InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/b17-15-,23-21-/t42-/m1/s1 |
FORFDCPQKJHEBF-VPUSDGANSA-N |
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC |
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mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via phosphatidylcholine 36:2 )
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View more via ChEBI Ontology
Outgoing
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1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84822)
has functional parent
linoleic acid
(CHEBI:17351)
1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84822)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84822)
has role
mouse metabolite
(CHEBI:75771)
1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84822)
is a
phosphatidylcholine 36:2
(CHEBI:64433)
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(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propyl 2-(trimethylammonio)ethyl phosphate
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(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
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1-18:0-2-18:2-phosphatidylcholine
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MetaCyc
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1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine
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UniProt
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1-stearoyl-2-linoleoyl-GPC
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ChEBI
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1-stearoyl-2-linoleoyl-GPC (18:0/18:2)
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ChEBI
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1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine
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LIPID MAPS
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18:0-18:2-PC
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MetaCyc
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GPC(18:0/18:2)
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ChEBI
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GPCho(18:0/18:2)
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HMDB
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GPCho(18:0/18:2n6)
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HMDB
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GPCho(18:0/18:2w6)
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HMDB
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GPCho(36:2)
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HMDB
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PC(18:0/18:2(9Z,12Z))
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LIPID MAPS
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PC(18:0/18:2)
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HMDB
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PC(18:0/18:2n6)
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HMDB
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PC(18:0/18:2w6)
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HMDB
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PC(36:2)
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HMDB
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phosphatidylcholine (1-18:0-2-18:2)
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MetaCyc
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Phosphatidylcholine(18:0/18:2)
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HMDB
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Phosphatidylcholine(18:0/18:2n6)
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HMDB
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Phosphatidylcholine(36:2)
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HMDB
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27098-24-4
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CAS Registry Number
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ChemIDplus
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6089852
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Reaxys Registry Number
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Reaxys
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Zhou L, Zhao M, Khalil A, Marcic C, Bindler F, Marchioni E (2013) Identification of volatiles from oxidised phosphatidylcholine molecular species using headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS). Analytical and bioanalytical chemistry 405, 9125-9137 [PubMed:24077831] [show Abstract] Headspace solid-phase microextraction (HS-SPME) followed by gas chromatography-mass spectrometry analysis (GC-MS) was used to investigate the volatile compounds from oxidised phosphatidylcholine molecular species. 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine (SOPC) and 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine (SLPC) were chosen as models. The influence of several parameters on the efficiency of volatile oxidised compounds (VOCs) microextraction, such as type of fibre, extraction duration and temperature were studied. The best results were obtained with a polydimethylsiloxane/divinylbenzene (PDMS/DVB) fibre used at 50 °C during 25 min. The effect of oxidation temperature on the yield of VOCs from SOPC and SLPC was investigated. Oxidative kinetics of SOPC and SLPC were investigated by measuring both the production of VOCs and the degradation of starting materials. More than 30 VOCs were detected by means of the reference mass spectra of the National Institute of Standards and Technology mass spectral library, and most of them were further confirmed by comparing their mass spectra and retention time with those obtained from authentic reference compounds under the same analytical conditions. Moreover, the origins of