1.0 2016-09-30 22:34:04 UTC 2020-06-04 22:49:43 UTC BMDB0000638 BMDB00638 Dodecanoic acid Dodecanoic acid, also known as dodecanoate or potassium laurate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dodecanoic acid exists in all living species, ranging from bacteria to humans. Dodecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, Dodecanoic acid and coenzyme A can be converted into lauroyl-CoA and L-carnitine; which is catalyzed by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In addition, Dodecanoic acid can be converted into dodecanoic acid; which is catalyzed by the enzyme peroxisomal membrane protein 11C. In cattle, dodecanoic acid is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. Dodecanoic acid is a potentially toxic compound. 1-Undecanecarboxylic acid ABL C12 Fatty acid C12:0 CH3-[CH2]10-COOH Coconut oil fatty acids DAO Dodecoic acid Dodecylcarboxylate Dodecylic acid Duodecyclic acid Duodecylic acid Lauric acid Laurinsaeure Laurostearic acid N-Dodecanoic acid Undecane-1-carboxylic acid Vulvic acid Dodecanoate 1-Undecanecarboxylate Dodecoate Dodecylcarboxylic acid Dodecylate Duodecyclate Duodecylate Laate Laic acid Laurostearate N-Dodecanoate Undecane-1-carboxylate Vulvate Aliphat no. 4 Edenor C 1298-100 Emery 651 Hystrene 9512 Kortacid 1299 Laurate Lunac L 70 Lunac L 98 Neo-fat 12 Neo-fat 12-43 Nissan naa 122 Philacid 1200 Prifac 2920 Univol u 314 1-Dodecanoic acid FA(12:0) Dodecanoic acid C12H24O2 200.3178 200.177630012 dodecanoic acid lauric acid 143-07-7 CCCCCCCCCCCC(O)=O InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) POULHZVOKOAJMA-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Medium-chain fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Aliphatic acyclic compounds Saturated fatty acids Straight chain fatty acids Straight chain fatty acids medium-chain fatty acid straight-chain saturated fatty acid Solid melting_point 44 - 46 °C water_solubility 0.00481 mg/mL logp 4.6 SANGSTER (1993) logp 5.13 ALOGPS logs -4.30 ALOGPS logp 4.48 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac dodecanoic acid ChemAxon average_mass 200.3178 ChemAxon mono_mass 200.177630012 ChemAxon smiles CCCCCCCCCCCC(O)=O ChemAxon formula C12H24O2 ChemAxon inchi InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) ChemAxon inchikey POULHZVOKOAJMA-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 58.68 ChemAxon polarizability 25.85 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Beta Oxidation of Very Long Chain Fatty Acids SMP0087259 Fatty Acid Biosynthesis SMP0087257 Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids SMP0087266 Specdb::CMs 583 Specdb::CMs 1322 Specdb::CMs 3302 Specdb::CMs 29475 Specdb::CMs 29589 Specdb::CMs 29853 Specdb::CMs 29879 Specdb::CMs 30120 Specdb::CMs 30590 Specdb::CMs 31179 Specdb::CMs 32233 Specdb::CMs 37666 Specdb::CMs 146557 Specdb::CMs 1070880 Specdb::EiMs 1020 Specdb::MsIr 697 Specdb::MsIr 698 Specdb::MsIr 699 Specdb::NmrTwoD 1394 Specdb::NmrOneD 1449 Specdb::NmrOneD 2247 Specdb::NmrOneD 2942 Specdb::NmrOneD 4936 Specdb::NmrOneD 4937 Specdb::MsMs 870 Specdb::MsMs 871 Specdb::MsMs 872 Specdb::MsMs 4266 Specdb::MsMs 4267 Specdb::MsMs 4268 Specdb::MsMs 4269 Specdb::MsMs 4270 Specdb::MsMs 4271 Specdb::MsMs 4272 Specdb::MsMs 20732 Specdb::MsMs 20733 Specdb::MsMs 20734 Specdb::MsMs 20819 Specdb::MsMs 20820 Specdb::MsMs 20821 Specdb::MsMs 22283 Specdb::MsMs 22284 Specdb::MsMs 22285 Specdb::MsMs 22370 Specdb::MsMs 22371 Specdb::MsMs 22372 Specdb::MsMs 438031 Specdb::MsMs 438032 Specdb::MsMs 438033 Blood Detected by infra-red spectroscopy and silieic acid columns Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482 doi: 10.3168/jds.S0022-0302(61)89765-8 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 5.8 +/- 0.1 uM Commercial skim milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 9.8 +/- 0.3 uM Commercial 1% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 9.4 +/- 0.3 uM Commercial 2% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 2446.11 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2496.03 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 599.0481 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1297.938 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 599.0481 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 6689.37 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 10.2 +/- 0.2 uM Commercial 3.25% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 6290.01 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 5740.88 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 19.97 +/- 2.03 uM Free fatty acid in raw milk from a Danish Holstein herd by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 21.06 +/- 2.77 uM Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 8.13 +/- 0.19 uM Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 3.33 +/- 0.74 uM Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 17.42 +/- 0.01 uM Free fatty acid in raw milk by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. 1779072 Milk Whole milk Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk 5990.475 +/- 1996.825 uM Raw milk Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. 16899705 Milk 26.0586 +/- 0.42 uM Whole milk Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990 Milk 48.5 +/- 23.4 uM Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate. Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3. 11754544 Milk 19.4 +/- 6.6 uM Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate. Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3. 11754544 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk 6689.364 +/- 2146.587 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk 6190.158 +/- 1847.0632 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk Commercial, conventional whole milk Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X Milk 33946.0597 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 41434.161 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 43430.988 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 53914.33 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Oocyte Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries. McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70. 10793638 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Thyroid Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C02679 3756 DB03017 FDB003010 3893 30805 DODECANOATE C00001221 Lauric_acid 40351 5611 Stepanova, G. A.; Markevich, V. S.; Garanin, V. I.; Stychinskii, G. F. Synthesis of lauric acid. Khimicheskaya Promyshlennost (Moscow, Russian Federation) (1974), (12), 930. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. 16899705 Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. 1779072 Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. 20855010 Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. 5409465 Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. 29570652 van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. 28219465 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00244 Peroxisomal carnitine O-octanoyltransferase O19094 CROT Enzyme BMDBP00246 Carnitine O-palmitoyltransferase 2, mitochondrial Q2KJB7 CPT2 Enzyme BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme BMDBP00509 Acyl-coenzyme A synthetase ACSM1, mitochondrial Q9BEA2 ACSM1 Enzyme BMDBP01876 G-protein coupled receptor 84 Q2KI97 GPR84 Enzyme