2.02012-08-09 09:16:12 -06002015-09-13 15:15:33 -0600ECMDB21427M2MDB001822Myristic acidMyristic acid ia a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. 1-Tridecanecarboxylate1-Tridecanecarboxylic acidCrodacidMyristateMyristate pureMyristic acid pureMyristoateMyristoic acidN-Tetradecan-1-oateN-Tetradecan-1-oic acidN-TetradecanoateN-Tetradecanoic acidTetradecanoateTetradecanoic (Myristic) acidTetradecanoic acidC14H28O2228.3709228.20893014tetradecanoic acidmyristic acid544-63-8CCCCCCCCCCCCCC(O)=OInChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)TUNFSRHWOTWDNC-UHFFFAOYSA-NSolidMembranelogp6.10logs-5.12solubility1.72e-03 g/lmelting_point53.9 oClogp5.37pka_strongest_acidic4.95iupactetradecanoic acidaverage_mass228.3709mono_mass228.20893014smilesCCCCCCCCCCCCCC(O)=OformulaC14H28O2inchiInChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)inchikeyTUNFSRHWOTWDNC-UHFFFAOYSA-Npolar_surface_area37.3refractivity67.88polarizability30.1rotatable_bond_count12acceptor_count2donor_count1physiological_charge-1formal_charge0fatty acid oxidation (myristate)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 thiolasePW001021MetabolicSpecdb::CMs1532Specdb::CMs3066Specdb::CMs31233Specdb::CMs32057Specdb::CMs37776Specdb::CMs149963Specdb::CMs1077403Specdb::EiMs1256Specdb::NmrOneD1549Specdb::NmrOneD3140Specdb::NmrOneD4938Specdb::NmrOneD4939Specdb::MsMs1150Specdb::MsMs1151Specdb::MsMs4682Specdb::MsMs4683Specdb::MsMs4684Specdb::MsMs4685Specdb::MsMs4686Specdb::MsMs20609Specdb::MsMs20610Specdb::MsMs20611Specdb::MsMs21182Specdb::MsMs21183Specdb::MsMs21184Specdb::MsMs22160Specdb::MsMs22161Specdb::MsMs22162Specdb::MsMs22733Specdb::MsMs22734Specdb::MsMs22735Specdb::MsMs285538Specdb::MsMs285539Specdb::MsMs285540Specdb::MsMs285541Specdb::MsMs373909Specdb::MsMs373910Specdb::NmrTwoD1493HMDB008061100510539C0642428875MYRMyristic 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):910-4.19212411Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.12829005Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.8412012Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4.11124748Dabadie H, Peuchant E, Bernard M, LeRuyet P, Mendy F: Moderate intake of myristic acid in sn-2 position has beneficial lipidic effects and enhances DHA of cholesteryl esters in an interventional study. J Nutr Biochem. 2005 Jun;16(6):375-82.15936650Majeti BK, Karmali PP, Madhavendra SS, Chaudhuri A: Example of fatty acid-loaded lipoplex in enhancing in vitro gene transfer efficacies of cationic amphiphile. Bioconjug Chem. 2005 May-Jun;16(3):676-84.15898737Schewe T, Hiebsch C: [Action of respiratory inhibitors on the electron transport system of Escherichia coli] Acta Biol Med Ger. 1977;36(7-8):961-6.347849Curry S, Brick P, Franks NP: Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta. 1999 Nov 23;1441(2-3):131-40.10570241Kageura M, Hara K, Hieda Y, Takamoto M, Fujiwara Y, Fukuma Y, Kashimura S: [Screening of drugs and chemicals by wide-bore capillary gas chromatography with flame ionization and nitrogen phosphorus detectors] Nihon Hoigaku Zasshi. 1989 Apr;43(2):161-5.2810891Zhu W, Smart EJ: Myristic acid stimulates endothelial nitric-oxide synthase in a CD36- and an AMP kinase-dependent manner. J Biol Chem. 2005 Aug 19;280(33):29543-50. Epub 2005 Jun 21.15970594Bhattacharya A, Ghosal SK: Permeation kinetics of ketotifen fumarate alone and in combination with hydrophobic permeation enhancers through human cadaver epidermis. Boll Chim Farm. 2000 Jul-Aug;139(4):177-81.11059101Matsubara M: [Structures and molecular recognition of MARCKS family proteins] Seikagaku. 2005 Jan;77(1):50-5.15770953Kaminskas A, Zieden B, Elving B, Kristenson M, Abaravicius A, Bergdahl B, Olsson AG, Kucinskiene Z: Adipose tissue fatty acids in men from two populations with different cardiovascular risk: the LiVicordia study. Scand J Clin Lab Invest. 1999 May;59(3):227-32.10400167Brod SA, Malone M, Darcan S, Papolla M, Nelson L: Ingested interferon alpha suppresses type I diabetes in non-obese diabetic mice. Diabetologia. 1998 Oct;41(10):1227-32.9794112Pieterse Z, Jerling JC, Oosthuizen W, Kruger HS, Hanekom SM, Smuts CM, Schutte AE: Substitution of high monounsaturated fatty acid avocado for mixed dietary fats during an energy-restricted diet: effects on weight loss, serum lipids, fibrinogen, and vascular function. Nutrition. 2005 Jan;21(1):67-75.15661480Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30.http://hmdb.ca/system/metabolites/msds/000/000/724/original/HMDB00806.pdf?1358894981Malonyl CoA-acyl carrier protein transacylaseP0AAI9FABD_ECOLIfabDhttp://ecmdb.ca/proteins/P0AAI9.xmlBifunctional protein aasP31119AAS_ECOLIaashttp://ecmdb.ca/proteins/P31119.xmlLong-chain-fatty-acid--CoA ligaseP69451LCFA_ECOLIfadDhttp://ecmdb.ca/proteins/P69451.xmlShort-chain-fatty-acid--CoA ligaseP38135FADK_ECOLIfadKhttp://ecmdb.ca/proteins/P38135.xmlAcyl carrier proteinP0A6A8ACP_ECOLIacpPhttp://ecmdb.ca/proteins/P0A6A8.xmlMyristic acid + Coenzyme A + Adenosine triphosphate > Adenosine monophosphate + Tetradecanoyl-CoAPW_R003762