{"ymdb_id":"YMDB01163","created_at":"2011-07-24T19:08:34.000Z","updated_at":"2016-10-18T17:11:49.000Z","name":"PA(16:0/18:1(9Z))","cas":null,"state":"Solid","melting_point":null,"description":"PA(16:0/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain  to the C-1 atom, and  one 9Z-octadecenoyl  to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":null,"synthesis_reference":null,"chebi_id":"16337","hmdb_id":"HMDB07859","kegg_id":"C00416","pubchem_id":"128989","cs_id":"4446637","foodb_id":null,"wikipedia_link":"Lecithin","biocyc_id":"L-PHOSPHATIDATE","iupac":"[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid","traditional_iupac":"(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid","logp":"12.406743423999998","pka":"6.343234649149876","alogps_solubility":"7.74e-05 g/l","alogps_logp":"8.91","alogps_logs":"-6.94","acceptor_count":"5","donor_count":"2","rotatable_bond_count":"37","polar_surface_area":"119.36000000000001","refractivity":"188.8904","polarizability":"82.82632040752232","formal_charge":"0","physiological_charge":"-2","pka_strongest_basic":"-6.744159310865181","pka_strongest_acidic":"1.3174060830586427","bioavailability":"0","number_of_rings":"0","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidic acid","1-palmitoyl-2-oleoyl-sn-glycero-3-phosphate","1,2-Diacyl-sn-glycerol 3-phosphate","3-sn-Phosphatidate","PA(16:0/18:1)","PA(16:0/18:1n9)","PA(16:0/18:1w9)","PA(34:1)","Phosphatidate","Phosphatidic acid","Phosphatidic acid(16:0/18:1)","Phosphatidic acid(16:0/18:1n9)","Phosphatidic acid(16:0/18:1w9)","Phosphatidic acid(34:1)","phosphatidic acids"],"pathways":[{"name":"Glycerolipid metabolism","kegg_map_id":"00561"},{"name":"Glycerophospholipid metabolism","kegg_map_id":"00564"},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(11Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:0)","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:1(11Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:1(13Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:0)","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:1(11Z))","kegg_map_id":null},{"name":"Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:1(13Z))","kegg_map_id":null}],"growth_conditions":[{"growth_media":"SD media with 2% raffinose","concentration":"491500.0","concentration_units":"umol/L","error":"48650.0"},{"growth_media":"SD media with 2% raffinose","concentration":"714750.0","concentration_units":"umol/L","error":"53850.0"}],"references":[{"pubmed_id":19174513,"citation":"Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). \"Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry.\" Proc Natl Acad Sci U S A 106:2136-2141."},{"pubmed_id":9401016,"citation":"Athenstaedt, K., Daum, G. (1997). \"Biosynthesis of phosphatidic acid in lipid particles and endoplasmic reticulum of Saccharomyces cerevisiae.\" J Bacteriol 179:7611-7616."},{"pubmed_id":8618862,"citation":"Rose, K., Rudge, S. A., Frohman, M. A., Morris, A. J., Engebrecht, J. (1995). \"Phospholipase D signaling is essential for meiosis.\" Proc Natl Acad Sci U S A 92:12151-12155."},{"pubmed_id":8557688,"citation":"Shen, H., Heacock, P. N., Clancey, C. J., Dowhan, W. (1996). \"The CDS1 gene encoding CDP-diacylglycerol synthase in Saccharomyces cerevisiae is essential for cell growth.\" J Biol Chem 271:789-795."},{"pubmed_id":10685032,"citation":"Furneisen, J. M., Carman, G. M. (2000). \"Enzymological properties of the LPP1-encoded lipid phosphatase from Saccharomyces cerevisiae.\" Biochim Biophys Acta 1484:71-82."},{"pubmed_id":9452443,"citation":"Toke, D. A., Bennett, W. L., Dillon, D. A., Wu, W. I., Chen, X., Ostrander, D. B., Oshiro, J., Cremesti, A., Voelker, D. R., Fischl, A. S., Carman, G. M. (1998). \"Isolation and characterization of the Saccharomyces cerevisiae DPP1 gene encoding diacylglycerol pyrophosphate phosphatase.\" J Biol Chem 273:3278-3284."}],"proteins":[]}