Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 02:54:25 UTC |
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Update Date | 2022-11-30 19:25:56 UTC |
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HMDB ID | HMDB0114857 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(16:1(9Z)/18:3(6Z,9Z,12Z)) |
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Description | PA(16:1(9Z)/18:3(6Z,9Z,12Z)) 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(16:1(9Z)/18:3(6Z,9Z,12Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of gamma-linolenic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
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Structure | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C37H65O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,22,24,35H,3-10,12,15,19-21,23,25-34H2,1-2H3,(H2,40,41,42)/b13-11-,16-14-,18-17-,24-22-/t35-/m1/s1 |
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Synonyms | Value | Source |
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1-palmitoleoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-palmitoleoyl-2-gamma-linolenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(16:1/18:3) | SMPDB, HMDB | PA(16:1n7/18:3n6) | SMPDB, HMDB | PA(16:1w7/18:3w6) | SMPDB, HMDB | PA(34:4) | SMPDB, HMDB | Phosphatidic acid(16:1(9Z)/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidic acid(16:1/18:3) | SMPDB, HMDB | Phosphatidic acid(16:1n7/18:3n6) | SMPDB, HMDB | Phosphatidic acid(16:1w7/18:3w6) | SMPDB, HMDB | Phosphatidic acid(34:4) | SMPDB, HMDB | Phosphatidate(16:1(9Z)/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidate(16:1/18:3) | SMPDB, HMDB | Phosphatidate(16:1n7/18:3n6) | SMPDB, HMDB | Phosphatidate(16:1w7/18:3w6) | SMPDB, HMDB | Phosphatidate(34:4) | SMPDB, HMDB | PA(16:1(9Z)/18:3(6Z,9Z,12Z)) | SMPDB |
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Chemical Formula | C37H65O8P |
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Average Molecular Weight | 668.893 |
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Monoisotopic Molecular Weight | 668.441706051 |
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IUPAC Name | [(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C37H65O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,22,24,35H,3-10,12,15,19-21,23,25-34H2,1-2H3,(H2,40,41,42)/b13-11-,16-14-,18-17-,24-22-/t35-/m1/s1 |
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InChI Key | JYOCUILAZUIHCV-ZKAVACCVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphates |
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Direct Parent | 1,2-diacylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/16:1(9Z)) (PathBank: SMP0021457)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0021458)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0021459)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0021460)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0021461)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0021462)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z)) (PathBank: SMP0021463)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0021464)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0021465)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0021466)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0021467)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0021468)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0021469)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0021470)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0021471)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0021472)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0021473)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021474)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021475)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (PathBank: SMP0032855)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0032856)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0065590)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0065598)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:0) (PathBank: SMP0065605)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0084254)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084255)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0084256)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084257)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084258)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084259)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084260)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084261)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084262)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0084263)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084264)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084265)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084266)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084267)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084268)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0084269)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0084270)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0084272)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084273)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084274)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084275)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084276)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084277)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084278)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084279)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084280)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084281)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084282)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084283)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084284)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084285)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084286)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084287)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084288)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084289)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084290)
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 4729.6 | Semi standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 4189.1 | Standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 5308.2 | Standard polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4698.8 | Semi standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4155.1 | Standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4572.0 | Standard polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4949.0 | Semi standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4301.5 | Standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5299.4 | Standard polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 5122.7 | Semi standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4327.1 | Standard non polar | 33892256 | PA(16:1(9Z)/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4671.7 | Standard polar | 33892256 |
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