2.0 2012-05-31 13:45:00 -0600 2015-09-17 15:41:08 -0600 ECMDB01088 M2MDB000250 Butyryl-CoA Butyryl-CoA is a member of the chemical class known as Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. Butyryl-coenzyme A (or butyryl-CoA) is the coenzyme A-activated form of butyric acid. (WikiPedia) Butanoyl-CoA Butanoyl-Coenzyme A Butyryl-CoA Butyryl-coenzyme A C25H42N7O17P3S 837.624 837.157073179 (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)-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (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]-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid 2140-48-9 CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40) CRFNGMNYKDXRTN-UHFFFAOYSA-N Cytosol logp -0.22 ALOGPS logs -2.32 ALOGPS solubility 4.01e+00 g/l ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 6.46 ChemAxon iupac (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)-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid ChemAxon average_mass 837.624 ChemAxon mono_mass 837.157073179 ChemAxon smiles CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N ChemAxon formula C25H42N7O17P3S ChemAxon inchi InChI=1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40) ChemAxon inchikey CRFNGMNYKDXRTN-UHFFFAOYSA-N ChemAxon polar_surface_area 370.61 ChemAxon refractivity 182.48 ChemAxon polarizability 75.14 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 19 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Valine, leucine and isoleucine degradation ec00280 fatty acid oxidation (Butanoate) Although enzymes of the pathway handle both short and long chain fatty acids, it is the long chain compounds that induce the enzymes of the pathway . Each turn of the cycle removes two carbon atoms until only two or three remain. When even-numbered fatty acids are broken down, a two-carbon compound remains, acetyl-CoA. When odd number fatty acids are broken down, a three-carbon residue results, propionylCoA. Unsaturated fatty acids, with cis double bonds located at odd-numbered carbon atoms, enter the main pathway of saturated fatty acid degradation by converting related metabolites of cis configuration and D stereoisomers, derived from breakdown of unsaturated fatty acids, to the trans- or L isomers of saturated fatty acid breakdown by an isomerase and an epimerase, respectively. When cis double bonds are located at even-numbered carbon atoms, such as linoleic acid (cis,cis(9,12)-octadecadienoic acid), after the fatty acid is degraded to the ten carbon stage an extra step is required to deal with the resulting compound, trans,δ(2)-cis,δ(4)decadienoyl-CoA. The enzyme 2,4-dienoyl-CoA reductase, converts this to trans,δ(2)decenoyl-CoA which enters the normal cycle at the point of the isomerase. The order of the reaction is as follows: a 2,3,4 saturated fatty acid is transformed into a 2,3,4 saturated fatty acyl CoA through a Long and short chain fatty acid CoA ligase. The 2,3,4 saturated fatty acyl CoA is then transformed into a trans 2 enoyl CoA. This enoyl can also be produced from a cis 3 enoyl CoA through a fatty acid oxidation protein complex. The trans 2 enoyl is transformed into a 3s 3 hydroxyacyl CoA through a 2,3 dehydroadipyl CoA hydratase. This same enzyme turns the product into a 3-oxoacyl-CoA. This is followed by the last step in the reaction when the oxoacyl-coa is turn into an acetyl coa+ a 2,3,4 saturated fatty acyl CoA through a 3-ketoacyl-CoA thiolase PW001017 Metabolic Specdb::MsMs 34760 Specdb::MsMs 34761 Specdb::MsMs 34762 Specdb::MsMs 3608464 Specdb::MsMs 3608465 Specdb::MsMs 3608466 Specdb::MsMs 28202 Specdb::MsMs 28203 Specdb::MsMs 28204 Specdb::MsMs 3609715 Specdb::MsMs 3609716 Specdb::MsMs 3609717 HMDB01088 109043 C00136 15479 BUTYRYL-COA Butyryl-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 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 Aldehyde-alcohol dehydrogenase P0A9Q7 ADHE_ECOLI adhE http://ecmdb.ca/proteins/P0A9Q7.xml 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml Acetate CoA-transferase subunit alpha P76458 ATOD_ECOLI atoD http://ecmdb.ca/proteins/P76458.xml Acetate CoA-transferase subunit beta P76459 ATOA_ECOLI atoA http://ecmdb.ca/proteins/P76459.xml Acetyl-CoA acetyltransferase P76461 ATOB_ECOLI atoB http://ecmdb.ca/proteins/P76461.xml 3-ketoacyl-CoA thiolase_ P76503 FADI_ECOLI fadI http://ecmdb.ca/proteins/P76503.xml Acetaldehyde dehydrogenase P77580 ACDH_ECOLI mhpF http://ecmdb.ca/proteins/P77580.xml Probable acetyl-CoA acetyltransferase Q46939 YQEF_ECOLI yqeF http://ecmdb.ca/proteins/Q46939.xml Acyl-coenzyme A dehydrogenase Q47146 FADE_ECOLI fadE http://ecmdb.ca/proteins/Q47146.xml Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Acetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoA Acetyl-CoA + Butyryl-CoA <> 3-Oxohexanoyl-CoA + Coenzyme A Butyryl-CoA + FAD <> Crotonoyl-CoA + FADH2 Butyryl-CoA + electron-transfer flavoprotein + Butyryl-CoA <> Crotonoyl-CoA + Reduced electron-transfer flavoprotein PW_R002480 Acetyl-CoA + Butyryl-CoA + Butyryl-CoA > 3-Oxohexanoyl-CoA + Coenzyme A PW_R002748 Butyric acid + Coenzyme A + Adenosine triphosphate > Adenosine triphosphate + Butyryl-CoA + Butyryl-CoA PW_R003758