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 03:01:36 UTC |
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Update Date | 2022-11-30 19:25:57 UTC |
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HMDB ID | HMDB0114899 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:1(11Z)/16:0) |
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Description | PA(18:1(11Z)/16:0) 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(18:1(11Z)/16:0), in particular, consists of one chain of cis-vaccenic acid at the C-1 position and one chain of palmitic 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)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C37H71O8P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h13,15,35H,3-12,14,16-34H2,1-2H3,(H2,40,41,42)/b15-13-/t35-/m1/s1 |
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Synonyms | Value | Source |
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1-cis-vaccenoyl-2-palmitoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-cis-vaccenoyl-2-palmitoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:1/16:0) | SMPDB, HMDB | PA(18:1n7/16:0) | SMPDB, HMDB | PA(18:1w7/16:0) | SMPDB, HMDB | PA(34:1) | SMPDB, HMDB | Phosphatidic acid(18:1(11Z)/16:0) | SMPDB, HMDB | Phosphatidic acid(18:1/16:0) | SMPDB, HMDB | Phosphatidic acid(18:1n7/16:0) | SMPDB, HMDB | Phosphatidic acid(18:1w7/16:0) | SMPDB, HMDB | Phosphatidic acid(34:1) | SMPDB, HMDB | Phosphatidate(18:1(11Z)/16:0) | SMPDB, HMDB | Phosphatidate(18:1/16:0) | SMPDB, HMDB | Phosphatidate(18:1n7/16:0) | SMPDB, HMDB | Phosphatidate(18:1w7/16:0) | SMPDB, HMDB | Phosphatidate(34:1) | SMPDB, HMDB | PA(18:1(11Z)/16:0) | SMPDB | [(2R)-2-(Hexadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C37H71O8P |
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Average Molecular Weight | 674.941 |
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Monoisotopic Molecular Weight | 674.488656244 |
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IUPAC Name | [(2R)-2-(hexadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-(hexadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C37H71O8P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h13,15,35H,3-12,14,16-34H2,1-2H3,(H2,40,41,42)/b15-13-/t35-/m1/s1 |
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InChI Key | MVJLJVFGNPWDHA-JUOLSMOWSA-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 | Not Available |
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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- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0028429)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0028430)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0028431)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0) (PathBank: SMP0069886)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0) (PathBank: SMP0028426)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z)) (PathBank: SMP0028427)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:1(11Z)) (PathBank: SMP0016050)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:1(9Z)) (PathBank: SMP0016051)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:2(9Z,12Z)) (PathBank: SMP0016052)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0016053)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0016054)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:1(11Z)) (PathBank: SMP0021698)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0021699)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:1(13Z)) (PathBank: SMP0021700)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/24:1(15Z)) (PathBank: SMP0021701)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0021702)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:2(13Z,16Z)) (PathBank: SMP0021703)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0021704)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0021705)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0021706)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0021707)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0021708)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021709)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021710)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0) (PathBank: SMP0028416)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028417)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0) (PathBank: SMP0028418)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z)) (PathBank: SMP0028419)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0028420)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0028421)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028422)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028423)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028424)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028425)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028432)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028433)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028434)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028435)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0) (PathBank: SMP0028436)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0028437)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028438)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0028439)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0) (PathBank: SMP0028440)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0028441)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0028442)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028443)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0028444)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0028445)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0028446)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028447)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028448)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028449)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028450)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028451)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028452)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028453)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028454)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028455)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028456)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028457)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:2(11Z,14Z)) (PathBank: SMP0033045)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0033046)
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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(18:1(11Z)/16:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4725.9 | Semi standard non polar | 33892256 | PA(18:1(11Z)/16:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4227.1 | Standard non polar | 33892256 | PA(18:1(11Z)/16:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5655.5 | Standard polar | 33892256 | PA(18:1(11Z)/16:0),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4700.0 | Semi standard non polar | 33892256 | PA(18:1(11Z)/16:0),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4214.3 | Standard non polar | 33892256 | PA(18:1(11Z)/16:0),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4903.5 | Standard polar | 33892256 | PA(18:1(11Z)/16:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4973.1 | Semi standard non polar | 33892256 | PA(18:1(11Z)/16:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4333.0 | Standard non polar | 33892256 | PA(18:1(11Z)/16:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5635.3 | Standard polar | 33892256 |
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