1.0 2011-09-21 01:32:03 UTC 2015-07-21 06:59:16 UTC FDB027923 PC(18:1(9Z)e/2:0) 2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine is an intermediate in ether lipid metabolism. 2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine is converted from 2-acetyl-1-octadecyl-sn-glycerol via diacylglycerol cholinephosphotransferase (EC: 2.7.8.2). This is an ether lipid with platelet-activating factor functions which has an acetyl group instead of an acyl chain at the second position (SN-2). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. [HMDB] (2-Acetyloxy-3-octadec-9-enoxypropyl) 2-trimethylazaniumylethyl ate (2-acetyloxy-3-octadec-9-enoxypropyl) 2-trimethylazaniumylethyl phosphate 2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-ocholine 2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine PC(o-18:1(9Z)/2:0) C28H56NO7P 549.7205 549.379439663 (2-{[(2R)-2-(acetyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2R)-2-(acetyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium [H][C@@](COCCCCCCCCC=CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O InChI=1S/C28H56NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h13-14,28H,6-12,15-26H2,1-5H3/t28-/m1/s1 ZBOQHUSCQCEBGK-MUUNZHRXSA-N belongs to the class of organic compounds known as 1-alkyl,2-acetylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acetyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. 1-alkyl,2-acetylglycero-3-phosphocholines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Aliphatic acyclic compounds Amines Carbonyl compounds Carboxylic acid esters Dialkyl ethers Dialkyl phosphates Glycerol ethers Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Tetraalkylammonium salts 1-alkyl,2-acetylglycero-3-phosphocholine Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Dialkyl phosphate Ether Glycerol ether 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 Tetraalkylammonium salt Solid logp 3.14 ALOGPS logs -6.60 ALOGPS solubility 1.50e-04 g/l ALOGPS logp 2.54 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2-{[(2R)-2-(acetyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 549.7205 ChemAxon mono_mass 549.379439663 ChemAxon smiles [H][C@@](COCCCCCCCCC=CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O ChemAxon formula C28H56NO7P ChemAxon inchi InChI=1S/C28H56NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h13-14,28H,6-12,15-26H2,1-5H3/t28-/m1/s1 ChemAxon inchikey ZBOQHUSCQCEBGK-MUUNZHRXSA-N ChemAxon polar_surface_area 94.12 ChemAxon refractivity 161.99 ChemAxon polarizability 66.06 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB11148 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 Choline kinase alpha P35790 CHKA Choline-phosphate cytidylyltransferase A P49585 PCYT1A Choline-phosphate cytidylyltransferase B Q9Y5K3 PCYT1B Lecithin retinol acyltransferase O95237 LRAT Lysophosphatidylcholine acyltransferase 2 Q7L5N7 LPCAT2 Lysophospholipid acyltransferase 5 Q6P1A2 LPCAT3 Neuropathy target esterase Q8IY17 PNPLA6 Phosphatidylcholine-sterol acyltransferase P04180 LCAT Phosphatidylcholine:ceramide cholinephosphotransferase 1 Q86VZ5 SGMS1 Phosphatidylcholine:ceramide cholinephosphotransferase 2 Q8NHU3 SGMS2 Phosphatidylethanolamine-binding protein 1 P30086 PEBP1 Phosphatidylethanolamine-binding protein 4 Q96S96 PEBP4 Phosphatidylserine synthase 1 P48651 PTDSS1 Phospholipase D2 O14939 PLD2 Phospholipase D3 Q8IV08 PLD3 Phospholipase D4 Q96BZ4 PLD4 Phospholipase D6 Q8N2A8 PLD6 Platelet-activating factor acetylhydrolase 2, cytoplasmic Q99487 PAFAH2 Platelet-activating factor acetylhydrolase IB subunit beta P68402 PAFAH1B2 Platelet-activating factor acetylhydrolase IB subunit gamma Q15102 PAFAH1B3