Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2015-07-20 21:30:29 UTC
Primary IDFDB000229
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGallic acid 3-O-gallate
DescriptionDigallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve either -meta or -para depside bonds. [Wikipedia]
CAS Number536-08-3
Structure
Thumb
Synonyms
SynonymSource
Gallic acid 3-monogallateChEBI
Gallate 3-monogallateGenerator
Gallic acid 3-monogallic acidGenerator
Gallate 3-O-gallateGenerator
Gallic acid 3-O-gallic acidGenerator
Gallic acid 5,6-dihydroxy-3-carboxyphenyl esterMeSH
Digallic aciddb_source
m-Digallic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.28ALOGPS
logP2.42ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.02 m³·mol⁻¹ChemAxon
Polarizability29.07 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H10O9
IUPAC name3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid
InChI IdentifierInChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)
InChI KeyCOVFEVWNJUOYRL-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C1
Average Molecular Weight322.225
Monoisotopic Molecular Weight322.032481902
Classification
DescriptionThis compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Galloyl ester
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Phenol ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoic acid
  • Catechol
  • Benzoyl
  • Phenoxy compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-99dc70c2502325372598View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-01b9-1009003000-cd8acb11ec0152f73253View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0739000000-04e8b3e46aa76053cc6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0932000000-54a763c58dbe078119b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3910000000-f9a95cbd1ede0185b416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0449000000-24813c6833d97ef0ef4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0953000000-5e2c3c2d517061d39a78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-1900000000-5bc32bc1d2843a063327View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01572
Pubchem Compound ID341
Pubchem Substance IDNot Available
ChEBI ID30814
Phenol-Explorer ID438
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMT08-Y:CMT08-Y
EAFUS IDNot Available
Dr. Duke IDDIGALLIC-ACID|M-DIGALLIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDigallic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.