2.0 2012-05-31 14:20:52 -0600 2015-06-03 17:19:02 -0600 ECMDB12184 M2MDB000825 Adenosyl cobinamide phosphate Adenosyl cobinamide phosphate, a known intermediate of the de novo biosynthetic pathway, is involved in Porphyrin and chlorophyll metabolism.In Salmonella typhimurium LT2, under anaerobic conditions, CobU (EC 2.7.7.62 and EC 2.7.1.156), CobT (EC 2.4.2.21), CobC (EC 3.1.3.73) and CobS (EC 2.7.8.26) catalyse reactions in the nucleotide loop Adenosyl cobinamide phosphoric acid Adenosylcobinamide-P C58H85CoN16O14P 1320.3013 1319.550078214 (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)OP(=O)(O)O InChI=1S/C48H74N11O11P.C10H12N5O3.Co/c1-23(70-71(67,68)69)22-55-38(66)16-17-45(6)29(18-35(52)63)43-48(9)47(8,21-37(54)65)28(12-15-34(51)62)40(59-48)25(3)42-46(7,20-36(53)64)26(10-13-32(49)60)30(56-42)19-31-44(4,5)27(11-14-33(50)61)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43H,10-18,20-22H2,1-9H3,(H16,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;4-,6-,7-,10-;/m11./s1 MQCMBMUJJHSGIF-QMUWONGRSA-M Solid Cytosol logp -0.04 ALOGPS logs -5.16 ALOGPS solubility 1.01e-02 g/l ALOGPS logp -14 ChemAxon pka_strongest_acidic 1.51 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide ChemAxon average_mass 1320.3013 ChemAxon mono_mass 1319.550078214 ChemAxon smiles C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)OP(=O)(O)O ChemAxon formula C58H85CoN16O14P ChemAxon inchi InChI=1S/C48H74N11O11P.C10H12N5O3.Co/c1-23(70-71(67,68)69)22-55-38(66)16-17-45(6)29(18-35(52)63)43-48(9)47(8,21-37(54)65)28(12-15-34(51)62)40(59-48)25(3)42-46(7,20-36(53)64)26(10-13-32(49)60)30(56-42)19-31-44(4,5)27(11-14-33(50)61)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43H,10-18,20-22H2,1-9H3,(H16,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;4-,6-,7-,10-;/m11./s1 ChemAxon inchikey MQCMBMUJJHSGIF-QMUWONGRSA-M ChemAxon polar_surface_area 485.98 ChemAxon refractivity 330.2 ChemAxon polarizability 131.82 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 18 ChemAxon donor_count 12 ChemAxon physiological_charge -1 ChemAxon formal_charge 1 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1 Specdb::NmrOneD 11502 Specdb::NmrOneD 11503 Specdb::NmrOneD 11504 Specdb::NmrOneD 11505 Specdb::NmrOneD 11506 Specdb::NmrOneD 11507 Specdb::NmrOneD 11508 Specdb::NmrOneD 11509 Specdb::NmrOneD 11510 Specdb::NmrOneD 11511 Specdb::NmrOneD 11512 Specdb::NmrOneD 11513 Specdb::NmrOneD 11514 Specdb::NmrOneD 11515 Specdb::NmrOneD 11516 Specdb::NmrOneD 11517 Specdb::NmrOneD 11518 Specdb::NmrOneD 11519 Specdb::NmrOneD 11520 Specdb::NmrOneD 11521 Specdb::MsMs 1247578 Specdb::MsMs 1247579 Specdb::MsMs 1247580 Specdb::MsMs 2508622 Specdb::MsMs 2508623 Specdb::MsMs 2508624 HMDB12184 23724501 C06509 2481 ADENOSYLCOBINAMIDE-P 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 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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 Bifunctional adenosylcobalamin biosynthesis protein cobU P0AE76 COBU_ECOLI cobU http://ecmdb.ca/proteins/P0AE76.xml Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ion R05221 COBINAMIDEKIN-RXN Adenosyl cobinamide phosphate + Guanosine triphosphate + Hydrogen ion > Adenosylcobinamide-GDP + Pyrophosphate R05222 COBINPGUANYLYLTRANS-RXN Adenosyl cobinamide + Adenosine triphosphate <> Adenosyl cobinamide phosphate + ADP R05221 Adenosyl cobinamide phosphate + Guanosine triphosphate <> Adenosylcobinamide-GDP + Pyrophosphate R05222 Adenosyl cobinamide + Guanosine triphosphate <> Adenosyl cobinamide phosphate + Guanosine diphosphate R06558 Adenosine triphosphate + Guanosine triphosphate + Adenosyl cobinamide <> Adenosyl cobinamide phosphate + ADP + Guanosine diphosphate R05221 R06558 Adenosyl cobinamide + Adenosine triphosphate > Adenosyl cobinamide phosphate + ADP + Hydrogen ion Adenosyl cobinamide phosphate + Guanosine triphosphate + Hydrogen ion > Adenosylcobinamide-GDP + Pyrophosphate