VOCs from oxidised PLs were studied by comparing those obtained from their corresponding triacylglycerides under the same experimental conditions. The main VOCs identified from oxidised SOPC were (E)-2-decenal, nonanal and octanal and from oxidised SLPC were (E)-2-heptenal, (E)-2-octenal and (E, E)-2,4-decadienal. The proposed method was applied to a real food sample, soy lecithin. | Tada K, Goto M, Tamai N, Matsuki H, Kaneshina S (2010) Pressure effect on the bilayer phase transition of asymmetric lipids with an unsaturated acyl chain. Annals of the New York Academy of Sciences 1189, 77-85 [PubMed:20233371] [show Abstract] The bilayer phase transitions of mixed-chain lipids with monounsaturated acyl chain in the sn-2 position, 1-myristoyl-2-oleoyl-sn-glycero-3-phosphocholine (MOPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), and 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine (SOPC), and with a polyunsaturated acyl chain in the sn-2 position, 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine (SLPC), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (SAPC), and 1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine (SDPC), were observed by differential scanning calorimetry (DSC) under ambient pressure and by light-transmittance measurements under high pressure. The DSC thermogram for each lipid bilayer showed only one transition between the lamellar gel and liquid crystalline phases. The introduction of one or two cis double bonds into the sn-2 acyl chain caused the significant depression of the main-transition temperature and an obvious decrease of enthalpy and volume changes associated with the transition. These features are attributable to loose packing of saturated and unsaturated acyl chains in the bilayer gel phase. The existence of four or six double bonds in the sn-2 chain produced no further decrease in the transition temperature, and in fact six double bonds caused a slight increase in the transition temperature. Thermodynamic properties associated with the bilayer phase transition were discussed. | Hanel AM, Gelb MH (1995) Multiple enzymatic activities of the human cytosolic 85-kDa phospholipase A2: hydrolytic reactions and acyl transfer to glycerol. Biochemistry 34, 7807-7818 (Source: SUBMITTER) [PubMed:7794891] [show Abstract] The recombinant human 85-kDa cytosolic phospholipase A2 (cPLA2), when assayed in the presence of glycerol, catalyzes the transfer of acyl chains of radiolabeled phosphatidylcholine and para-substituted phenyl esters of fatty acids to glycerol, in addition to hydrolyzing these substrates. The product of the transacylation reaction is monoacylglycerol (MAG), and the acyl chain is predominantly esterified (> or = 95%) to a primary hydroxyl group of glycerol (sn-1/3); the stereochemistry is not known. Increasing concentrations of glycerol accelerate enzyme turnover both by providing an additional mechanistic pathway for the enzyme-substrate complex to form products and by increasing the intrinsic hydrolytic and transacylation activities of the enzyme. Significant enzymatic hydrolysis of sn-1/3-arachidonylmonoacylglycerol was measured, while sn-1/3-alpha-linolenoyl- and sn-2-arachidonylmonoacylglycerols were not detectably hydrolyzed. 1,3-Propanediol also serves as an acyl acceptor for the enzyme. cPLA2 hydrolyzes analog of lysophosphatidylcholine that lacks the sn-2 hydroxyl group. The enzyme will hydrolyze sn-1-acyl chains of rac-1-(arachidonyl, alpha-linolenoyl, palmitoyl)-2-O-hexadecyl-glycero-3-phosphocholine lipids and transfer the acyl chain to glycerol. Thus, cPLA2 has phospholipase A1 activity but only if an ether linkage rather than an ester linkage is present at the sn-2 position, and it is shown that the sn-1 acyl chains of both enantiomers of phosphatidylcholine are hydrolyzed. Phenyl [14C]-alpha-linolenate and five para-substituted phenyl esters of [3H]-alpha-linolenic acid with pKa values ranging from 7.2 to 10.2 for the phenol leaving groups were incorporated into 1,2-ditetradecyl-sn-glycero-3-phosphomethanol/Triton X-100 mixed micelles as substrates for the transacylation/hydrolysis reactions of the enzyme. Average product ratios, which are defined as the amount of monoacylglycerol formed to phenyl ester hydrolyzed, were 2.1 +/- 0.1 (n = 5) for the para-substituted phenyl esters and 2.0 +/- 0.3 (n = 7) for phenyl alpha-linolenate. The similarity of the ratios, despite the range of pKa values for the leaving groups, is consistent with the formation of a common enzyme intermediate that partitions to give either fatty acid or MAG. That intermediate may be a covalent acyl enzyme. Finally, the acyl chain specificity of cPLA2 was investigated to better understand the preference of the enzyme for phospholipids with sn-2-arachidonyl chains. | Keough KM, Parsons CS (1990) Differential scanning calorimetry of dispersions of products of oxidation of 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine. Biochemistry and cell biology = Biochimie et biologie cellulaire 68, 300-307 [PubMed:2350495] [show Abstract] Ultraviolet light was used to promote the autoxidation of 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine (SLPC). The extent of oxidation was monitored by ultraviolet spectroscopy, reaction with thiobarbituric acid, fatty acid analysis, and thin-layer chromatography. Fatty acid analysis and thin-layer chromatography appeared to provide the most consistent estimates of oxidation, especially when extensive oxidation had taken place. The oxidized samples were separated by flash chromatography into fractions enriched in different oxidation products. Differential scanning calorimetry of aqueous dispersions of these fractions indicated that oxidation products had higher transition temperatures than the original SLPC. |
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