1.0 2020-05-05 15:49:37 UTC 2020-05-05 18:39:03 UTC BMDB0109672 LysoPI(20:4(5Z,8Z,11Z,14Z)/0:0) 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phospho-(1'-myo-inositol) 1-Arachidonoylglycerophosphoinositol PI(20:4(5Z,8Z,11Z,14Z)/0:0) 1-Arachidonoyl-gpi 1-Arachidonoyl-glycero-3-phospho-(1'-myo-inositol) 1-Arachidonoyl-glycero-3-phospho-(1’-myo-inositol) 1-Arachidonoyl-lysophosphatidylinositol GPI(20:4(5Z,8Z,11Z,14Z)) GPI(20:4(5Z,8Z,11Z,14Z)/0:0) GPI(20:4) GPI(20:4n6) GPI(20:4n6/0:0) GPI(20:4W6) GPI(20:4W6/0:0) LPI(20:4(5Z,8Z,11Z,14Z)) LPI(20:4(5Z,8Z,11Z,14Z)/0:0) LPI(20:4) LPI(20:4n6) LPI(20:4n6/0:0) LPI(20:4W6) LPI(20:4W6/0:0) LysoPI(20:4(5Z,8Z,11Z,14Z)) LysoPI(20:4) LysoPI(20:4n6) LysoPI(20:4n6/0:0) LysoPI(20:4W6) LysoPI(20:4W6/0:0) Lysophosphatidylinositol(20:4(5Z,8Z,11Z,14Z)) Lysophosphatidylinositol(20:4(5Z,8Z,11Z,14Z)/0:0) Lysophosphatidylinositol(20:4) Lysophosphatidylinositol(20:4n6) Lysophosphatidylinositol(20:4n6/0:0) Lysophosphatidylinositol(20:4W6) Lysophosphatidylinositol(20:4W6/0:0) 1-Arachidonoyl-sn-glycero-3-phospho-D-myo-inositol LysoPI(20:4(5Z,8Z,11Z,14Z)/0:0) C29H49O12P 620.6659 620.296163544 [(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid (2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid 1246430-04-5 CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C29H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(31)39-20-22(30)21-40-42(37,38)41-29-27(35)25(33)24(32)26(34)28(29)36/h6-7,9-10,12-13,15-16,22,24-30,32-36H,2-5,8,11,14,17-21H2,1H3,(H,37,38)/b7-6-,10-9-,13-12-,16-15-/t22-,24-,25-,26+,27-,28-,29-/m1/s1 LXUGKKVCSTYZFK-HYNUQJCBSA-N belongs to the class of organic compounds known as 1-acyl-sn-glycerol-3-phosphoinositols. These are glycerophosphoinositols where the glycerol is acylated only at position O-1 with a fatty acid. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoinositols 1-acyl-sn-glycerol-3-phosphoinositols Carbonyl compounds Carboxylic acid esters Cyclohexanols Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Inositol phosphates Monocarboxylic acids and derivatives Organic oxides Polyols 1-acyl-sn-glycerol-3-phosphoinositol Alcohol Aliphatic homomonocyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Inositol phosphate Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Polyol Secondary alcohol Aliphatic homomonocyclic compounds 1-acyl-sn-glycero-3-phospho-1D-myo-inositol logp 3.41 ALOGPS logs -4.24 ALOGPS logp 2.4 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid ChemAxon average_mass 620.6659 ChemAxon mono_mass 620.296163544 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O ChemAxon formula C29H49O12P ChemAxon inchi InChI=1S/C29H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(31)39-20-22(30)21-40-42(37,38)41-29-27(35)25(33)24(32)26(34)28(29)36/h6-7,9-10,12-13,15-16,22,24-30,32-36H,2-5,8,11,14,17-21H2,1H3,(H,37,38)/b7-6-,10-9-,13-12-,16-15-/t22-,24-,25-,26+,27-,28-,29-/m1/s1 ChemAxon inchikey LXUGKKVCSTYZFK-HYNUQJCBSA-N ChemAxon polar_surface_area 203.44 ChemAxon refractivity 159.85 ChemAxon polarizability 64.86 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 36323 Specdb::CMs 48722 Specdb::CMs 543841 Specdb::CMs 543842 Specdb::CMs 543843 Specdb::CMs 543844 Specdb::CMs 543845 Specdb::CMs 543846 Specdb::CMs 543847 Specdb::CMs 543848 Specdb::CMs 543849 Specdb::CMs 543850 Specdb::CMs 543851 Specdb::CMs 543852 Specdb::CMs 543853 Specdb::CMs 543854 Specdb::CMs 543855 Specdb::CMs 543856 Specdb::CMs 543857 Specdb::CMs 543858 Specdb::CMs 543859 Specdb::CMs 543860 Specdb::CMs 543861 Specdb::CMs 543862 Specdb::CMs 543863 Specdb::MsMs 911869 Specdb::MsMs 911870 Specdb::MsMs 911871 Specdb::MsMs 959278 Specdb::MsMs 959279 Specdb::MsMs 959280 Specdb::MsMs 2458136 Specdb::MsMs 2458137 Specdb::MsMs 2458138 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 83053