2.0 2012-08-09 09:16:16 -0600 2015-09-13 12:56:16 -0600 ECMDB21443 M2MDB001838 Vaccenic acid Vaccenic 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 acid 11-Octadecenoate 11-Octadecenoic acid 11Z-octadecenoate 11Z-octadecenoic acid 18:1 trans-11. cis-Vaccenate Trans-11-octadecenoate Trans-11-octadecenoic acid Vaccenate C18H34O2 282.4614 282.255880332 (11E)-octadec-11-enoic acid trans-vaccenic acid 693-72-1 CCCCCC\C=C/CCCCCCCCCC(O)=O InChI=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-N Solid Membrane logp 7.67 ALOGPS logs -6.36 ALOGPS solubility 1.23e-04 g/l ALOGPS melting_point 44 oC logp 6.78 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac (11E)-octadec-11-enoic acid ChemAxon average_mass 282.4614 ChemAxon mono_mass 282.255880332 ChemAxon smiles CCCCCC\C=C/CCCCCCCCCC(O)=O ChemAxon formula C18H34O2 ChemAxon inchi InChI=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- ChemAxon inchikey UWHZIFQPPBDJPM-FPLPWBNLSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 87.4 ChemAxon polarizability 37.62 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Fatty acid metabolism This 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 thioesterase PW000796 ec00071 Metabolic inner membrane transport list 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 added PW000786 Metabolic Specdb::CMs 168436 Specdb::EiMs 1994 Specdb::NmrOneD 5185 Specdb::NmrOneD 166378 Specdb::NmrOneD 166664 Specdb::NmrOneD 342528 Specdb::NmrOneD 342529 Specdb::NmrOneD 342530 Specdb::NmrOneD 342531 Specdb::NmrOneD 342532 Specdb::NmrOneD 342533 Specdb::NmrOneD 342534 Specdb::NmrOneD 342535 Specdb::NmrOneD 342536 Specdb::NmrOneD 342537 Specdb::NmrOneD 342538 Specdb::NmrOneD 342539 Specdb::NmrOneD 342540 Specdb::NmrOneD 342541 Specdb::NmrOneD 342542 Specdb::NmrOneD 342543 Specdb::NmrOneD 342544 Specdb::NmrOneD 342545 Specdb::NmrOneD 342546 Specdb::NmrOneD 342547 Specdb::MsMs 1218150 Specdb::MsMs 1218151 Specdb::MsMs 1218152 Specdb::MsMs 1234045 Specdb::MsMs 1234046 Specdb::MsMs 1234047 Specdb::MsMs 1349542 Specdb::MsMs 1349543 Specdb::MsMs 1349544 Specdb::MsMs 2226267 Specdb::MsMs 2228664 Specdb::MsMs 2230763 Specdb::MsMs 2795483 Specdb::MsMs 2795484 Specdb::MsMs 2795485 Specdb::MsMs 2886692 Specdb::MsMs 2886693 Specdb::MsMs 2886694 Specdb::NmrTwoD 2022 HMDB03231 5282760 4445888 C08367 28727 VCA Vaccenic acid van 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. 17765195 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Schatowitz 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. 3372640 http://hmdb.ca/system/metabolites/msds/000/002/814/original/HMDB03231.pdf?1358462028 Malonyl CoA-acyl carrier protein transacylase P0AAI9 FABD_ECOLI fabD http://ecmdb.ca/proteins/P0AAI9.xml Acyl-CoA thioesterase I P0ADA1 TESA_ECOLI tesA http://ecmdb.ca/proteins/P0ADA1.xml Bifunctional protein aas P31119 AAS_ECOLI aas http://ecmdb.ca/proteins/P31119.xml Long-chain-fatty-acid--CoA ligase P69451 LCFA_ECOLI fadD http://ecmdb.ca/proteins/P69451.xml Acyl carrier protein P0A6A8 ACP_ECOLI acpP http://ecmdb.ca/proteins/P0A6A8.xml a cis-vaccenoyl-[acp] + Water > Hydrogen ion + a holo-[acyl-carrier protein] + Vaccenic acid PW_R002782