2.0 2012-05-31 13:55:15 -0600 2015-06-03 15:17:57 -0600 ECMDB02054 M2MDB000433 Tiglyl-CoA Tiglyl-CoA is a metabolite in the degradation of isoleucine to propionic acid pathway. It is a substrate of enoyl-CoA hydratase-isomerase [EC:4.2.1.17] and converted to (2S,3S)-3-Hydroxy-2-methylbutanoyl-CoA. (E)-2-Methylcrotonoyl-CoA (E)-2-Methylcrotonoyl-Coenzyme A 2-Methylbut-2-enoyl-CoA 2-Methylbut-2-enoyl-Coenzyme A 2-Methylcrotanoyl-CoA 2-Methylcrotanoyl-Coenzyme A 2-Methylcrotonoyl-CoA 2-Methylcrotonoyl-Coenzyme A 2-Methylcrotonyl-CoA 2-Methylcrotonyl-Coenzyme A Methylcrotonoyl-CoA Methylcrotonoyl-Coenzyme A Methylcrotonyl-CoA Methylcrotonyl-Coenzyme A Tigloyl-CoA Tigloyl-Coenzyme A Tiglyl-CoA Tiglyl-coenzyme A Trans-2-Methylbut-2-enoyl-CoA Trans-2-Methylbut-2-enoyl-Coenzyme A C26H42N7O17P3S 849.635 849.157073179 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid C\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20?,24-/m1/s1 PMWATMXOQQZNBX-APMDNKNFSA-N Solid Cytoplasm Periplasm logp 0.12 ALOGPS logs -2.19 ALOGPS solubility 5.48e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 849.635 ChemAxon mono_mass 849.157073179 ChemAxon smiles C\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 ChemAxon formula C26H42N7O17P3S ChemAxon inchi InChI=1S/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20?,24-/m1/s1 ChemAxon inchikey PMWATMXOQQZNBX-APMDNKNFSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 186.89 ChemAxon polarizability 76.74 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Valine, leucine and isoleucine degradation ec00280 Specdb::EiMs 3988 Specdb::NmrOneD 270338 Specdb::NmrOneD 270339 Specdb::NmrOneD 270340 Specdb::NmrOneD 270341 Specdb::NmrOneD 270342 Specdb::NmrOneD 270343 Specdb::NmrOneD 270344 Specdb::NmrOneD 270345 Specdb::NmrOneD 270346 Specdb::NmrOneD 270347 Specdb::NmrOneD 270348 Specdb::NmrOneD 270349 Specdb::NmrOneD 270350 Specdb::NmrOneD 270351 Specdb::NmrOneD 270352 Specdb::NmrOneD 270353 Specdb::NmrOneD 270354 Specdb::NmrOneD 270355 Specdb::NmrOneD 270356 Specdb::NmrOneD 270357 Specdb::MsMs 29735 Specdb::MsMs 29736 Specdb::MsMs 29737 Specdb::MsMs 36293 Specdb::MsMs 36294 Specdb::MsMs 36295 HMDB02054 439894 4444187 C03345 15478 TIGLYL-COA Tiglyl-CoA 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 Duran M, Bruinvis L, Ketting D, Kamerling JP, Wadman SK, Schutgens RB: The identification of (E)-2-methylglutaconic acid, a new isoleucine metabolite, in the urine of patients with beta-ketothiolase deficiency, propionic acidaemia and methylmalonic acidaemia. Biomed Mass Spectrom. 1982 Jan;9(1):1-5. 7059658 Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Probable enoyl-CoA hydratase paaF P76082 PAAF_ECOLI paaF http://ecmdb.ca/proteins/P76082.xml Fatty acid oxidation complex subunit alpha_ P77399 FADJ_ECOLI fadJ http://ecmdb.ca/proteins/P77399.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml 2-Methyl-3-hydroxybutyryl-CoA <> Tiglyl-CoA + Water R04204