2.02012-05-31 09:55:45 -06002015-09-13 12:56:05 -0600ECMDB00039M2MDB000011Butyric acidButyric acid, also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.1-Butanoate1-Butanoic acid1-Butyrate1-Butyric acid1-Propanecarboxylate1-Propanecarboxylic acidButanateButanic acidButanoateButanoic acidButtersaeureButyrateButyric acidEthylacetateEthylacetic acidHoney robberKyselina maselnaN-ButanoateN-Butanoic acidN-ButyrateN-Butyric acidPropanecarboxylatePropanecarboxylic acidPropylformatePropylformic acidC4H8O288.105188.0524295butanoic acidbutyric acid107-92-6CCCC(O)=OInChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)FERIUCNNQQJTOY-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmlogp0.78logs0.43solubility2.39e+02 g/lmelting_point-5.7 oClogp0.92pka_strongest_acidic4.91iupacbutanoic acidaverage_mass88.1051mono_mass88.0524295smilesCCCC(O)=OformulaC4H8O2inchiInChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)inchikeyFERIUCNNQQJTOY-UHFFFAOYSA-Npolar_surface_area37.3refractivity21.87polarizability9.22rotatable_bond_count2acceptor_count2donor_count1physiological_charge-1formal_charge0Butanoate metabolismec00650fatty 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 thiolasePW001017MetabolicSpecdb::CMs3459Specdb::CMs27166Specdb::CMs29453Specdb::CMs37261Specdb::CMs99521Specdb::CMs99522Specdb::CMs171081Specdb::CMs1047401Specdb::EiMs1145Specdb::NmrOneD1047Specdb::NmrOneD1124Specdb::NmrOneD2112Specdb::NmrOneD2805Specdb::NmrOneD5025Specdb::NmrOneD5026Specdb::MsMs66Specdb::MsMs67Specdb::MsMs68Specdb::MsMs2630Specdb::MsMs2631Specdb::MsMs2632Specdb::MsMs2633Specdb::MsMs2634Specdb::MsMs19868Specdb::MsMs19869Specdb::MsMs19870Specdb::MsMs21419Specdb::MsMs21420Specdb::MsMs21421Specdb::MsMs437337Specdb::MsMs437338Specdb::MsMs437339Specdb::MsMs2464911Specdb::MsMs2464912Specdb::MsMs2464913Specdb::MsMs2501321Specdb::MsMs2501322Specdb::MsMs2501323Specdb::NmrTwoD1105HMDB00039264259C0024630772BUTYRIC_ACIDBUAButyric_acidKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. 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(2008), 6pp. http://hmdb.ca/system/metabolites/msds/000/000/028/original/HMDB00039.pdf?1358893684Acetate CoA-transferase subunit alphaP76458ATOD_ECOLIatoDhttp://ecmdb.ca/proteins/P76458.xmlAcetate CoA-transferase subunit betaP76459ATOA_ECOLIatoAhttp://ecmdb.ca/proteins/P76459.xmlShort-chain-fatty-acid--CoA ligaseP38135FADK_ECOLIfadKhttp://ecmdb.ca/proteins/P38135.xmlShort-chain fatty acids transporterP76460ATOE_ECOLIatoEhttp://ecmdb.ca/proteins/P76460.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAcetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoAButanoyl-CoA + Acetic acid <> Butyric acid + Acetyl-CoAR01179Butyric acid + Coenzyme A + Adenosine triphosphate > Adenosine triphosphate + Butyryl-CoA + Butyryl-CoAPW_R003758