2.0 2012-10-10 12:20:15 -0600 2015-06-03 17:26:04 -0600 ECMDB23169 M2MDB003559 3'-dephospho-CoA 3'-dephospho-CoA is a substrate for the enzyme 2-(5''-triphosphoribosyl)-3'-dephosphocoenzyme-A synthase (CitG), which catalyzes the formation of 2-(5''-triphosphoribosyl)-3'-dephosphocoenzyme-A, the precursor of the prosthetic group of the holo-acyl carrier protein (gamma chain) of citrate lyase, from ATP and dephospho-CoA. The reaction is: ATP + 3-dephospho-CoA = 2'-(5-triphosphoribosyl)-3'-dephospho-CoA + adenine. The gamma-subunit of citrate lyase (EC 4.1.3.6) contains the prosthetic group 2'-(5"-phosphoribosyl)-3'-dephospho-CoA and serves as an acyl carrier protein (ACP) in E. coli. It has been shown that in Escherichia coli the proteins CitG and CitX are essential for holo-ACP synthesis and that CitG catalyzes the conversion of ATP and dephospho-CoA to adenine and 2'-(5"-triphosphoribosyl)-3'-dephospho-CoA [PMID:11042274] (2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulfanylethyl)aminopropyl}amino)butyl dihydrogen diphosphate (non-p referred name) (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulfanylethyl)aminopropyl}amino)butyl dihydrogen diphosphoric acid (non-p referred name) (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulphanylethyl)aminopropyl}amino)butyl dihydrogen diphosphate (non-p referred name) (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulphanylethyl)aminopropyl}amino)butyl dihydrogen diphosphoric acid (non-p referred name) (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulfanylethylamino)propylaminobutyl hydrogen phosphate (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulfanylethylamino)propylaminobutyl hydrogen phosphoric acid (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulphanylethylamino)propylaminobutyl hydrogen phosphate (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulphanylethylamino)propylaminobutyl hydrogen phosphoric acid 3'-Dephospho-CoA 3'-dephospho-Coenzyme A 3'-O-dephosphono-CoA 3'-O-dephosphono-Coenzyme A 3-dephospho-CoA Dephospho-CoA Dephospho-Coenzyme A Dephosphocoenzyme A C21H35N7O13P2S 687.554 687.148877955 [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid 3'-dephospho-coa 3633-59-8 CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16+,20-/m1/s1 KDTSHFARGAKYJN-IBOSZNHHSA-N Solid Cytoplasm lysosome logp -0.98 ALOGPS logs -2.43 ALOGPS solubility 2.56e+00 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid ChemAxon average_mass 687.554 ChemAxon mono_mass 687.148877955 ChemAxon smiles CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS ChemAxon formula C21H35N7O13P2S ChemAxon inchi InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16+,20-/m1/s1 ChemAxon inchikey KDTSHFARGAKYJN-IBOSZNHHSA-N ChemAxon polar_surface_area 300.03 ChemAxon refractivity 151.87 ChemAxon polarizability 63.64 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 14 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 733569 Specdb::CMs 733570 Specdb::CMs 733571 Specdb::CMs 733572 Specdb::CMs 733573 Specdb::CMs 733574 Specdb::CMs 733575 Specdb::CMs 733576 Specdb::CMs 733577 Specdb::CMs 733578 Specdb::CMs 733579 Specdb::CMs 733580 Specdb::CMs 733581 Specdb::CMs 733582 Specdb::CMs 733583 Specdb::CMs 733584 Specdb::CMs 733585 Specdb::CMs 733586 Specdb::CMs 733587 Specdb::CMs 733588 Specdb::CMs 733589 Specdb::CMs 733590 Specdb::CMs 733591 Specdb::CMs 733592 Specdb::CMs 733593 Specdb::NmrOneD 87912 Specdb::NmrOneD 87913 Specdb::NmrOneD 87914 Specdb::NmrOneD 87915 Specdb::NmrOneD 87916 Specdb::NmrOneD 87917 Specdb::NmrOneD 87918 Specdb::NmrOneD 87919 Specdb::NmrOneD 87920 Specdb::NmrOneD 87921 Specdb::NmrOneD 87922 Specdb::NmrOneD 87923 Specdb::NmrOneD 87924 Specdb::NmrOneD 87925 Specdb::NmrOneD 87926 Specdb::NmrOneD 87927 Specdb::NmrOneD 87928 Specdb::NmrOneD 87929 Specdb::NmrOneD 87930 Specdb::NmrOneD 87931 Specdb::MsMs 23960 Specdb::MsMs 23961 Specdb::MsMs 23962 Specdb::MsMs 30758 Specdb::MsMs 30759 Specdb::MsMs 30760 Specdb::MsMs 2256757 Specdb::MsMs 2257813 Specdb::MsMs 3040333 Specdb::MsMs 3040334 Specdb::MsMs 3040335 Specdb::MsMs 3103175 Specdb::MsMs 3103176 Specdb::MsMs 3103177 HMDB01373 439335 C00882 15468 DEPHOSPHO-COA COD FDB022585 Phosphopantetheine adenylyltransferase P0A6I6 COAD_ECOLI coaD http://ecmdb.ca/proteins/P0A6I6.xml Dephospho-CoA kinase P0A6I9 COAE_ECOLI coaE http://ecmdb.ca/proteins/P0A6I9.xml Adenosine triphosphate + pantotheine 4'-phosphate > Pyrophosphate + 3'-dephospho-CoA Adenosine triphosphate + 3'-dephospho-CoA > ADP + CoA