2.02012-08-09 09:25:11 -06002015-09-13 12:56:17 -0600ECMDB21506M2MDB001901Margaric acidMargaric acid, also known as heptadecanoic acid, is a saturated fatty acid with a 17-carbon chain. Exogenous propionate can be incorporated by Escherichia coli as a primer to produce lipids with fatty acids of odd chain lengths. 17:0CH31[CH2]151COOHHeptadecanoateHeptadecanoate (ACD/Name 4.0)Heptadecanoic acidHeptadecanoic acid (ACD/Name 4.0)HeptadecoateHeptadecoic acidHeptadecylateHeptadecylic acidMargarateMargaric acidMargarinateMargarinic acidMargarinsaureMargaroateMargaroic acidN-HeptadecanoateN-Heptadecanoic acidN-HeptadecoateN-Heptadecoic acidN-HeptadecylateN-Heptadecylic acidNormal-heptadecanoateNormal-heptadecanoic acidC17H34O2270.4507270.255880332heptadecanoic acidheptadecanoic acid506-12-7CCCCCCCCCCCCCCCCC(O)=OInChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)KEMQGTRYUADPNZ-UHFFFAOYSA-NSolidMembranelogp7.66logs-6.25solubility1.51e-04 g/lmelting_point61.3 oClogp6.7pka_strongest_acidic4.95iupacheptadecanoic acidaverage_mass270.4507mono_mass270.255880332smilesCCCCCCCCCCCCCCCCC(O)=OformulaC17H34O2inchiInChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)inchikeyKEMQGTRYUADPNZ-UHFFFAOYSA-Npolar_surface_area37.3refractivity81.68polarizability36.49rotatable_bond_count15acceptor_count2donor_count1physiological_charge-1formal_charge0Specdb::CMs869Specdb::CMs1825Specdb::CMs3021Specdb::CMs30565Specdb::CMs31405Specdb::CMs31841Specdb::CMs38340Specdb::CMs169994Specdb::EiMs772Specdb::NmrOneD1869Specdb::NmrOneD2413Specdb::NmrOneD3103Specdb::NmrOneD337328Specdb::NmrOneD337329Specdb::NmrOneD337330Specdb::NmrOneD337331Specdb::NmrOneD337332Specdb::NmrOneD337333Specdb::NmrOneD337334Specdb::NmrOneD337335Specdb::NmrOneD337336Specdb::NmrOneD337337Specdb::NmrOneD337338Specdb::NmrOneD337339Specdb::NmrOneD337340Specdb::NmrOneD337341Specdb::NmrOneD337342Specdb::NmrOneD337343Specdb::NmrOneD337344Specdb::NmrOneD337345Specdb::NmrOneD337346Specdb::NmrOneD337347Specdb::MsMs25622Specdb::MsMs25623Specdb::MsMs25624Specdb::MsMs32180Specdb::MsMs32181Specdb::MsMs32182Specdb::MsMs285692Specdb::MsMs285693Specdb::MsMs285694Specdb::MsMs285695Specdb::MsMs285696Specdb::MsMs373935Specdb::MsMs373936Specdb::MsMs373937Specdb::MsMs373938Specdb::MsMs373939Specdb::MsMs438668Specdb::MsMs440429Specdb::MsMs440430Specdb::MsMs440431Specdb::MsMs440432Specdb::MsMs1470866Specdb::MsMs2244397Specdb::MsMs2245696Specdb::MsMs2246560Specdb::NmrTwoD1808HMDB02259104651003332365Margaric_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.ASreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Takala TO, Nuutila P, Pulkki K, Oikonen V, Gronroos T, Savunen T, Vahasilta T, Luotolahti M, Kallajoki M, Bergman J, Forsback S, Knuuti J: 14(R,S)-[18F]Fluoro-6-thia-heptadecanoic acid as a tracer of free fatty acid uptake and oxidation in myocardium and skeletal muscle. Eur J Nucl Med Mol Imaging. 2002 Dec;29(12):1617-22. Epub 2002 Oct 3.12458396Hvid-Jacobsen K, Nielsen SL, Jensen VJ, Thomsen HS: Demonstration of the thoracic duct by 123I heptadecanoic acid. Report of a case. Acta Radiol. 1987 Nov-Dec;28(6):783-4.2962620Steer P, Basu S, Lithell H, Vessby B, Berne C, Lind L: Acute elevations of medium- and long-chain fatty acid have different impacts on endothelium-dependent vasodilation in humans. Lipids. 2003 Jan;38(1):15-9.12669814Van Roosmalen PB, Drummond I: Simultaneous determination by gas chromatography of the major metabolites in urine of toluene, xylenes and styrene. Br J Ind Med. 1978 Feb;35(1):56-60.629890Mertens J, Vanryckeghem W, Bossuyt A: Fast, low-temperature preparation of carrier-free 17-123I-heptadecanoic acid applied for liver and heart scintigraphy. Eur J Nucl Med. 1986;11(9):361-2.3956529Wolk A, Vessby B, Ljung H, Barrefors P: Evaluation of a biological marker of dairy fat intake. Am J Clin Nutr. 1998 Aug;68(2):291-5.9701185http://hmdb.ca/system/metabolites/msds/000/001/842/original/HMDB02259.pdf?13584622843-oxoacyl-[acyl-carrier-protein] synthase 3P0A6R0FABH_ECOLIfabHhttp://ecmdb.ca/proteins/P0A6R0.xml3-oxoacyl-[acyl-carrier-protein] synthase 2P0AAI5FABF_ECOLIfabFhttp://ecmdb.ca/proteins/P0AAI5.xml3-oxoacyl-[acyl-carrier-protein] reductaseP0AEK2FABG_ECOLIfabGhttp://ecmdb.ca/proteins/P0AEK2.xmlAcyl carrier proteinP0A6A8ACP_ECOLIacpPhttp://ecmdb.ca/proteins/P0A6A8.xmlLong-chain fatty acid transport proteinP10384FADL_ECOLIfadLhttp://ecmdb.ca/proteins/P10384.xml