2.0 2012-05-31 14:01:08 -0600 2015-06-03 15:54:34 -0600 ECMDB03943 M2MDB000539 3-Oxohexanoyl-CoA 3-Oxohexanoyl-CoA is an intermediate in Fatty acid elongation. 3-Oxohexanoyl-CoA is the 3rd to last step in the synthesis of Hexanoyl-CoA and is converted from Butanoyl-CoA via the enzyme acetyl-CoA acyltransferase 2 (EC 2.3.1.16). It is then converted to (S)-Hydroxyhexanoyl-CoA via the 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35). &beta;-hexanoyl-CoA 3-Ketohexanoyl CoA. 3-Ketohexanoyl Coenzyme A. 3-Ketohexanoyl-CoA 3-Oxohexanoyl-CoA 3-Oxohexanoyl-Coenzyme A b-Hexanoyl-CoA Beta-Hexanoyl-CoA Ketohexanoyl-CoA Ketohexanoyl-Coenzyme A Ketohexanoyl-coenzyme-A β-Hexanoyl-CoA C27H44N7O18P3S 879.661 879.167637865 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexanoyl)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-[(3-oxohexanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid 19774-86-8 CCCC(=O)CC(=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/C27H44N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-14,16,20-22,26,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t16-,20-,21-,22?,26-/m1/s1 NFOYYXQAVVYWKV-ZOGSZLKASA-N Solid Cytosol logp -0.04 ALOGPS logs -2.41 ALOGPS solubility 3.43e+00 g/l ALOGPS logp -5.6 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 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-[(3-oxohexanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 879.661 ChemAxon mono_mass 879.167637865 ChemAxon smiles CCCC(=O)CC(=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 C27H44N7O18P3S ChemAxon inchi InChI=1S/C27H44N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-14,16,20-22,26,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t16-,20-,21-,22?,26-/m1/s1 ChemAxon inchikey NFOYYXQAVVYWKV-ZOGSZLKASA-N ChemAxon polar_surface_area 380.7 ChemAxon refractivity 191.33 ChemAxon polarizability 77.82 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Fatty acid metabolism This pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized. The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterase PW000796 ec00071 Metabolic fatty acid oxidation (hexanoate) 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 PW001019 Metabolic Specdb::NmrOneD 35082 Specdb::NmrOneD 35083 Specdb::NmrOneD 35084 Specdb::NmrOneD 35085 Specdb::NmrOneD 35086 Specdb::NmrOneD 35087 Specdb::NmrOneD 35088 Specdb::NmrOneD 35089 Specdb::NmrOneD 35090 Specdb::NmrOneD 35091 Specdb::NmrOneD 35092 Specdb::NmrOneD 35093 Specdb::NmrOneD 35094 Specdb::NmrOneD 35095 Specdb::NmrOneD 35096 Specdb::NmrOneD 35097 Specdb::NmrOneD 35098 Specdb::NmrOneD 35099 Specdb::NmrOneD 35100 Specdb::NmrOneD 35101 Specdb::MsMs 24365 Specdb::MsMs 24366 Specdb::MsMs 24367 Specdb::MsMs 30923 Specdb::MsMs 30924 Specdb::MsMs 30925 Specdb::MsMs 2377801 Specdb::MsMs 2377802 Specdb::MsMs 2377803 Specdb::MsMs 2561706 Specdb::MsMs 2561707 Specdb::MsMs 2561708 HMDB03943 440610 389508 C05269 27648 K-HEXANOYL-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 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml 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 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 Fatty acid oxidation complex subunit alpha_ P77399 FADJ_ECOLI fadJ http://ecmdb.ca/proteins/P77399.xml Probable acetyl-CoA acetyltransferase Q46939 YQEF_ECOLI yqeF http://ecmdb.ca/proteins/Q46939.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Acetyl-CoA + Butyryl-CoA <> 3-Oxohexanoyl-CoA + Coenzyme A 3-Oxohexanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxyhexanoyl-CoA + NAD R04748 Acetyl-CoA + Butanoyl-CoA <> Coenzyme A + 3-Oxohexanoyl-CoA R01177 (S)-Hydroxyhexanoyl-CoA + NAD <> 3-Oxohexanoyl-CoA + NADH + Hydrogen ion R04748 (S)-Hydroxyhexanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxohexanoyl-CoA PW_R003779 3-Oxohexanoyl-CoA + Coenzyme A > Acetyl-CoA + Octanoyl-CoA + Octanoyl-CoA PW_R003780 (S)-Hydroxyhexanoyl-CoA + NAD <> 3-Oxohexanoyl-CoA + NADH + Hydrogen ion PW_R002479 Acetyl-CoA + Butyryl-CoA + Butyryl-CoA > 3-Oxohexanoyl-CoA + Coenzyme A PW_R002748