Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:57:28 -0600 |
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Update Date | 2015-12-09 12:07:44 -0700 |
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Secondary Accession Numbers | |
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Identification |
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Name: | PG(16:1(9Z)/17:0) |
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Description | PG(16:1(9Z)/17:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:1(9Z)/17:0), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one heptadecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. |
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Structure | |
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Synonyms: | - 1-(9Z-hexadecenoyl)-2-margaroyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-(9Z-hexadecenoyl)-2-margaroyl-sn-glycero-3-phosphoglycerol
- 1-palmitoleoyl-2-heptadecanoyl-sn-glycero-3-phosphoglycerol
- GPG(16:1/17:0)
- GPG(33:1)
- PG(16:1/17:0)
- PG(33:1)
- Phosphatidylglycerol(16:1/17:0)
- Phosphatidylglycerol(33:1)
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Chemical Formula: | C39H75O10P |
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Weight: | Average: 734.9806 Monoisotopic: 734.509785132 |
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InChI Key: | MHNGEXBQDYOSOH-ILKHLXMCSA-N |
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InChI: | InChI=1S/C39H75O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-38(42)46-34-37(35-48-50(44,45)47-33-36(41)32-40)49-39(43)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h14,16,36-37,40-41H,3-13,15,17-35H2,1-2H3,(H,44,45)/b16-14-/t36-,37+/m0/s1 |
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CAS number: | Not Available |
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IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid |
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Traditional IUPAC Name: | (2S)-2,3-dihydroxypropoxy((2R)-3-(heptadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid |
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SMILES: | [H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)CO |
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Chemical Taxonomy |
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Description | 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. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
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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
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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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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SMPDB Pathways: | phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/16:1(9Z))) | PW001446 |    | phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/17:0cycw7c) | PW001440 |    | phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/17:0cycw7c) | PW001564 |    |
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KEGG Pathways: | - Glycerophospholipid metabolism ec00564
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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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
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
- 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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