2.0 2012-05-31 10:26:52 -0600 2015-10-02 02:25:50 -0600 ECMDB00482 M2MDB000140 Caprylic acid Caprylic acid belongs to the class of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. (inferred from compound structure). Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. (WikiPedia). Caprylic acid is an intermediate in lipoate biosynthesis and incorporation II in E. coli. It is a substrate for lipoate-protein ligase A which catalyzes the chemical reaction a [lipoyl-carrier protein]-L-lysine + caprylic acid + ATP -> a [lipoyl-carrier protein] N6-octanoyl-L-lysine + AMP + diphosphate + H+. It is also a substrate for acyl-ACP synthetase in the reaction caprylic acid + a holo-[acyl-carrier protein] + ATP → an octanoyl-[acp] + AMP + diphosphate (EcoCyc compound: CPD-195). 1-Heptanecarboxylate 1-Heptanecarboxylic acid C-8 Acid Caprylate Caprylic acid Capryloate Capryloic acid Emery 657 Kortacid 0899 Lunac 8-95 Lunac 8-98 N-Caprylate N-Caprylic acid N-Octanoate N-Octanoic acid N-Octate N-Octic acid N-Octoate N-Octoic acid N-Octylate N-Octylic acid Neo-Fat 8 Neo-Fat 8S Octanoate Octanoate (N-C8:0) Octanoic acid Octanoic acid (N-C8:0) Octoate Octoic acid Octylate Octylic acid Prifac 2901 C8H16O2 144.2114 144.115029756 octanoic acid caprylic acid 124-07-2 CCCCCCCC(O)=O InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) WWZKQHOCKIZLMA-UHFFFAOYSA-N Liquid Membrane logp 2.92 ALOGPS logs -2.20 ALOGPS solubility 9.07e-01 g/l ALOGPS melting_point 16.5 oC logp 2.7 ChemAxon pka_strongest_acidic 5.19 ChemAxon iupac octanoic acid ChemAxon average_mass 144.2114 ChemAxon mono_mass 144.115029756 ChemAxon smiles CCCCCCCC(O)=O ChemAxon formula C8H16O2 ChemAxon inchi InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) ChemAxon inchikey WWZKQHOCKIZLMA-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 40.28 ChemAxon polarizability 17.4 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Fatty acid biosynthesis The fatty acid biosynthesis starts from acetyl-CoA reacting either with a holo-[acp] through a 3-oxoacyl-[acp] synthase 3 resulting in an acetyl-[acp] or react with hydrogen carbonate through an ATP driven acetyl-CoA carboxylase resulting in a malonyl-CoA. Malonyl-CoA reacts with a holo-acp] through a malonyl-CoA-ACP transacylase resulting in a malonyl-[acp]. This compound can react with a KASI protein resulting in an acetyl-[acp]. A malonyl-[acp] can also react with an acetyl-[acp] through KASI and KASII or with acetyl-CoA through a beta-ketoacyl-ACP synthase to produce an acetoacetyl-[acp]. An acetoacetyl-[acp] is also known as a 3-oxoacyl-[acp]. A 3-oxoacyl-[acp] is reduced through a NDPH mediated 3-oxoacyl-[acp] reductase resulting in a (3R)-3-hydroxyacyl-[acp] (R3 hydroxydecanoyl-[acp]) which can either join the fatty acid metabolism, be dehydrated by an 3R-hydroxymyristoyl-[acp] dehydratase to produce a trans-2-enoyl-[acp] or be dehydrated by a hydroxydecanoyl-[acp] to produce a trans-delta2 decenoyl-[acp]. Trans-2-enoyl-[acp] is reduced by a NADH driven enoyl-[acp] reductase resulting in a 2,3,4-saturated fatty acyl-[acp]. This product then reacts with malonyl-[acp] through KASI and KASII resulting in a holo-acyl carrier protein and a 3- oxoacyl-[acp]. Trans-delta2 decenoyl-[acp] reacts with a 3-hydroxydecanoyl-[acp] dehydrase producing a cis-delta 3-decenoyl-ACP. This product then reacts with KASI to produce a 3-oxo-cis-delta5-dodecenoyl-[acp], which in turn is reduced by a NADPH driven 3-oxoacyl-[acp] resulting in a 3R-hydroxy cis delta5-dodecenoyl-acp. This product is dehydrated by a (3R)-hydroxymyristoyl-[acp] dehydratase resulting in a trans-delta 3- cis-delta 5-dodecenoyl-[acp] which in turn is reduced by a NADH driven enoyl-[acp] reductase resulting in a cis-delta5-dodecenoyl-acp which goes into fatty acid metabolism PW000900 ec00061 Metabolic Lipoic acid metabolism Lipoic acid metabolism starts with caprylic acid being introduced into the cytoplasm however no transporter has been identified yet. Once caprylic acid is in the cytoplasm, it can either reacts with a holo-acp, through an ATP driven 2-acylglycerophosphoethanolamine acyltransferase / acyl-ACP synthetase resulting in