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 03:01:58 UTC |
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Update Date | 2022-11-30 19:25:57 UTC |
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HMDB ID | HMDB0114901 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:1(11Z)/18:0) |
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Description | PA(18:1(11Z)/18:0) 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)/18:0), in particular, consists of one chain of cis-vaccenic acid at the C-1 position and one chain of stearic 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)CCCCCCCCCCCCCCCCC InChI=1S/C39H75O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,37H,3-12,14,16-36H2,1-2H3,(H2,42,43,44)/b15-13-/t37-/m1/s1 |
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Synonyms | Value | Source |
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1-cis-vaccenoyl-2-stearoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-cis-vaccenoyl-2-stearoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:1/18:0) | SMPDB, HMDB | PA(18:1n7/18:0) | SMPDB, HMDB | PA(18:1w7/18:0) | SMPDB, HMDB | PA(36:1) | SMPDB, HMDB | Phosphatidic acid(18:1(11Z)/18:0) | SMPDB, HMDB | Phosphatidic acid(18:1/18:0) | SMPDB, HMDB | Phosphatidic acid(18:1n7/18:0) | SMPDB, HMDB | Phosphatidic acid(18:1w7/18:0) | SMPDB, HMDB | Phosphatidic acid(36:1) | SMPDB, HMDB | Phosphatidate(18:1(11Z)/18:0) | SMPDB, HMDB | Phosphatidate(18:1/18:0) | SMPDB, HMDB | Phosphatidate(18:1n7/18:0) | SMPDB, HMDB | Phosphatidate(18:1w7/18:0) | SMPDB, HMDB | Phosphatidate(36:1) | SMPDB, HMDB | PA(18:1(11Z)/18:0) | SMPDB | [(2R)-3-[(11Z)-Octadec-11-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C39H75O8P |
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Average Molecular Weight | 702.995 |
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Monoisotopic Molecular Weight | 702.519956373 |
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IUPAC Name | [(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(octadecanoyloxy)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)CCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C39H75O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,37H,3-12,14,16-36H2,1-2H3,(H2,42,43,44)/b15-13-/t37-/m1/s1 |
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InChI Key | CHJFGLFFOBSASU-IEHWZJNJSA-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)/18:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0028501)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0028502)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z)) (PathBank: SMP0069959)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:1(11Z)) (PathBank: SMP0016058)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:1(9Z)) (PathBank: SMP0016059)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:2(9Z,12Z)) (PathBank: SMP0016060)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:1(11Z)) (PathBank: SMP0021711)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0021712)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:1(13Z)) (PathBank: SMP0021713)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/24:1(15Z)) (PathBank: SMP0021714)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0021715)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0021716)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:2(13Z,16Z)) (PathBank: SMP0021717)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0021718)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0021719)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0021720)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0021721)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0021722)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0021723)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021724)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021725)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028498)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0) (PathBank: SMP0028499)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028503)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028504)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028505)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028506)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0) (PathBank: SMP0028507)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z)) (PathBank: SMP0028508)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0) (PathBank: SMP0028509)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0028510)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0028511)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0028512)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028513)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028514)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028515)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028516)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0) (PathBank: SMP0028517)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0028518)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028519)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0028520)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0) (PathBank: SMP0028521)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0028522)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0028523)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028524)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0028525)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0028526)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0028527)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028528)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028529)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0028530)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028531)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028532)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028533)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028534)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0028535)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028536)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028537)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028538)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:2(11Z,14Z)) (PathBank: SMP0033049)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0033050)
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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)/18:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 4939.2 | Semi standard non polar | 33892256 | PA(18:1(11Z)/18:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 4396.8 | Standard non polar | 33892256 | PA(18:1(11Z)/18:0),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 5835.4 | Standard polar | 33892256 | PA(18:1(11Z)/18:0),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)CCCCCCCCCCCCCCCCC | 4903.0 | Semi standard non polar | 33892256 | PA(18:1(11Z)/18:0),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)CCCCCCCCCCCCCCCCC | 4382.4 | Standard non polar | 33892256 | PA(18:1(11Z)/18:0),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)CCCCCCCCCCCCCCCCC | 5077.9 | Standard polar | 33892256 | PA(18:1(11Z)/18:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 5184.5 | Semi standard non polar | 33892256 | PA(18:1(11Z)/18:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 4497.4 | Standard non polar | 33892256 | PA(18:1(11Z)/18:0),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC | 5811.3 | Standard polar | 33892256 |
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