Gallocatechin 3-gallate (CED0006422)

Record Information
Version1.0
Creation Date2016-05-26 05:09:50 UTC
Update Date2026-04-06 02:02:29 UTC
Accession NumberCHEM034729
Identification
Common NameGallocatechin 3-gallate
ClassSmall Molecule
Description
Gallocatechin 3-gallate is an organic compound with the formula C22H18O11 and an average molecular weight of 458.37 g/mol. Gallocatechin 3-gallate belongs to the flavans, a subclass of flavonoids within the organic compounds. It is further categorized under the superclass of phenylpropanoids and polyketides. This compound is found in or released from 14 recorded sources across various sectors. In the energy, oil & gas and industrial manufacturing & chemical processing sectors, it is associated with lubricants. Within the healthcare, pharmaceuticals & veterinary products sector, it is linked to medical devices. It is also found in textiles, leather & furnishings, specifically in carpets, rugs, and synthetic textiles. In the food, food processing & cookware sector, it is related to food packaging and the preparation of vinegar. Additionally, it is present in electrical & electronic equipment, including batteries, capacitors, printed circuit boards, wires and cables, cell phones, and one other source. One additional sector is also recorded. Recorded exposure routes for gallocatechin 3-gallate include oral, inhalation, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Gallocatechin-3-O-gallateChEBI
(+)-Gallocatechol gallateChEBI
(2R,3S)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoateChEBI
(+)-Gallocatechin-3-O-gallic acidGenerator
(+)-Gallocatechol gallic acidGenerator
(2R,3S)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
(+)-Gallocatechin 3-O-gallateHMDB
Gallocatechin 3-gallateHMDB
Gallocatechin 3-O-gallateHMDB
Gallocatechin 3-O-gallic acidGenerator
Gallocatechin gallateMeSH
Gallocatechin-3-gallateMeSH
Gallocatechin 3-gallic acidGenerator
Chemical FormulaC22H18O11
Average Molecular Mass458.372 g/mol
Monoisotopic Mass458.085 g/mol
CAS Registry Number5127-64-0
IUPAC Name(2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Namegallocatechin 3-O-gallate
SMILESOC1=CC(O)=C2C[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1
InChI IdentifierInChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m0/s1
InChI KeyWMBWREPUVVBILR-GHTZIAJQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechin gallates
Alternative Parents
Substituents
  • Catechin gallate
  • Epigallocatechin
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP2.38ALOGPS
logP3.08ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.75 m³·mol⁻¹ChemAxon
Polarizability42.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ug0-0930000000-f01263ac8498e09a9b96Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-1490207000-3bb9d44478f3c302740fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0910400000-db9be0eef8a50d2a2e94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-0900000000-0559ca217784c4585897Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-2900000000-1f6e2b3e327778bfdb78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0301900000-ce04b1666eb710d5a6beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0690-0915600000-95f0d4e98c44ec0a42d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-0900000000-db1b45028af945572cc3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0003900000-8f91dc75ff31c110b853Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kw0-0911300000-cfe0a1ddf5316282d1abNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00vr-1914200000-6052bd4777f8f2b91366Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4u-0161900000-93fcf1085dda87e2eef3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pvr-0974800000-fe2b35b2b9c1b0d68fc8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fs9-0925100000-97364265724fdd2727cbNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2622.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAlpha-(1,3)-fucosyltransferase 4P22083HumansPredicted (SEA)0.0778492
Click to view 3D structure3-oxoacyl-(Acyl-carrier protein) reductaseQ8I2S7Plasmodium falciparum (isolate 3D7)Predicted (SEA)0.0778492
Latent membrane protein 1 structureClick to view 3D structureLatent membrane protein 1P03230HHV-4Predicted (SEA)0.0778492
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)0.0778492
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)0.0778492
Click to view 3D structureGlucose-6-phosphate 1-dehydrogenaseP11412Saccharomyces cerevisiae S288cPredicted (SEA)0.0778492
Click to view 3D structureEnoyl-acyl-carrier protein reductaseQ965D5Plasmodium falciparumPredicted (SEA)0.0778492
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)0.0778492
Proteasome subunit beta type-5 structureClick to view 3D structureProteasome subunit beta type-5P28074HumansPredicted (SEA)0.0778492
Click to view 3D structureFatty acid synthaseQ965D7Plasmodium falciparumPredicted (SEA)0.0778492
Click to view 3D structure3-oxoacyl-acyl-carrier protein reductaseQ965D6Plasmodium falciparumPredicted (SEA)0.0778492
6-phosphogluconate dehydrogenase, decarboxylating structureClick to view 3D structure6-phosphogluconate dehydrogenase, decarboxylatingP52209HumansPredicted (SEA)0.0778492
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)4.9045
DNA repair protein RAD52 homolog structureClick to view 3D structureDNA repair protein RAD52 homologP43351HumansPredicted (SEA)0.0778492
Apoptosis regulator Bcl-2 structureClick to view 3D structureApoptosis regulator Bcl-2P10415HumansPredicted (SEA)9.03051
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)6.46149
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)2.80257
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)1.63483
Pyruvate kinase PKM structureClick to view 3D structurePyruvate kinase PKMP14618HumansPredicted (SEA)0.233548
NAD kinase structureClick to view 3D structureNAD kinaseO95544HumansPredicted (SEA)0.0778492
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)0.856341
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)26.9358
Membrane-associated tyrosine- and threonine-specific cdc2-inhibitory kinase structureClick to view 3D structureMembrane-associated tyrosine- and threonine-specific cdc2-inhibitory kinaseQ99640HumansPredicted (SEA)4.9045
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI structureClick to view 3D structureEnoyl-[acyl-carrier-protein] reductase [NADH] FabIP0AEK4Escherichia coli (strain K12)Predicted (SEA)0.0778492
A disintegrin and metalloproteinase with thrombospondin motifs 4 structureClick to view 3D structureA disintegrin and metalloproteinase with thrombospondin motifs 4O75173HumansPredicted (SEA)6.30579
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0041598
FooDB IDFDB021740
Phenol Explorer ID137
KNApSAcK IDC00008882
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4440832
ChEBI ID156284
PubChem Compound ID5276890
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10929811
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18318450
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.