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Showing Compound Delphinidin 3-arabinoside (FDB017192)

Record Information
Version1.0
Creation date2010-04-08 22:12:56 UTC
Update date2019-11-26 03:14:23 UTC
Primary IDFDB017192
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDelphinidin 3-arabinoside
DescriptionDelphinidin 3-arabinoside 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-arabinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Delphinidin 3-arabinoside is found, on average, in the highest concentration in a few different foods, such as bilberries, highbush blueberries, and lowbush blueberries and in a lower concentration in . Delphinidin 3-arabinoside has also been detected, but not quantified in, several different foods, such as american cranberries, black chokeberries, lingonberries, sparkleberries, and blackcurrants. This could make delphinidin 3-arabinoside a potential biomarker for the consumption of these foods.
CAS Number28500-01-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Delphinidin 3-arabinosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.35ALOGPS
logP0.78ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area193.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.28 m³·mol⁻¹ChemAxon
Polarizability41.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H19O11
IUPAC name3-{[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C20H18O11/c21-6-15-17(27)18(28)20(31-15)30-14-5-9-10(23)3-8(22)4-13(9)29-19(14)7-1-11(24)16(26)12(25)2-7/h1-5,15,17-18,20-21,27-28H,6H2,(H4-,22,23,24,25,26)/p+1/t15-,17+,18-,20+/m0/s1
InChI KeyWIEYMFHXYNRELM-ZNWBIBPKSA-O
Isomeric SMILESOC[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]1O
Average Molecular Weight435.3583
Monoisotopic Molecular Weight435.09273645
Classification
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.18%; H 4.40%; O 40.42%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelphinidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9103200000-528bff0460288422ec1fSpectrum
Predicted GC-MSDelphinidin 3-arabinoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002r-6910128000-05cc5d5c9a55b6deb642Spectrum
Predicted GC-MSDelphinidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelphinidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0100900000-cfbce2d34297134d9e202016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-1300900000-960e93c80bfdaf41cf532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-9602000000-5a79501d8679d383ee172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1100900000-f45c828e6fb218872ad02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2700900000-5bac816d979b7210fb652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-8910000000-c6cccf5a8fe21b55d4732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0670-0008900000-13564c825935f5bf261d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0109700000-c31c644689c8c20e9b272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3297000000-41967221fa5bb7b938f12021-09-22View Spectrum
NMRNot Available
ChemSpider ID30777225
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25087690
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID29
DrugBank IDNot Available
HMDB IDHMDB37998
CRC / DFC (Dictionary of Food Compounds) IDOJK30-N:KWN28-C
EAFUS IDNot Available
Dr. Duke IDDELPHINIDIN-3-O-ARABINOSIDE|DELPHINIDIN-3-O-ALPHA-L-ARABINOSIDE
BIGG IDNot Available
KNApSAcK IDC00006696
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID29
Duplicate IDSNot Available
Old DFC IDSCMR96-N:KWN28-C
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).