CHEBI:30778 - gallic acid

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ChEBI Name gallic acid
ChEBI ID CHEBI:30778
Definition A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5268, CHEBI:24180
Supplier Information ChemicalBook:CB0158671, eMolecules:493996, ZINC000000001504
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Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates". Its name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does not contain gallium.
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Formula C7H6O5
Net Charge 0
Average Mass 170.11954
Monoisotopic Mass 170.02152
InChI InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
InChIKey LNTHITQWFMADLM-UHFFFAOYSA-N
SMILES OC(=O)c1cc(O)c(O)c(O)c1
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606) Found in faeces (UBERON:0001988). See: PubMed
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor
A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33).
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
Application(s): astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing gallic acid (CHEBI:30778) has role antineoplastic agent (CHEBI:35610)
gallic acid (CHEBI:30778) has role antioxidant (CHEBI:22586)
gallic acid (CHEBI:30778) has role apoptosis inducer (CHEBI:68495)
gallic acid (CHEBI:30778) has role astringent (CHEBI:74783)
gallic acid (CHEBI:30778) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
gallic acid (CHEBI:30778) has role EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor (CHEBI:64996)
gallic acid (CHEBI:30778) has role geroprotector (CHEBI:176497)
gallic acid (CHEBI:30778) has role human xenobiotic metabolite (CHEBI:76967)
gallic acid (CHEBI:30778) has role plant metabolite (CHEBI:76924)
gallic acid (CHEBI:30778) is a trihydroxybenzoic acid (CHEBI:27115)
gallic acid (CHEBI:30778) is conjugate acid of gallate (CHEBI:16918)
Incoming (−)-catechin-3-O-gallate (CHEBI:76131) has functional parent gallic acid (CHEBI:30778)
(−)-epicatechin-(4α→8)-(−)-epicatechin-3'-O-gallate (CHEBI:75660) has functional parent gallic acid (CHEBI:30778)
(−)-epicatechin-3-O-gallate (CHEBI:70255) has functional parent gallic acid (CHEBI:30778)
(−)-gallocatechin gallate (CHEBI:156271) has functional parent gallic acid (CHEBI:30778)
(+)-catechin-3-O-gallate (CHEBI:76132) has functional parent gallic acid (CHEBI:30778)
(+)-epicatechin-3-O-gallate (CHEBI:76126) has functional parent gallic acid (CHEBI:30778)
(+)-gallocatechin gallate (CHEBI:156284) has functional parent gallic acid (CHEBI:30778)
1,2,6-tris-O-galloyl-β-D-glucose (CHEBI:27395) has functional parent gallic acid (CHEBI:30778)
2-galloyl-D-glucose (CHEBI:136559) has functional parent gallic acid (CHEBI:30778)
3-O-methylgallic acid (CHEBI:28647) has functional parent gallic acid (CHEBI:30778)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) has functional parent gallic acid (CHEBI:30778)
digallic acid (CHEBI:30814) has functional parent gallic acid (CHEBI:30778)
ellagic acid (CHEBI:4775) has functional parent gallic acid (CHEBI:30778)
eugeniin (CHEBI:4916) has functional parent gallic acid (CHEBI:30778)
gallate ester (CHEBI:37576) has functional parent gallic acid (CHEBI:30778)
gallotannin (CHEBI:24182) has functional parent gallic acid (CHEBI:30778)
galloyl α-D-glucose (CHEBI:49215) has functional parent gallic acid (CHEBI:30778)
galloyl β-D-glucose (CHEBI:24183) has functional parent gallic acid (CHEBI:30778)
procyanidin B1 3'-O-gallate (CHEBI:75653) has functional parent gallic acid (CHEBI:30778)
procyanidin B1 3-O-gallate (CHEBI:75651) has functional parent gallic acid (CHEBI:30778)
procyanidin B2 3'-O-gallate (CHEBI:75647) has functional parent gallic acid (CHEBI:30778)
procyanidin B2 3-O-gallate (CHEBI:75652) has functional parent gallic acid (CHEBI:30778)
procyanidin B3 3'-O-gallate (CHEBI:75662) has functional parent gallic acid (CHEBI:30778)
procyanidin B3 3-O-gallate (CHEBI:75656) has functional parent gallic acid (CHEBI:30778)
procyanidin B4 3'-O-gallate (CHEBI:75655) has functional parent gallic acid (CHEBI:30778)
procyanidin B4 3-O-gallate (CHEBI:75663) has functional parent gallic acid (CHEBI:30778)
syringic acid (CHEBI:68329) has functional parent gallic acid (CHEBI:30778)
tannic acid (CHEBI:75211) has functional parent gallic acid (CHEBI:30778)
theogallin (CHEBI:9522) has functional parent gallic acid (CHEBI:30778)
gallate (CHEBI:16918) is conjugate base of gallic acid (CHEBI:30778)
IUPAC Name
3,4,5-trihydroxybenzoic acid
Synonyms Sources
3,4,5-trihydroxybenzoic acid ChEBI
3,4,5-Trihydroxybenzoic acid KEGG COMPOUND
Gallic acid KEGG COMPOUND
Pyrogallol-5-carboxylic acid KEGG COMPOUND
Manual Xrefs Databases
C00002647 KNApSAcK
C01424 KEGG COMPOUND
CPD-183 MetaCyc
Gallic_acid Wikipedia
HMDB0005807 HMDB
LSM-37191 LINCS
View more database links
Registry Numbers Types Sources
149-91-7 CAS Registry Number KEGG COMPOUND
149-91-7 CAS Registry Number ChemIDplus
149-91-7 CAS Registry Number NIST Chemistry WebBook
2050274 Reaxys Registry Number Reaxys
27336 Gmelin Registry Number Gmelin
Citations Waiting for Citations
Last Modified
26 October 2021