pyrophosphate, AMP and octanoyl-[acp]. The latter compound can also be obtained from palmitate biosynthesis. Octanoyl-acp interacts with a lipoyl-carrier protein L-lysine through a Octanoyltransferase resulting in a hydrogen ion, a holo-acyl-acp, and a protein N6-0octanoyl) lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. Caprylic acid can also interact with ATP and a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting in a amp, pyrophosphate, hydrogen ion, protein N6-(octanoyl)lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. R-lipoic acid can be absorbed from the environment, as seen in studies by Morris TW. In this pathway the lipoyl-protein ligase LplA utilizes pre-existing lipoate that has been imported from outside the cell, and thus catalyzes a salvage pathway. Lipoic acid interacts with ATP and hydrogen ion through a lipoyl-protein ligase A, resulting in a pyrophosphate and a Lipoyl-AMP (lipoyl-adenylate). This compound then interacts with a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting a AMP, a hydrogen ion and a Protein N6-(lipoyl) lysine. It has been suggested that the conversion of octanoylated-domains to lipoylated ones described in this pathway may be a type of a repair pathway, activated only if the other lipoate biosynthetic pathways are malfunctioning . PW000770 ec00785 Metabolic fatty acid oxidation (octanoate) 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 PW001022 Metabolic lipoate biosynthesis and incorporation II PWY0-1275 Specdb::CMs 557 Specdb::CMs 991 Specdb::CMs 2501 Specdb::CMs 29469 Specdb::CMs 30118 Specdb::CMs 30644 Specdb::CMs 31152 Specdb::CMs 31993 Specdb::CMs 37560 Specdb::CMs 162715 Specdb::CMs 1063271 Specdb::EiMs 896 Specdb::NmrOneD 1389 Specdb::NmrOneD 2206 Specdb::NmrOneD 2900 Specdb::NmrOneD 4932 Specdb::NmrOneD 4933 Specdb::MsMs 698 Specdb::MsMs 699 Specdb::MsMs 700 Specdb::MsMs 4096 Specdb::MsMs 4097 Specdb::MsMs 4098 Specdb::MsMs 178293 Specdb::MsMs 178294 Specdb::MsMs 178295 Specdb::MsMs 180609 Specdb::MsMs 180610 Specdb::MsMs 180611 Specdb::MsMs 374162 Specdb::MsMs 437424 Specdb::MsMs 437425 Specdb::MsMs 438695 Specdb::MsMs 2244259 Specdb::MsMs 2245853 Specdb::MsMs 2246424 Specdb::MsMs 2697189 Specdb::MsMs 2697190 Specdb::MsMs 2697191 Specdb::MsMs 2981813 Specdb::MsMs 2981814 Specdb::MsMs 2981815 Specdb::NmrTwoD 1333 HMDB00482 370 C06423 28837 CPD-195 OCA Caprylic acid Keseler, I. 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Kokai Tokkyo Koho (1983), 4 pp. http://hmdb.ca/system/metabolites/msds/000/000/401/original/HMDB00482.pdf?1358463203 Acyl carrier protein phosphodiesterase P21515 ACPH_ECOLI acpH http://ecmdb.ca/proteins/P21515.xml Bifunctional protein aas P31119 AAS_ECOLI aas http://ecmdb.ca/proteins/P31119.xml Lipoate-protein ligase A P32099 LPLA_ECOLI lplA http://ecmdb.ca/proteins/P32099.xml Long-chain-fatty-acid--CoA ligase P69451 LCFA_ECOLI fadD http://ecmdb.ca/proteins/P69451.xml Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Acyl-CoA thioesterase 2 P0AGG2 TESB_ECOLI tesB http://ecmdb.ca/proteins/P0AGG2.xml Acyl carrier protein P0A6A8 ACP_ECOLI acpP http://ecmdb.ca/proteins/P0A6A8.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 Adenosine triphosphate + Coenzyme A + Hydrogen ion + Caprylic acid > Adenosine monophosphate + Hydrogen ion + Octanoyl-CoA + Pyrophosphate acyl carrier protein + Adenosine triphosphate + Caprylic acid > Adenosine monophosphate + Octanoyl-ACP (n-C8:0ACP) + Pyrophosphate Water + Octanoyl-ACP (n-C8:0ACP) > acyl carrier protein + Hydrogen ion + Caprylic acid Water + Octanoyl-CoA > Coenzyme A + Hydrogen ion + Caprylic acid Adenosine triphosphate + Hydrogen ion + Caprylic acid > Adenosine monophosphate + octanoate (protein bound) + Pyrophosphate Caprylic acid + Adenosine triphosphate + a [lipoyl-carrier protein]-L-lysine > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + Protein N6-(octanoyl)lysine PW_R003563 Caprylic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Octanoyl-CoA + Octanoyl-CoA PW_R003763 Caprylic acid + a holo-[acyl-carrier protein] + Adenosine triphosphate > Octanoyl-[acyl-carrier protein] + Adenosine monophosphate + Pyrophosphate PW_R003562