2.02015-09-08 17:48:43 -06002015-09-08 17:48:43 -0600ECMDB24049M2MDB006166Caproic acidCaproateC6H12O2116.1583116.083729628hexanoic acidhexanoic acidCCCCCC(O)=OInChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)FUZZWVXGSFPDMH-UHFFFAOYSA-Nlogp1.88logs-1.08solubility9.72e+00 g/llogp1.81pka_strongest_acidic5.09iupachexanoic acidaverage_mass116.1583mono_mass116.083729628smilesCCCCCC(O)=OformulaC6H12O2inchiInChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)inchikeyFUZZWVXGSFPDMH-UHFFFAOYSA-Npolar_surface_area37.3refractivity31.07polarizability13.27rotatable_bond_count4acceptor_count2donor_count1physiological_charge-1formal_charge0fatty 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 thiolasePW001019MetabolicSpecdb::CMs909Specdb::CMs3145Specdb::CMs29460Specdb::CMs31164Specdb::CMs37604Specdb::CMs130899Specdb::CMs138633Specdb::CMs1065143Specdb::EiMs795Specdb::NmrOneD1409Specdb::NmrOneD2245Specdb::NmrOneD2940Specdb::NmrOneD5037Specdb::NmrOneD5038Specdb::NmrOneD7022Specdb::NmrOneD7023Specdb::NmrOneD7024Specdb::NmrOneD7025Specdb::NmrOneD7026Specdb::NmrOneD7027Specdb::NmrOneD7028Specdb::NmrOneD7029Specdb::NmrOneD7030Specdb::NmrOneD7031Specdb::NmrOneD7032Specdb::NmrOneD7033Specdb::NmrOneD7034Specdb::NmrOneD7035Specdb::NmrOneD7036Specdb::NmrOneD7037Specdb::NmrOneD7038Specdb::NmrOneD7039Specdb::NmrOneD7040Specdb::NmrOneD7041Specdb::MsMs755Specdb::MsMs756Specdb::MsMs757Specdb::MsMs4182Specdb::MsMs4183Specdb::MsMs4184Specdb::MsMs4185Specdb::MsMs4186Specdb::MsMs179577Specdb::MsMs179578Specdb::MsMs179579Specdb::MsMs181908Specdb::MsMs181909Specdb::MsMs181910Specdb::MsMs437415Specdb::MsMs437416Specdb::MsMs437417Specdb::MsMs437418Specdb::MsMs438697Specdb::MsMs2227615Specdb::MsMs2316623Specdb::MsMs2316624Specdb::MsMs2316625Specdb::MsMs2621960Specdb::MsMs2621961Specdb::NmrTwoD1353Short-chain-fatty-acid--CoA ligaseP38135FADK_ECOLIfadKhttp://ecmdb.ca/proteins/P38135.xmlAdenosine triphosphate + Coenzyme A + Caproic acid > Adenosine monophosphate + Hexanyl-CoAPW_R003760