1.0 2016-10-03 18:05:34 UTC 2020-06-04 20:10:48 UTC BMDB0010386 BMDB0062752 BMDB10386 BMDB62752 LysoPC(18:2(9Z,12Z)/0:0) Lysopc(18:2(9Z,12Z)), also known as LPC 18:2(9Z,12Z)/0:0 or LPC(18:2n6/0:0), belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Thus, lysopc(18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. Lysopc(18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lysopc(18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. 1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholine 1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholine 1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholine 1-18:2-LysoPC 1-Linoleoyl-glycero-3-phosphocholine 1-Linoleoyl-GPC 1-Linoleoyl-GPC (18:2) 1-Linoleoylglycerophosphocholine GPC(18:2) GPC(18:2/0:0) LPC 18:2(9Z,12Z)/0:0 LPC(18:2) LPC(18:2/0:0) LPC(18:2n6/0:0) LPC(18:2Omega6/0:0) LyPC(18:2) LyPC(18:2n6/0:0) LyPC(18:2omega6/0:0) LysoPC 18:2(9Z,12Z)/0:0 LysoPC(18:2) LysoPC(18:2/0:0) LysoPC(18:2n6/0:0) LysoPC(18:2omega6/0:0) Lysophosphatidylcholine(18:2(9Z,12Z)/0:0) Lysophosphatidylcholine(18:2) Lysophosphatidylcholine(18:2/0:0) Lysophosphatidylcholine(18:2n6/0:0) Lysophosphatidylcholine(18:2omega6/0:0) PC 18:2(9Z,12Z)/0:0 PC(18:2(9Z,12Z)/0:0) LyPC(18:2/0:0) LysoPC(18:2(9Z,12Z)) 1-Linoleoyl lysolecithin 1-Linoleoyl-sn-glycero-3-phosphorylcholine 1-Linoleoylglycerol-3-phosphorylcholine 1-Linoleoylphosphatidylcholine Linoleoyllysolecithin Linoleyl lysophosphatidylcholine Lysophosphatidylcholine 18:2 1-Linoleoyl-lysophosphatidylcholine 1-Linoleoyl-sn-glycero-3-phosphocholine GPC(18:2(9Z,12Z)) GPC(18:2(9Z,12Z)/0:0) GPC(18:2n6) GPC(18:2n6/0:0) GPC(18:2W6) GPC(18:2W6/0:0) LPC(18:2(9Z,12Z)) LPC(18:2(9Z,12Z)/0:0) LPC(18:2n6) LPC(18:2W6) LPC(18:2W6/0:0) LysoPC(18:2n6) LysoPC(18:2W6) LysoPC(18:2W6/0:0) Lysophosphatidylcholine(18:2(9Z,12Z)) Lysophosphatidylcholine(18:2n6) Lysophosphatidylcholine(18:2W6) Lysophosphatidylcholine(18:2W6/0:0) LysoPC(18:2(9Z,12Z)/0:0) C26H50NO7P 519.6515 519.332489471 (2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium 22252-07-9 [H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1 SPJFYYJXNPEZDW-FTJOPAKQSA-N belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines 1-acyl-sn-glycero-3-phosphocholines Amines Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Secondary alcohols Tetraalkylammonium salts 1-acyl-sn-glycero-3-phosphocholine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoric acid ester Quaternary ammonium salt Secondary alcohol Tetraalkylammonium salt Aliphatic acyclic compounds 1-O-acyl-sn-glycero-3-phosphocholine Monoacylglycerophosphocholines lysophosphatidylcholine 18:2 Solid logp 2.22 ALOGPS logs -6.34 ALOGPS logp 1.36 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 519.6515 ChemAxon mono_mass 519.332489471 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C26H50NO7P ChemAxon inchi InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1 ChemAxon inchikey SPJFYYJXNPEZDW-FTJOPAKQSA-N ChemAxon polar_surface_area 105.12 ChemAxon refractivity 153.71 ChemAxon polarizability 58.75 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 39495 Specdb::MsMs 2441548 Specdb::MsMs 2441549 Specdb::MsMs 2441550 Specdb::MsMs 2458837 Specdb::MsMs 2458838 Specdb::MsMs 2458839 Specdb::MsMs 2476814 Specdb::MsMs 2476815 Specdb::MsMs 2476816 Specdb::MsMs 2862700 Specdb::MsMs 2862701 Specdb::MsMs 2862702 Specdb::MsMs 2910983 Specdb::MsMs 2910984 Specdb::MsMs 2910985 Specdb::NmrOneD 336078 Specdb::NmrOneD 336079 Specdb::NmrOneD 336080 Specdb::NmrOneD 336081 Specdb::NmrOneD 336082 Specdb::NmrOneD 336083 Specdb::NmrOneD 336084 Specdb::NmrOneD 336085 Specdb::NmrOneD 336086 Specdb::NmrOneD 336087 Specdb::NmrOneD 336088 Specdb::NmrOneD 336089 Specdb::NmrOneD 336090 Specdb::NmrOneD 336091 Specdb::NmrOneD 336092 Specdb::NmrOneD 336093 Specdb::NmrOneD 336094 Specdb::NmrOneD 336095 Specdb::NmrOneD 336096 Specdb::NmrOneD 336097 All Tissues 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 Blood Detected by DFI-MS/MS (P180) in periparturient Holstein cows. Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13. 24630653 Blood 15 +/- 3 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Blood 30-186 uM By LC-MS/MS Artegoitia VM, Middleton JL, Harte FM, Campagna SR, de Veth MJ: Choline and choline metabolite patterns and associations in blood and milk during lactation in dairy cows. PLoS One. 2014 Aug 26;9(8):e103412. doi: 10.1371/journal.pone.0103412. eCollection 2014. 25157578 Blood 4.31 +/- 2.3 uM Detected by DFI-MS/MS (P180) 4 week before parturition Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13. 24630653 Blood Detected by electrospray ionization tandem mass spectrometry with the Biocrates AbsoluteIDQ in male Charolais and Holstein cows. Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20. 20647382 Liver 1.1 +/- 0.3 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 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 Longissimus Thoracis Muscle 0.3 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Milk 0.181 +/- 0.002 uM Commercial skim milk by LC-HRMS 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 0.164 +/- 0.004 uM Commercial 1% milk by LC-HRMS 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 0.19 +/- 0.01 uM Commercial 2% milk by LC-HRMS 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 0.185 +/- 0.004 uM Commercial 3.25% milk by LC-HRMS 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 Placenta 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 Ruminal Fluid 0.2 +/- 0.1 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Ruminal Fluid 0.16 +/- 0.04 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.09 +/- 0.04 uM Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Semimembranosus Muscle 0.4 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 0.41 +/- 0.13 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 9181014 11005824 FDB030316 28733 CPD-8347 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)