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 03:45:11 UTC |
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Update Date | 2022-11-30 19:26:04 UTC |
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HMDB ID | HMDB0115151 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) |
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Description | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 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(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of oleic 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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C41H71O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11,13,17-19,21-23,27,29,39H,3-10,12,14-16,20,24-26,28,30-38H2,1-2H3,(H2,44,45,46)/b13-11-,19-17-,21-18-,23-22-,29-27-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate | ChEBI | 1-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate | ChEBI | 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycero-3-phosphate | ChEBI | 1-C20:4(Omega-6)-2-C18:1(omega-9)-phosphatidylic acid | ChEBI | 1-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoric acid | Generator | 1-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoric acid | Generator | 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycero-3-phosphoric acid | Generator | 1-C20:4(Omega-6)-2-C18:1(omega-9)-phosphatidylate | Generator | 1-Arachidonoyl-2-oleoyl-sn-glycero-3-phosphate | HMDB | 1-Arachidonoyl-2-oleoyl-sn-phosphatidic acid | HMDB | PA(20:4/18:1) | HMDB | PA(20:4N6/18:1N9) | HMDB | PA(20:4W6/18:1W9) | HMDB | PA(38:5) | HMDB | Phosphatidic acid(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) | HMDB | Phosphatidic acid(20:4/18:1) | HMDB | Phosphatidic acid(20:4n6/18:1n9) | HMDB | Phosphatidic acid(20:4W6/18:1W9) | HMDB | Phosphatidic acid(38:5) | HMDB | Phosphatidate(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) | HMDB | Phosphatidate(20:4/18:1) | HMDB | Phosphatidate(20:4N6/18:1N9) | HMDB | Phosphatidate(20:4W6/18:1W9) | HMDB | Phosphatidate(38:5) | HMDB | 1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-arachidonoyl-2-oleoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:4/18:1) | SMPDB, HMDB | PA(20:4n6/18:1n9) | SMPDB, HMDB | PA(20:4w6/18:1w9) | SMPDB, HMDB | PA(38:5) | SMPDB, HMDB | Phosphatidic acid(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) | SMPDB, HMDB | Phosphatidic acid(20:4/18:1) | SMPDB, HMDB | Phosphatidic acid(20:4n6/18:1n9) | SMPDB, HMDB | Phosphatidic acid(20:4w6/18:1w9) | SMPDB, HMDB | Phosphatidic acid(38:5) | SMPDB, HMDB | Phosphatidate(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) | SMPDB, HMDB | Phosphatidate(20:4/18:1) | SMPDB, HMDB | Phosphatidate(20:4n6/18:1n9) | SMPDB, HMDB | Phosphatidate(20:4w6/18:1w9) | SMPDB, HMDB | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) | SMPDB |
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Chemical Formula | C41H71O8P |
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Average Molecular Weight | 722.985 |
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Monoisotopic Molecular Weight | 722.488656244 |
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IUPAC Name | [(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C41H71O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11,13,17-19,21-23,27,29,39H,3-10,12,14-16,20,24-26,28,30-38H2,1-2H3,(H2,44,45,46)/b13-11-,19-17-,21-18-,23-22-,29-27-/t39-/m1/s1 |
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InChI Key | WPZWVFHOVBEOOI-RQOUDQJUSA-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 | |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0072077)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0072078)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0072079)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0072088)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0072090)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0072094)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0079862)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0079863)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0079865)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0079870)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0095134)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0072076)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072080)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0072085)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0072087)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0072089)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072095)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0095133)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0095145)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0072092)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0016136)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0016137)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0016138)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0016139)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024816)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:2(13Z,16Z)) (PathBank: SMP0024817)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024818)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024819)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024820)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024821)
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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 | | Show more...
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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(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5129.3 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 4528.7 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5511.0 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5111.2 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 4493.2 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 4801.6 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5350.4 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 4636.1 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5504.4 | Standard polar | 33892256 |
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