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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB002030 |
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Identification |
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| Name: |
PG(15:0/16:1) |
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| Description: | PG(15:0/16:1) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(15:0/16:1), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. |
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Structure |
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| Synonyms: | - 1-pentadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
- 1-pentadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol
- 1-pentadecanoyl-2-animal fats and vegetable oils-sn-glycero-3-phospho-(1'-glycerol)
- 1-pentadecanoyl-2-animal fats and vegetable oils-sn-glycero-3-phosphoglycerol
- 1-pentadecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol
- GPG(15:0/16:1)
- GPG(31:1)
- PG(31:1)
- Phosphatidylglycerol(15:0/16:1)
- Phosphatidylglycerol(31:1)
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Chemical Formula: |
C37H71O10P |
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| Average Molecular Weight: |
706.9274 |
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| Monoisotopic Molecular
Weight: |
706.478485004 |
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| InChI Key: |
XINYTKIWPKLZAT-SQFISAMPSA-N |
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| InChI: | InChI=1S/C37H71O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)47-35(33-46-48(42,43)45-31-34(39)30-38)32-44-36(40)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,34-35,38-39H,3-12,14,16-33H2,1-2H3,(H,42,43)/b15-13- |
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| CAS
number: |
Not Available |
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| IUPAC Name: | (2,3-dihydroxypropoxy)({2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy})phosphinic acid |
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Traditional IUPAC Name: |
2,3-dihydroxypropoxy(2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid |
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| SMILES: | CCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C/CCCCCC |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety 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 | Glycerophosphoglycerols |
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Direct Parent |
Phosphatidylglycerols |
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| Alternative Parents |
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| Substituents |
- 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Organic phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Primary alcohol
- 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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Physical Properties |
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| State: |
Solid |
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| Charge: | -1 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Membrane |
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| Reactions: |
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Pathways: |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
| Resource | Link |
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| CHEBI ID | Not Available | | HMDB ID | Not Available | | Pubchem Compound ID | Not Available | | Kegg ID | Not Available | | ChemSpider ID | Not Available | | Wikipedia ID | Not Available | | BioCyc ID | Not Available |
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