2.0 2012-08-09 09:25:11 -0600 2015-09-13 12:56:17 -0600 ECMDB21506 M2MDB001901 Margaric acid Margaric 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. 17:0 CH31[CH2]151COOH Heptadecanoate Heptadecanoate (ACD/Name 4.0) Heptadecanoic acid Heptadecanoic acid (ACD/Name 4.0) Heptadecoate Heptadecoic acid Heptadecylate Heptadecylic acid Margarate Margaric acid Margarinate Margarinic acid Margarinsaure Margaroate Margaroic acid N-Heptadecanoate N-Heptadecanoic acid N-Heptadecoate N-Heptadecoic acid N-Heptadecylate N-Heptadecylic acid Normal-heptadecanoate Normal-heptadecanoic acid C17H34O2 270.4507 270.255880332 heptadecanoic acid heptadecanoic acid 506-12-7 CCCCCCCCCCCCCCCCC(O)=O InChI=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-N Solid Membrane logp 7.66 ALOGPS logs -6.25 ALOGPS solubility 1.51e-04 g/l ALOGPS melting_point 61.3 oC logp 6.7 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac heptadecanoic acid ChemAxon average_mass 270.4507 ChemAxon mono_mass 270.255880332 ChemAxon smiles CCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C17H34O2 ChemAxon inchi InChI=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) ChemAxon inchikey KEMQGTRYUADPNZ-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 81.68 ChemAxon polarizability 36.49 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 869 Specdb::CMs 1825 Specdb::CMs 3021 Specdb::CMs 30565 Specdb::CMs 31405 Specdb::CMs 31841 Specdb::CMs 38340 Specdb::CMs 169994 Specdb::EiMs 772 Specdb::NmrOneD 1869 Specdb::NmrOneD 2413 Specdb::NmrOneD 3103 Specdb::NmrOneD 337328 Specdb::NmrOneD 337329 Specdb::NmrOneD 337330 Specdb::NmrOneD 337331 Specdb::NmrOneD 337332 Specdb::NmrOneD 337333 Specdb::NmrOneD 337334 Specdb::NmrOneD 337335 Specdb::NmrOneD 337336 Specdb::NmrOneD 337337 Specdb::NmrOneD 337338 Specdb::NmrOneD 337339 Specdb::NmrOneD 337340 Specdb::NmrOneD 337341 Specdb::NmrOneD 337342 Specdb::NmrOneD 337343 Specdb::NmrOneD 337344 Specdb::NmrOneD 337345 Specdb::NmrOneD 337346 Specdb::NmrOneD 337347 Specdb::MsMs 25622 Specdb::MsMs 25623 Specdb::MsMs 25624 Specdb::MsMs 32180 Specdb::MsMs 32181 Specdb::MsMs 32182 Specdb::MsMs 285692 Specdb::MsMs 285693 Specdb::MsMs 285694 Specdb::MsMs 285695 Specdb::MsMs 285696 Specdb::MsMs 373935 Specdb::MsMs 373936 Specdb::MsMs 373937 Specdb::MsMs 373938 Specdb::MsMs 373939 Specdb::MsMs 438668 Specdb::MsMs 440429 Specdb::MsMs 440430 Specdb::MsMs 440431 Specdb::MsMs 440432 Specdb::MsMs 1470866 Specdb::MsMs 2244397 Specdb::MsMs 2245696 Specdb::MsMs 2246560 Specdb::NmrTwoD 1808 HMDB02259 10465 10033 32365 Margaric_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 Sreekumar 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. 19212411 Takala 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. 12458396 Hvid-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. 2962620 Steer 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. 12669814 Van 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. 629890 Mertens 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. 3956529 Wolk 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. 9701185 http://hmdb.ca/system/metabolites/msds/000/001/842/original/HMDB02259.pdf?1358462284 3-oxoacyl-[acyl-carrier-protein] synthase 3 P0A6R0 FABH_ECOLI fabH http://ecmdb.ca/proteins/P0A6R0.xml 3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI fabF http://ecmdb.ca/proteins/P0AAI5.xml 3-oxoacyl-[acyl-carrier-protein] reductase P0AEK2 FABG_ECOLI fabG http://ecmdb.ca/proteins/P0AEK2.xml Acyl carrier protein P0A6A8 ACP_ECOLI acpP http://ecmdb.ca/proteins/P0A6A8.xml Long-chain fatty acid transport protein P10384 FADL_ECOLI fadL http://ecmdb.ca/proteins/P10384.xml