Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-10-29 15:03:29 UTC |
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Update Date | 2022-11-30 19:03:55 UTC |
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HMDB ID | HMDB0011158 |
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Secondary Accession Numbers | - HMDB0011338
- HMDB11158
- HMDB11338
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Metabolite Identification |
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Common Name | PE(P-16:0/16:0) |
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Description | 2-Hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an intermediate of ether lipid metabolism. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. In the ether lipid metabolism pathway, 2-hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is involved in two enzymatic reactions: 1. It irreversibly produces 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase A2 (EC:3.1.1.4) and 2. it irreversibly produces 2-hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate via the enzyme phospholipase D (EC:3.1.4.4). While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. |
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Structure | [H][C@@](CO\C=C/CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C37H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-32-42-34-36(35-44-46(40,41)43-33-31-38)45-37(39)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32,36H,3-28,30-31,33-35,38H2,1-2H3,(H,40,41)/b32-29-/t36-/m1/s1 |
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Synonyms | Value | Source |
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1-(Hexadec-1-enyl)-2-palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion | ChEBI | 1-[(1Z)-Hexadec-1-enyl]-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion | ChEBI | 1-[(1Z)-Hexadec-1-enyl]-2-palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion | ChEBI | 2-Hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine | HMDB | 1-(1Z-Hexadecenyl)-2-palmitoyl-sn-glycero-3-phosphoethanolamine | HMDB | 1-(1Z-Hexadecenyl)-2-palmitoyl-sn-glycero-phosphatidylethanolamine | HMDB | GPE(16:1/16:0) | HMDB | GPE(32:1) | HMDB | GPE(O-16:1(1Z)/16:0) | HMDB | GPE(p-16:0/16:0) | HMDB | GPEtn(16:1/16:0) | HMDB | GPEtn(32:1) | HMDB | GPEtn(O-16:1(1Z)/16:0) | HMDB | GPEtn(p-16:0/16:0) | HMDB | PE(16:1/16:0) | HMDB | PE(32:1) | HMDB | PE(O-16:1(1Z)/16:0) | HMDB | Phosphatidylethanolamine(16:1/16:0) | HMDB | Phosphatidylethanolamine(32:1) | HMDB | Phosphatidylethanolamine(O-16:1(1Z)/16:0) | HMDB | Phosphatidylethanolamine(p-16:0/16:0) | HMDB | PE(P-16:0/16:0) | ChEBI |
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Chemical Formula | C37H74NO7P |
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Average Molecular Weight | 675.9597 |
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Monoisotopic Molecular Weight | 675.520290239 |
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IUPAC Name | (2-aminoethoxy)[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-(hexadecanoyloxy)propoxy]phosphinic acid |
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Traditional Name | 2-aminoethoxy((2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-(hexadecanoyloxy)propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](CO\C=C/CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C37H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-32-42-34-36(35-44-46(40,41)43-33-31-38)45-37(39)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32,36H,3-28,30-31,33-35,38H2,1-2H3,(H,40,41)/b32-29-/t36-/m1/s1 |
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InChI Key | FDULCEKAOVWBTQ-PXOIRPRXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position. |
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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 | Glycerophosphoethanolamines |
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Direct Parent | 1-(1Z-alkenyl),2-acylglycerophosphoethanolamines |
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Alternative Parents | |
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Substituents | - 1-(1z-alkenyl),2-acylglycerophosphoethanolamine
- Glycerol vinyl ether
- Phosphoethanolamine
- Fatty acid ester
- Dialkyl phosphate
- Fatty acyl
- Alkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Amino acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary amine
- Primary aliphatic amine
- Organic oxygen compound
- Amine
- Carbonyl group
- Organopnictogen compound
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | - 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamine (CHEBI:72803 )
- 1-(1Z-alkenyl),2-acylglycerophosphoethanolamines (LMGP02030013 )
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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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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PE(P-16:0/16:0),1TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4738.9 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),1TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4249.5 | Standard non polar | 33892256 | PE(P-16:0/16:0),1TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 6331.1 | Standard polar | 33892256 | PE(P-16:0/16:0),1TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4788.9 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),1TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4412.6 | Standard non polar | 33892256 | PE(P-16:0/16:0),1TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 6183.3 | Standard polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4716.7 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4355.6 | Standard non polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5165.1 | Standard polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5018.0 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4392.3 | Standard non polar | 33892256 | PE(P-16:0/16:0),2TMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5833.3 | Standard polar | 33892256 | PE(P-16:0/16:0),3TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5014.2 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),3TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4342.0 | Standard non polar | 33892256 | PE(P-16:0/16:0),3TMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4981.7 | Standard polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4975.5 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4322.2 | Standard non polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 6283.2 | Standard polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5023.8 | Semi standard non polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4494.7 | Standard non polar | 33892256 | PE(P-16:0/16:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 6065.8 | Standard polar | 33892256 |
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