2.0 2015-09-08 17:48:43 -0600 2015-09-08 17:48:43 -0600 ECMDB24049 M2MDB006166 Caproic acid Caproate C6H12O2 116.1583 116.083729628 hexanoic acid hexanoic acid CCCCCC(O)=O InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) FUZZWVXGSFPDMH-UHFFFAOYSA-N logp 1.88 ALOGPS logs -1.08 ALOGPS solubility 9.72e+00 g/l ALOGPS logp 1.81 ChemAxon pka_strongest_acidic 5.09 ChemAxon iupac hexanoic acid ChemAxon average_mass 116.1583 ChemAxon mono_mass 116.083729628 ChemAxon smiles CCCCCC(O)=O ChemAxon formula C6H12O2 ChemAxon inchi InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) ChemAxon inchikey FUZZWVXGSFPDMH-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 31.07 ChemAxon polarizability 13.27 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon 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::CMs 909 Specdb::CMs 3145 Specdb::CMs 29460 Specdb::CMs 31164 Specdb::CMs 37604 Specdb::CMs 130899 Specdb::CMs 138633 Specdb::CMs 1065143 Specdb::EiMs 795 Specdb::NmrOneD 1409 Specdb::NmrOneD 2245 Specdb::NmrOneD 2940 Specdb::NmrOneD 5037 Specdb::NmrOneD 5038 Specdb::NmrOneD 7022 Specdb::NmrOneD 7023 Specdb::NmrOneD 7024 Specdb::NmrOneD 7025 Specdb::NmrOneD 7026 Specdb::NmrOneD 7027 Specdb::NmrOneD 7028 Specdb::NmrOneD 7029 Specdb::NmrOneD 7030 Specdb::NmrOneD 7031 Specdb::NmrOneD 7032 Specdb::NmrOneD 7033 Specdb::NmrOneD 7034 Specdb::NmrOneD 7035 Specdb::NmrOneD 7036 Specdb::NmrOneD 7037 Specdb::NmrOneD 7038 Specdb::NmrOneD 7039 Specdb::NmrOneD 7040 Specdb::NmrOneD 7041 Specdb::MsMs 755 Specdb::MsMs 756 Specdb::MsMs 757 Specdb::MsMs 4182 Specdb::MsMs 4183 Specdb::MsMs 4184 Specdb::MsMs 4185 Specdb::MsMs 4186 Specdb::MsMs 179577 Specdb::MsMs 179578 Specdb::MsMs 179579 Specdb::MsMs 181908 Specdb::MsMs 181909 Specdb::MsMs 181910 Specdb::MsMs 437415 Specdb::MsMs 437416 Specdb::MsMs 437417 Specdb::MsMs 437418 Specdb::MsMs 438697 Specdb::MsMs 2227615 Specdb::MsMs 2316623 Specdb::MsMs 2316624 Specdb::MsMs 2316625 Specdb::MsMs 2621960 Specdb::MsMs 2621961 Specdb::NmrTwoD 1353 Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Adenosine triphosphate + Coenzyme A + Caproic acid > Adenosine monophosphate + Hexanyl-CoA PW_R003760