2.0 2012-08-09 09:16:12 -0600 2015-09-13 12:56:16 -0600 ECMDB21428 M2MDB001823 Stearic acid Stearic acid, also called octadecanoic acid, is one of the useful types of saturated fatty acids. It is a waxy solid, and its chemical formula is CH3(CH2)16COOH. Its name comes from the Greek word stear, which means tallow. (Wikipedia) 1-Heptadecanecarboxylate 1-Heptadecanecarboxylic acid N-Octadecanoate N-Octadecanoic acid Octadecanoate Octadecanoic acid Stearate Stearate cherry Stearex Beads Stearic acid Cherry Stearophanate Stearophanic acid C18H36O2 284.4772 284.271530396 octadecanoic acid stearic acid 57-11-4 CCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) QIQXTHQIDYTFRH-UHFFFAOYSA-N Solid Membrane logp 8.02 ALOGPS logs -6.63 ALOGPS solubility 6.61e-05 g/l ALOGPS melting_point 68.8 oC logp 7.15 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac octadecanoic acid ChemAxon average_mass 284.4772 ChemAxon mono_mass 284.271530396 ChemAxon smiles CCCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C18H36O2 ChemAxon inchi InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) ChemAxon inchikey QIQXTHQIDYTFRH-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 86.29 ChemAxon polarizability 38.64 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon fatty acid oxidation (steareate) 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 thiolase PW001024 Metabolic Specdb::CMs 653 Specdb::CMs 654 Specdb::CMs 655 Specdb::CMs 1893 Specdb::CMs 3276 Specdb::CMs 29808 Specdb::CMs 29854 Specdb::CMs 30406 Specdb::CMs 30655 Specdb::CMs 30934 Specdb::CMs 31238 Specdb::CMs 31893 Specdb::CMs 37789 Specdb::CMs 132451 Specdb::CMs 140185 Specdb::CMs 1077679 Specdb::EiMs 171 Specdb::NmrOneD 1558 Specdb::NmrOneD 2484 Specdb::NmrOneD 3180 Specdb::NmrOneD 4942 Specdb::NmrOneD 4943 Specdb::NmrOneD 166540 Specdb::NmrOneD 340728 Specdb::NmrOneD 340729 Specdb::NmrOneD 340730 Specdb::NmrOneD 340731 Specdb::NmrOneD 340732 Specdb::NmrOneD 340733 Specdb::NmrOneD 340734 Specdb::NmrOneD 340735 Specdb::NmrOneD 340736 Specdb::NmrOneD 340737 Specdb::NmrOneD 340738 Specdb::NmrOneD 340739 Specdb::NmrOneD 340740 Specdb::NmrOneD 340741 Specdb::NmrOneD 340742 Specdb::NmrOneD 340743 Specdb::NmrOneD 340744 Specdb::NmrOneD 340745 Specdb::NmrOneD 340746 Specdb::MsMs 1176 Specdb::MsMs 1177 Specdb::MsMs 20834 Specdb::MsMs 20835 Specdb::MsMs 20836 Specdb::MsMs 20894 Specdb::MsMs 20895 Specdb::MsMs 20896 Specdb::MsMs 22385 Specdb::MsMs 22386 Specdb::MsMs 22387 Specdb::MsMs 22445 Specdb::MsMs 22446 Specdb::MsMs 22447 Specdb::MsMs 285542 Specdb::MsMs 285543 Specdb::MsMs 285544 Specdb::MsMs 285545 Specdb::MsMs 373949 Specdb::MsMs 373950 Specdb::MsMs 373951 Specdb::MsMs 373952 Specdb::MsMs 438640 Specdb::MsMs 440440 Specdb::MsMs 440441 Specdb::NmrTwoD 1500 HMDB00827 5281 5091 C01530 28842 STE Stearic 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 Hoffmann 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. 8412012 Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. 15854043 Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. 10391868 Sanjurjo P, Rodriguez-Alarcon J, Rodriguez-Soriano J: Plasma fatty acid composition during the first week of life following feeding with human milk or formula. Acta Paediatr Scand. 1988 Mar;77(2):202-6. 3354331 Neoptolemos JP, Thomas BS: Erythrocyte membrane stearic acid: oleic acid ratios in colorectal cancer using tube capillary column gas liquid chromatography. Ann Clin Biochem. 1990 Jan;27 ( Pt 1):38-43. 2310156 Turpeinen AM, Wubert J, Aro A, Lorenz R, Mutanen M: Similar effects of diets rich in stearic acid or trans-fatty acids on platelet function and endothelial prostacyclin production in humans. Arterioscler Thromb Vasc Biol. 1998 Feb;18(2):316-22. 9484999 Daubresse JC: [Atherosclerosis and nutrition] Rev Med Brux. 2000 Sep;21(4):A359-62. 11068494 Hoppu U, Rinne M, Lampi AM, Isolauri E: Breast milk fatty acid composition is associated with development of atopic dermatitis in the infant. J Pediatr Gastroenterol Nutr. 2005 Sep;41(3):335-8. 16131990 Musial W, Kubis A: Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum. Eur J Pharm Biopharm. 2003 Mar;55(2):237-40. 12637103 Doran TA, Ford JA, Allen LC, Wong PY, Benzie RJ: Amniotic fluid lecithin/sphingomyelin ratio, palmitic acid, palmitic acid/stearic acid ratio, total cortisol, creatinine, and percentage of lipid-positive cells in assessment of fetal maturity and fetal pulmonary maturity: a comparison. Am J Obstet Gynecol. 1979 Feb 1;133(3):302-7. 433991 Kazmierczak SC, Gurachevsky A, Matthes G, Muravsky V: Electron spin resonance spectroscopy of serum albumin: a novel new test for cancer diagnosis and monitoring. Clin Chem. 2006 Nov;52(11):2129-34. Epub 2006 Sep 21. 16990414 Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D: A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr. 2001 Feb;55(2):88-96. 11305631 Diani F, Cacco M, Molinaroli A, Cerruti G, Meloncelli C, Turinetto A: [Fatty acid composition of the cervical mucus obtained during ovulation and at the term of pregnancy] Minerva Ginecol. 1998 Oct;50(10):405-10. 9866950 http://hmdb.ca/system/metabolites/msds/000/000/745/original/HMDB00827.pdf?1358895881 Malonyl CoA-acyl carrier protein transacylase P0AAI9 FABD_ECOLI fabD http://ecmdb.ca/proteins/P0AAI9.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 Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Acyl carrier protein P0A6A8 ACP_ECOLI acpP http://ecmdb.ca/proteins/P0A6A8.xml Stearic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Stearoyl-CoA + Stearoyl-CoA PW_R003765