Compound: aurintricarboxylic acid
SMILES: O=C1C(C(=O)O)=CC(=C(c2cc(c(O)cc2)C(=O)O)c3cc(c(O)cc3)C(=O)O)C=C1
InChIKey: GIXWDMTZECRIJT-UHFFFAOYSA-N
Synonyms: aurintricarboxylic acid, 4431-00-9, Aluminon free acid, aurin tricarboxylic acid, NP9O8E29QW, Benzoic acid, 5-((3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl)-2-hydroxy-, CHEBI:87397, Benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy-, Acid, Aurintricarboxylic, RefChem:560355, Acid, Aurin Tricarboxylic, 5,5'-((3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene)bis(2-hydroxybenzoic acid), MFCD00011663, 5-[(3-carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid, MLS002153482, 5,5'-(3-Carboxy-4-oxocyclohexa-2,5-dienylidenemethylene)di(salicylic acid), 1,4-Cyclohexadiene-1-carboxylic acid, 3-(bis(3-carboxy-4-hydroxyphenyl)methylene)-6-oxo-, 3,3'-[(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid), SMR000326731, 1,4-Cyclohexadiene-1-carboxylic acid, 3-[bis(3-carboxy-4-hydroxyphenyl)methylene]-6-oxo-, Benzoic acid, 3,3'-((3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene)bis(6-hydroxy-, 5-[(3-carboxy-4-hydroxy-phenyl)-(3-carboxy-4-oxo-cyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxocyclohexa-2,5-dienylidene)methyl ]-2-hydroxybenzoic acid, Aurintricarboxylic Acids (Technical Grade), NSC643698, aurine tricarboxylic acid, SR-01000075661, C22H14O9, NSC 4056, EINECS 224-628-1, BRN 2228904, 3,3'-[(3-Carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxybenzoic acid], Dupont ATA, 3,3'-((3-CARBOXY-4-OXO-2,5-CYCLOHEXADIEN-1-YLIDENE)METHYLENE)BIS(6-HYDROXYBENZOIC ACID), Lopac-A-1895, UNII-NP9O8E29QW, Aurintricarboxylicacid(ATA), chrome violet CG free acid, cid_2259, Aurintricarboxylic acid(ATA), Lopac0_000054, SCHEMBL98495, 4-10-00-04161 (Beilstein Handbook Reference), SPECTRUM1505163, CHEMBL275938, orb1299026, DTXSID9063453, SCHEMBL29353681, SCHEMBL29450069, BDBM60996, HMS3260K09, CAC 1098, NSC-4056, Tox21_500054, SBB005410, AKOS015969706, AT15393, CCG-204149, LP00054, SDCCGSBI-0050042.P002, Dupont DA 639 (SD-095345), NCGC00015040-01, NCGC00015040-02, NCGC00015040-03, NCGC00015040-04, NCGC00015040-05, NCGC00015040-06, NCGC00015040-08, NCGC00093568-01, NCGC00096052-01, NCGC00096052-02, NCGC00260739-01, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid, DA-61324, MS-27411, ST057219, CP 005240, HY-122575, CS-0087159, EU-0100054, NS00031410, A 1895, EN300-226544, J-022987, Q4822390, SR-01000075661-1, SR-01000075661-7, Aurintricarboxylic acid, practical grade, >=85% (titration), powder, 5,5'-((3-Carboxy-4-oxocyclohexa-2,5-dienylidene)methylene)bis(2-hydroxybenzoic acid), 5-[(3-carboxy-4-hydroxy-phenyl)-(3-carboxy-4-keto-cyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxo-1-cyclohexa-2,5-dienylidene)methyl]-2-hydroxybenzoic acid, 5-[(3-carboxy-4-oxidanylidene-cyclohexa-2,5-dien-1-ylidene)-(3-carboxy-4-oxidanyl-phenyl)methyl]-2-oxidanyl-benzoic acid, Benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl) (3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy-
Theoretical properties:
molecular_formula: C22H14O9
molecular_weight: 422.3 g/mol
exact_mass: 422.06378202 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 5
heavy_atom_count: 31
topological_polar_surface_area: 169 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Aurintricarboxylic acid is a member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'. It has a role as a fluorochrome, an insulin-like growth factor receptor 1 antagonist and a histological dye. It is a monohydroxybenzoic acid, a tricarboxylic acid and a member of quinomethanes. It is a conjugate acid of an aurintricarboxylate.", "chebi": "A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.", "chembl": "AURINTRICARBOXYLIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Aurintricarboxylic acid (ATA) is a chemical compound that readily polymerizes in aqueous solution, forming a stable free radical that inhibits protein-nucleic acid interactions. It is a potent inhibitor of ribonuclease and topoisomerase II by preventing the binding of the nucleic acid to the enzyme. It stimulates tyrosine phosphorylation processes including the Jak2/STAT5 pathway in NB2 lymphoma cells, ErbB4 in neuroblastoma cells, and MAP kinases, Shc proteins, phosphatidylinositide 3-kinase and phospholipase C\u03b3 in PC12 cells. It also inhibits apoptosis. It prevents down-regulation of Ca2+-impermeable GluR2 receptors and inhibits calpain, a Ca2+-activated protease that is activated during apoptosis.\nIt is used to inhibit protein biosynthesis in its initial stages.  Nominally, it is used in biological experiments as a protein inhibitor, and as an ammonium salt (known as aluminon) it is used as a reagent to estimate the aluminium in water, biological tissue, and foods.\nIt was found that ATA is a strong inhibitor of topoisomerases and other nucleases. It might be useful for increasing efficiency of RNA isolation.\nIt has been discovered that using aurintricarboxylic acid against influenza-A post-infection has a strong protective effect by inhibiting the virus' ability to reproduce. In cultured canine kidney cells, it was found to reduce viral reproduction and infection when applied post-infection, but not when used as a 'vaccine'. It has also been shown to block the binding of the HIV coat molecule gp120 to the CD4 co-receptor on T cells through which it invades.\nAurintricarboxylic acid and its ammonium salt shows antiviral activity in vitro against coronaviruses such as SARS, MERS and SARS-CoV-2, and while it is unlikely to have suitable properties to be developed as a medicine in its own right, it has proved useful in scientific research into novel antiviral drugs to combat these diseases."}