2.0 2012-05-31 14:49:40 -0600 2015-06-03 17:20:11 -0600 ECMDB20539 M2MDB001346 Crotonobetainyl-CoA Crotonobetainyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure) (9R,20E)-1-(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-N,N,N,8,8-pentamethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosph adocos-20-en-22-aminium 3,5-dioxide (non-preferred name) (E)-4-(trimethylammonio)but-2-enoyl-coenzyme A (E)-4-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-4-oxobut-2-enyl-trimethylazanium (e)-4-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-4-oxobut-2-enyl-trimethylazanium Crotonobetainyl-CoA Crotonobetainyl-coenzyme A C28H48N8O17P3S 893.71 893.207097376 [(2E)-4-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobut-2-en-1-yl]trimethylazanium [(2E)-4-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobut-2-en-1-yl]trimethylazanium [H]\C(C[N+](C)(C)C)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(=O)(O)O InChI=1S/C28H47N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h6-7,15-17,21-23,27,39-40H,8-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1/b7-6+/t17-,21-,22-,23+,27-/m1/s1 WAUPBDVHJXXZGW-HXPULJKESA-O Cytosol logp -1.19 ALOGPS logs -2.29 ALOGPS solubility 4.74e+00 g/l ALOGPS logp -7.5 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.79 ChemAxon iupac [(2E)-4-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobut-2-en-1-yl]trimethylazanium ChemAxon average_mass 893.71 ChemAxon mono_mass 893.207097376 ChemAxon smiles [H]\C(C[N+](C)(C)C)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(=O)(O)O ChemAxon formula C28H48N8O17P3S ChemAxon inchi InChI=1S/C28H47N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h6-7,15-17,21-23,27,39-40H,8-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1/b7-6+/t17-,21-,22-,23+,27-/m1/s1 ChemAxon inchikey WAUPBDVHJXXZGW-HXPULJKESA-O ChemAxon polar_surface_area 370.61 ChemAxon refractivity 212.99 ChemAxon polarizability 82.51 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 19 ChemAxon donor_count 9 ChemAxon physiological_charge -1 ChemAxon formal_charge 1 ChemAxon L-carnitine degradation I In the absence of exogenous electron acceptors like nitrate, nitrite, fumarate, dimethyl sulfoxide or trimethylamine-N-oxide, the addition of L-carnitine stimulates the anaerobic growth of E. coli. During anaerobic growth in the presence of carbon and nitrogen sources, E. coli is able to catalyze the dehydration and reduction of L-carnitine to γ-butyrobetaine via a cyclic pathway of CoA-linked intermediates. The carbon and nitrogen skeleton of carnitine is not assimilated. The carnitine pathway may play more than one role in the cell: generation of an osmoprotectant and generation of an external electron acceptor in anaerobic respiration. (EcoCyc) PW002037 Metabolic carnitine degradation I CARNMET-PWY Specdb::NmrOneD 269098 Specdb::NmrOneD 269099 Specdb::NmrOneD 269100 Specdb::NmrOneD 269101 Specdb::NmrOneD 269102 Specdb::NmrOneD 269103 Specdb::NmrOneD 269104 Specdb::NmrOneD 269105 Specdb::NmrOneD 269106 Specdb::NmrOneD 269107 Specdb::NmrOneD 269108 Specdb::NmrOneD 269109 Specdb::NmrOneD 269110 Specdb::NmrOneD 269111 Specdb::NmrOneD 269112 Specdb::NmrOneD 269113 Specdb::NmrOneD 269114 Specdb::NmrOneD 269115 Specdb::NmrOneD 269116 Specdb::NmrOneD 269117 Specdb::MsMs 1255066 Specdb::MsMs 1255067 Specdb::MsMs 1255068 591 571 CROTONOBETAINYL-COA Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Carnitinyl-CoA dehydratase P31551 CAID_ECOLI caiD http://ecmdb.ca/proteins/P31551.xml Crotonobetainyl-CoA:carnitine CoA-transferase P31572 CAIB_ECOLI caiB http://ecmdb.ca/proteins/P31572.xml Crotonobetainyl-CoA dehydrogenase P60584 CAIA_ECOLI caiA http://ecmdb.ca/proteins/P60584.xml Probable crotonobetaine/carnitine-CoA ligase P31552 CAIC_ECOLI caiC http://ecmdb.ca/proteins/P31552.xml L-Carnitinyl-CoA <> Crotonobetainyl-CoA + Water CARNDETRU-RXN Adenosine triphosphate + Coenzyme A + Crotonobetaine > ADP + Crotonobetainyl-CoA + Phosphate Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine L-Carnitinyl-CoA > Crotonobetainyl-CoA + Water CARNDETRU-RXN gamma-Butyrobetainyl-CoA + an oxidized electron acceptor <> Crotonobetainyl-CoA + a reduced electron acceptor CROBETREDUCT-RXN Crotonobetainyl-CoA + reduced electron acceptor > gamma-Butyrobetainyl-CoA + oxidized electron acceptor PW_R005952 D-Carnitinyl-CoA > Crotonobetainyl-CoA + Water PW_R005951