2.0 2012-08-09 09:16:19 -0600 2015-06-03 17:21:33 -0600 ECMDB21461 M2MDB001856 Pyrroloquinoline quinone Enzymes containing PQQ are called quinoproteins. PQQ and quinoproteins play a role in the redox metabolism and structural integrity of cells and tissues [PMID:2558842]. It was reported that aminoadipate semialdehyde dehydrogenase (AASDH) might also use PQQ as a cofactor, suggesting a possibility that PQQ is a vitamin in mammals. [PMID:12712191] 2,7,9-Tricarboxy-1H-pyrrolo[2,3-f]quinoline-4,5-dione Methoxatin PQQ Pyrrolo-quinoline quinone Pyrroloquinoline-quinone C14H6N2O8 330.206 330.012415178 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid pyrroloquinoline quinone 72909-34-3 OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24) MMXZSJMASHPLLR-UHFFFAOYSA-N Solid Cytoplasm logp 0.46 ALOGPS logs -3.53 ALOGPS solubility 9.66e-02 g/l ALOGPS logp 0.37 ChemAxon pka_strongest_acidic 0.68 ChemAxon pka_strongest_basic 4.46 ChemAxon iupac 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid ChemAxon average_mass 330.206 ChemAxon mono_mass 330.012415178 ChemAxon smiles OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O ChemAxon formula C14H6N2O8 ChemAxon inchi InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24) ChemAxon inchikey MMXZSJMASHPLLR-UHFFFAOYSA-N ChemAxon polar_surface_area 174.72 ChemAxon refractivity 74.53 ChemAxon polarizability 28.91 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 9 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17671 Specdb::CMs 40144 Specdb::CMs 165584 Specdb::NmrOneD 320271 Specdb::NmrOneD 320272 Specdb::NmrOneD 320273 Specdb::NmrOneD 320274 Specdb::NmrOneD 320275 Specdb::NmrOneD 320276 Specdb::NmrOneD 320277 Specdb::NmrOneD 320278 Specdb::NmrOneD 320279 Specdb::NmrOneD 320280 Specdb::NmrOneD 320281 Specdb::NmrOneD 320282 Specdb::NmrOneD 320283 Specdb::NmrOneD 320284 Specdb::NmrOneD 320285 Specdb::NmrOneD 320286 Specdb::NmrOneD 320287 Specdb::NmrOneD 320288 Specdb::NmrOneD 320289 Specdb::NmrOneD 320290 Specdb::MsMs 28970 Specdb::MsMs 28971 Specdb::MsMs 28972 Specdb::MsMs 35528 Specdb::MsMs 35529 Specdb::MsMs 35530 Specdb::MsMs 2448428 Specdb::MsMs 2448429 Specdb::MsMs 2448430 Specdb::MsMs 2486517 Specdb::MsMs 2486518 Specdb::MsMs 2486519 HMDB13636 0 997 C00113 18315 PQQ Pyrroloquinoline_quinone van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Kasahara, T., Kato, T. (2003). "Nutritional biochemistry: A new redox-cofactor vitamin for mammals." Nature 422:832. 12712191 Paz, M. A., Fluckiger, R., Torrelio, B. M., Gallop, P. M. (1989). "Methoxatin (PQQ), coenzyme for copper-dependent amine and mixed-function oxidation in mammalian tissues." Connect Tissue Res 20:251-257. 2558842 Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml