| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 01:32:09 UTC |
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| Update date | 2015-07-21 06:59:17 UTC |
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| Primary ID | FDB027930 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | PA(P-16:0e/18:2(9Z,12Z)) |
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| Description | 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate 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.
2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl))-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase D (EC: 3.1.4.4).
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. [HMDB] |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C37H69O7P |
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| IUPAC name | [(2R)-3-(hexadec-1-en-1-yloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphonic acid |
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| InChI Identifier | InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1 |
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| InChI Key | OLCTYLMZTXKGKH-PSXMRANNSA-N |
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| Isomeric SMILES | [H][C@@](COC=CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCC=CCCCCC |
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| Average Molecular Weight | 656.9133 |
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| Monoisotopic Molecular Weight | 656.478091074 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphates. These are glycerophosphates 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 | Glycerophosphates |
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| Direct Parent | 1-(1Z-alkenyl),2-acyl-glycerophosphates |
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| Alternative Parents | |
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| Substituents | - 1-(1z-alkenyl),2-acyl-glycerol-3-phosphate
- Glycerol vinyl ether
- Monoalkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 24766521 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C15647 |
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| Pubchem Compound ID | 52929743 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB11155 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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