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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:10 UTC
Update Date2017-12-07 02:56:24 UTC
HMDB IDHMDB0029247
Secondary Accession Numbers
  • HMDB29247
Metabolite Identification
Common NameDelphinidin 3-(6''-malonyl-glucoside)
DescriptionDelphinidin 3-(6''-malonyl-glucoside) 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. Delphinidin 3-(6''-malonyl-glucoside) is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, delphinidin 3-(6''-malonyl-glucoside) is primarily located in the cytoplasm. Delphinidin 3-(6''-malonyl-glucoside) can be converted into delphinidin.
Structure
Thumb
Synonyms
ValueSource
Delphinidin 3-O-(6-O-malonyl-beta-D-glucoside)ChEBI
Delphinidin 3-O-(6-O-malonyl-b-D-glucoside)Generator
Delphinidin 3-O-(6-O-malonyl-β-D-glucoside)Generator
Delphinidin 3-(6''-malonylglucoside)HMDB
Delphinidin 3-O-(6''-malonyl-glucoside)HMDB
Delphinidin 3-O-(6''-malonylglucoside)HMDB
Chemical FormulaC24H23O15
Average Molecular Weight551.4304
Monoisotopic Molecular Weight551.103695066
IUPAC Name3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium
Traditional Name3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C24H22O15/c25-9-3-11(26)10-5-15(23(37-14(10)4-9)8-1-12(27)19(32)13(28)2-8)38-24-22(35)21(34)20(33)16(39-24)7-36-18(31)6-17(29)30/h1-5,16,20-22,24,33-35H,6-7H2,(H5-,25,26,27,28,29,30,32)/p+1/t16-,20-,21+,22-,24-/m1/s1
InChI KeyFNFHDAUGLIPVPU-XQKZCQIMSA-O
Chemical Taxonomy
DescriptionThis compound 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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1,3-dicarbonyl compound
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

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
Water Solubility0.56 g/LALOGPS
logP1.02ALOGPS
logP0.39ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area257.04 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.73 m³·mol⁻¹ChemAxon
Polarizability50.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-9332430000-76257bff6794403f7fbbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0059-6296058000-ae1bce4074e508b8ed59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000090000-54fb784fc9200033b7e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000090000-4b43a263219b9f9571c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvn-8913040000-e13e15c88e3f21730c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1000090000-046145af1665f57da4f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9100070000-eeeeb667a73cf03608deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9510000000-3b307ca8a26635ca86f8View in MoNA
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
FoodDB IDFDB000072
KNApSAcK IDC00006877
Chemspider ID10362664
KEGG Compound IDC16301
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14311158
PDB IDNot Available
ChEBI ID55334
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]