2.0 2012-05-31 09:55:45 -0600 2015-09-13 12:56:05 -0600 ECMDB00039 M2MDB000011 Butyric acid Butyric 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-Butanoate 1-Butanoic acid 1-Butyrate 1-Butyric acid 1-Propanecarboxylate 1-Propanecarboxylic acid Butanate Butanic acid Butanoate Butanoic acid Buttersaeure Butyrate Butyric acid Ethylacetate Ethylacetic acid Honey robber Kyselina maselna N-Butanoate N-Butanoic acid N-Butyrate N-Butyric acid Propanecarboxylate Propanecarboxylic acid Propylformate Propylformic acid C4H8O2 88.1051 88.0524295 butanoic acid butyric acid 107-92-6 CCCC(O)=O InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) FERIUCNNQQJTOY-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp 0.78 ALOGPS logs 0.43 ALOGPS solubility 2.39e+02 g/l ALOGPS melting_point -5.7 oC logp 0.92 ChemAxon pka_strongest_acidic 4.91 ChemAxon iupac butanoic acid ChemAxon average_mass 88.1051 ChemAxon mono_mass 88.0524295 ChemAxon smiles CCCC(O)=O ChemAxon formula C4H8O2 ChemAxon inchi InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) ChemAxon inchikey FERIUCNNQQJTOY-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 21.87 ChemAxon polarizability 9.22 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Butanoate metabolism ec00650 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::CMs 3459 Specdb::CMs 27166 Specdb::CMs 29453 Specdb::CMs 37261 Specdb::CMs 99521 Specdb::CMs 99522 Specdb::CMs 171081 Specdb::CMs 1047401 Specdb::EiMs 1145 Specdb::NmrOneD 1047 Specdb::NmrOneD 1124 Specdb::NmrOneD 2112 Specdb::NmrOneD 2805 Specdb::NmrOneD 5025 Specdb::NmrOneD 5026 Specdb::MsMs 66 Specdb::MsMs 67 Specdb::MsMs 68 Specdb::MsMs 2630 Specdb::MsMs 2631 Specdb::MsMs 2632 Specdb::MsMs 2633 Specdb::MsMs 2634 Specdb::MsMs 19868 Specdb::MsMs 19869 Specdb::MsMs 19870 Specdb::MsMs 21419 Specdb::MsMs 21420 Specdb::MsMs 21421 Specdb::MsMs 437337 Specdb::MsMs 437338 Specdb::MsMs 437339 Specdb::MsMs 2464911 Specdb::MsMs 2464912 Specdb::MsMs 2464913 Specdb::MsMs 2501321 Specdb::MsMs 2501322 Specdb::MsMs 2501323 Specdb::NmrTwoD 1105 HMDB00039 264 259 C00246 30772 BUTYRIC_ACID BUA Butyric_acid Keseler, I. 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(2008), 6pp. http://hmdb.ca/system/metabolites/msds/000/000/028/original/HMDB00039.pdf?1358893684 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 Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Short-chain fatty acids transporter P76460 ATOE_ECOLI atoE http://ecmdb.ca/proteins/P76460.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Acetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoA Butanoyl-CoA + Acetic acid <> Butyric acid + Acetyl-CoA R01179 Butyric acid + Coenzyme A + Adenosine triphosphate > Adenosine triphosphate + Butyryl-CoA + Butyryl-CoA PW_R003758