Procyanidin C1 3',3''-digallate (CHEM031716)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:52:02 UTC
Update Date2016-11-09 01:19:19 UTC
Accession NumberCHEM031716
Identification
Common NameProcyanidin C1 3',3''-digallate
ClassSmall Molecule
Descriptionent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate is found in fruits. ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate is a constituent of Byrsonima crassifolia (nance) bark.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ent-Epicatechin-(4a->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallateGenerator
ent-Epicatechin-(4a->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallic acidGenerator
ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallic acidGenerator
ent-Epicatechin-(4α->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallateGenerator
ent-Epicatechin-(4α->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4beta->8)-3-O-galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Procyanidin C1 3',3''-di-O-gallateHMDB
2-(3,4-Dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Epicatechin-(4b->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallateGenerator
Epicatechin-(4b->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4beta->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4β->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallateGenerator
Epicatechin-(4β->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallic acidGenerator
Chemical FormulaC59H46O26
Average Molecular Mass1170.981 g/mol
Monoisotopic Mass1170.228 g/mol
CAS Registry Number106533-61-3
IUPAC Name2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
SMILESOC1C(OC2=CC(O)=CC(O)=C2C1C1=C2OC(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(C3=C(O)C=C(O)C4=C3OC(C(C4)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC(O)=C(O)C=C3)C2=C(O)C=C1O)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C59H46O26/c60-24-14-33(68)43-41(15-24)81-53(20-2-5-27(62)31(66)8-20)51(78)47(43)44-35(70)18-36(71)46-48(57(85-59(80)23-12-39(74)50(77)40(75)13-23)54(84-56(44)46)21-3-6-28(63)32(67)9-21)45-34(69)17-29(64)25-16-42(82-58(79)22-10-37(72)49(76)38(73)11-22)52(83-55(25)45)19-1-4-26(61)30(65)7-19/h1-15,17-18,42,47-48,51-54,57,60-78H,16H2
InChI KeyCSQVLCNLSUIXDX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin gallate
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP4.25ALOGPS
logP7.61ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area464.66 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity290.55 m³·mol⁻¹ChemAxon
Polarizability111.39 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-eabc7f3469d3847a4879Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ftu-4911200211-5122fbbb04ac8de34249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-1940000000-0c3d556c2aea45c437f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000004-be9723a2b4699f2adacdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0wmm-5900000001-d14a35e98db9a51a2b8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2901100000-013b032a0da88764fd50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-5800000090-a3febf930788e2295effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f92-4800053692-b64d0831842e15734361Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-1800093260-193e3ed96ce76b469a83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w90-9800000020-3c5802e7b527a83319e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ukc-4910100020-6e0da4a7fcfc771beafdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-5910000030-3f309ce8494cf5777d21Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038371
FooDB IDFDB021146
Phenol Explorer IDNot Available
KNApSAcK IDC00009228
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014555
ChEBI IDNot Available
PubChem Compound ID73822578
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.