2.02012-08-09 09:16:16 -06002015-09-13 12:56:16 -0600ECMDB21443M2MDB001838Vaccenic acidVaccenic acid is an unsaturated 18 chain fatty acid (18:1n7) is present at about 25% of the concentration of 18:1n9 in most phospholipids. A notable exception is the phospholipid cardiolipin, which often contains as much 18:1n7 as 18:1n9. (11Z)-Octadecenoate(11Z)-Octadecenoic acid(Z)-Octadec-11-enoate(Z)-Octadec-11-enoic acid11-Octadecenoate11-Octadecenoic acid11Z-octadecenoate11Z-octadecenoic acid18:1 trans-11.cis-VaccenateTrans-11-octadecenoateTrans-11-octadecenoic acidVaccenateC18H34O2282.4614282.255880332(11E)-octadec-11-enoic acidtrans-vaccenic acid693-72-1CCCCCC\C=C/CCCCCCCCCC(O)=OInChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-UWHZIFQPPBDJPM-FPLPWBNLSA-NSolidMembranelogp7.67logs-6.36solubility1.23e-04 g/lmelting_point44 oClogp6.78pka_strongest_acidic4.95iupac(11E)-octadec-11-enoic acidaverage_mass282.4614mono_mass282.255880332smilesCCCCCC\C=C/CCCCCCCCCC(O)=OformulaC18H34O2inchiInChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-inchikeyUWHZIFQPPBDJPM-FPLPWBNLSA-Npolar_surface_area37.3refractivity87.4polarizability37.62rotatable_bond_count15acceptor_count2donor_count1physiological_charge-1formal_charge0Fatty acid metabolismThis pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized.
The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterasePW000796ec00071Metabolicinner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786MetabolicSpecdb::CMs168436Specdb::EiMs1994Specdb::NmrOneD5185Specdb::NmrOneD166378Specdb::NmrOneD166664Specdb::NmrOneD342528Specdb::NmrOneD342529Specdb::NmrOneD342530Specdb::NmrOneD342531Specdb::NmrOneD342532Specdb::NmrOneD342533Specdb::NmrOneD342534Specdb::NmrOneD342535Specdb::NmrOneD342536Specdb::NmrOneD342537Specdb::NmrOneD342538Specdb::NmrOneD342539Specdb::NmrOneD342540Specdb::NmrOneD342541Specdb::NmrOneD342542Specdb::NmrOneD342543Specdb::NmrOneD342544Specdb::NmrOneD342545Specdb::NmrOneD342546Specdb::NmrOneD342547Specdb::MsMs1218150Specdb::MsMs1218151Specdb::MsMs1218152Specdb::MsMs1234045Specdb::MsMs1234046Specdb::MsMs1234047Specdb::MsMs1349542Specdb::MsMs1349543Specdb::MsMs1349544Specdb::MsMs2226267Specdb::MsMs2228664Specdb::MsMs2230763Specdb::MsMs2795483Specdb::MsMs2795484Specdb::MsMs2795485Specdb::MsMs2886692Specdb::MsMs2886693Specdb::MsMs2886694Specdb::NmrTwoD2022HMDB0323152827604445888C0836728727VCAVaccenic acidvan 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. Villanova University: U.S.ASchatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68.3372640http://hmdb.ca/system/metabolites/msds/000/002/814/original/HMDB03231.pdf?1358462028Malonyl CoA-acyl carrier protein transacylaseP0AAI9FABD_ECOLIfabDhttp://ecmdb.ca/proteins/P0AAI9.xmlAcyl-CoA thioesterase IP0ADA1TESA_ECOLItesAhttp://ecmdb.ca/proteins/P0ADA1.xmlBifunctional protein aasP31119AAS_ECOLIaashttp://ecmdb.ca/proteins/P31119.xmlLong-chain-fatty-acid--CoA ligaseP69451LCFA_ECOLIfadDhttp://ecmdb.ca/proteins/P69451.xmlAcyl carrier proteinP0A6A8ACP_ECOLIacpPhttp://ecmdb.ca/proteins/P0A6A8.xml a cis-vaccenoyl-[acp] + Water > Hydrogen ion + a holo-[acyl-carrier protein] + Vaccenic acidPW_R002782