2.0 2012-08-09 09:25:32 -0600 2015-06-03 17:21:48 -0600 ECMDB21572 M2MDB001966 Succinate-semialdehyde-thiamine PPi Succinate-semialdehyde-thiamine pyrophosphate is a thiamine derivative. The first intermediate (SHCHC) in the menaquinone biosynthetic pathway, requires two reactions. The first is the decarboxylation of alpha-ketoglutarate by an alpha-ketoglutarate decarboxylase, which results in the formation of succinic semialdehyde-thiamine PPi (TPP) anion, and the second is the addition of the succinic semialdehyde-TPP anion to isochorismate, which is carried out by the enzyme SHCHC synthase. Both enzymatic activities are encoded by the menD gene [PMID: 1459959] Succinic acid-semialdehyde-thiamine ppi Succinic semialdehyde-thiamine pyrophosphate Succinic semialdehyde-thiamine pyrophosphoric acid C16H22N4O10P2S 524.379 524.053186658 5-[2-({[(3-carboxylato-1-hydroxypropyl phosphonato)oxy]phosphinato}oxy)ethyl]-3-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium 5-(2-{[(3-carboxylato-1-hydroxypropyl phosphonato)oxyphosphinato]oxy}ethyl)-3-[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium CC1=C(CCOP([O-])(=O)OP([O-])(=O)OC(O)CCC([O-])=O)SC=[N+]1CC1=CN=C(C)NC1=N InChI=1S/C16H24N4O10P2S/c1-10-13(33-9-20(10)8-12-7-18-11(2)19-16(12)17)5-6-28-31(24,25)30-32(26,27)29-15(23)4-3-14(21)22/h7,9,15,23H,3-6,8H2,1-2H3,(H4-,17,18,19,21,22,24,25,26,27)/p-2 JUWXHVVKSHTJQQ-UHFFFAOYSA-L Cytoplasm logp -0.99 ALOGPS logs -3.39 ALOGPS solubility 2.51e-01 g/l ALOGPS logp -8.3 ChemAxon pka_strongest_acidic 1.72 ChemAxon pka_strongest_basic 7.04 ChemAxon iupac 5-[2-({[(3-carboxylato-1-hydroxypropyl phosphonato)oxy]phosphinato}oxy)ethyl]-3-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium ChemAxon average_mass 524.379 ChemAxon mono_mass 524.053186658 ChemAxon smiles CC1=C(CCOP([O-])(=O)OP([O-])(=O)OC(O)CCC([O-])=O)SC=[N+]1CC1=CN=C(C)NC1=N ChemAxon formula C16H22N4O10P2S ChemAxon inchi InChI=1S/C16H24N4O10P2S/c1-10-13(33-9-20(10)8-12-7-18-11(2)19-16(12)17)5-6-28-31(24,25)30-32(26,27)29-15(23)4-3-14(21)22/h7,9,15,23H,3-6,8H2,1-2H3,(H4-,17,18,19,21,22,24,25,26,27)/p-2 ChemAxon inchikey JUWXHVVKSHTJQQ-UHFFFAOYSA-L ChemAxon polar_surface_area 220.43 ChemAxon refractivity 133.68 ChemAxon polarizability 45.63 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 10 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 319751 Specdb::NmrOneD 319752 Specdb::NmrOneD 319753 Specdb::NmrOneD 319754 Specdb::NmrOneD 319755 Specdb::NmrOneD 319756 Specdb::NmrOneD 319757 Specdb::NmrOneD 319758 Specdb::NmrOneD 319759 Specdb::NmrOneD 319760 Specdb::NmrOneD 319761 Specdb::NmrOneD 319762 Specdb::NmrOneD 319763 Specdb::NmrOneD 319764 Specdb::NmrOneD 319765 Specdb::NmrOneD 319766 Specdb::NmrOneD 319767 Specdb::NmrOneD 319768 Specdb::NmrOneD 319769 Specdb::NmrOneD 319770 Specdb::MsMs 29450 Specdb::MsMs 29451 Specdb::MsMs 29452 Specdb::MsMs 36008 Specdb::MsMs 36009 Specdb::MsMs 36010 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 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P17109 MEND_ECOLI menD http://ecmdb.ca/proteins/P17109.xml