cyanidin 3,3',5-triglucoside a potential biomarker for the consumption of these foods.
Structure
Data?1563863118
Synonyms
ValueSource
Cyanidin 3,3',5-tri-O-glucosideHMDB
Cyanidin 3,5,3'-tri-O-glucosideHMDB
Cyanidin 3,5,3'-triglucosideHMDB
Chemical FormulaC33H41O21
Average Molecular Weight773.666
Monoisotopic Molecular Weight773.214033374
IUPAC Name7-hydroxy-2-(4-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium
Traditional Name7-hydroxy-2-(4-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium
CAS Registry Number88110-66-1
SMILES
OCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(CO)C(O)C(O)C4O)C=C23)C2=CC(OC3OC(CO)C(O)C(O)C3O)=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C33H40O21/c34-7-18-21(39)24(42)27(45)31(52-18)49-15-5-11(37)4-14-12(15)6-17(51-33-29(47)26(44)23(41)20(9-36)54-33)30(48-14)10-1-2-13(38)16(3-10)50-32-28(46)25(43)22(40)19(8-35)53-32/h1-6,18-29,31-36,39-47H,7-9H2,(H-,37,38)/p+1
InChI KeyZOEXTKFPTHFWDY-UHFFFAOYSA-O
Chemical Taxonomy
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-3p-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.56 g/LALOGPS
logP-0.91ALOGPS
logP-4.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area351.74 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity180.55 m³·mol⁻¹ChemAxon
Polarizability73.66 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-286.00630932474
DeepCCS[M+Na]+260.7430932474
AllCCS[M+H]+254.532859911
AllCCS[M+H-H2O]+254.232859911
AllCCS[M+NH4]+254.632859911
AllCCS[M+Na]+254.632859911
AllCCS[M-H]-252.332859911
AllCCS[M+Na-2H]-256.132859911
AllCCS[M+HCOO]-260.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cyanidin 3,3',5-triglucosideOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(CO)C(O)C(O)C4O)C=C23)C2=CC(OC3OC(CO)C(O)C(O)C3O)=C(O)C=C2)C(O)C(O)C1O6005.2Standard polar33892256
Cyanidin 3,3',5-triglucosideOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(CO)C(O)C(O)C4O)C=C23)C2=CC(OC3OC(CO)C(O)C(O)C3O)=C(O)C=C2)C(O)C(O)C1O6586.6Standard non polar33892256
Cyanidin 3,3',5-triglucosideOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(CO)C(O)C(O)C4O)C=C23)C2=CC(OC3OC(CO)C(O)C(O)C3O)=C(O)C=C2)C(O)C(O)C1O7118.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TMS_1_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanidin 3,3',5-triglucoside GC-MS (TBDMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 10V, Positive-QTOFsplash10-00di-0100001900-89e0d1476ef95043bd532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 20V, Positive-QTOFsplash10-0uk9-0200000900-ca1d6c19fea644bb2aae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 40V, Positive-QTOFsplash10-08fv-7900007200-f6a27dc7dab35da8fe3e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 10V, Negative-QTOFsplash10-00di-1100000900-92aa3372ea53e3ab747e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 20V, Negative-QTOFsplash10-00xr-4500001900-87e7d5f710a4f32f6c332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 40V, Negative-QTOFsplash10-0006-9100011000-c09c3a69eeaba105460b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 10V, Positive-QTOFsplash10-01ot-0200629300-88cf5e1880d57e8eaca12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 20V, Positive-QTOFsplash10-03dj-2200759600-aa5db772e2084f92e80f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanidin 3,3',5-triglucoside 40V, Positive-QTOFsplash10-03ea-7900344100-782eafbfc4ecc42999bd2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017150
KNApSAcK IDC00002377
Chemspider ID3679420
KEGG Compound IDC08629
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4481465
PDB IDNot Available
ChEBI ID28215
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .