Record Information |
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Version | 2.0 |
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Creation Date | 2012-10-24 09:55:01 -0600 |
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Update Date | 2015-09-16 17:34:54 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | PG(15:0cyclo/19:iso) |
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Description | PG(15:0cyclo/19:iso) 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(15:0cyclo/19:iso), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to the C-1 atom, and one 17-methylocatdecanoyl 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-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
- 1-(cis-9,10-Methylenetetradecanoyl)-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol
- GPG(15:0/19:0)
- GPG(34:0)
- PG(15:0/19:0)
- PG(34:0)
- Phosphatidylglycerol(15:0/19:0)
- Phosphatidylglycerol(34:0)
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Chemical Formula: | C40H77O10P |
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Weight: | Average: 749.0071 Monoisotopic: 748.525435196 |
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InChI Key: | ZGAFCCPBGJRBLI-UHFFFAOYSA-N |
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InChI: | InChI=1S/C40H77O10P/c1-4-5-25-35-29-36(35)26-21-17-15-19-22-27-39(43)47-32-38(33-49-51(45,46)48-31-37(42)30-41)50-40(44)28-23-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-38,41-42H,4-33H2,1-3H3,(H,45,46) |
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CAS number: | Not Available |
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IUPAC Name: | (3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy)(2,3-dihydroxypropoxy)phosphinic acid |
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Traditional IUPAC Name: | 3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy(2,3-dihydroxypropoxy)phosphinic acid |
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SMILES: | CCCCC1CC1CCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)C |
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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
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid ester
- 1,2-diol
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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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SMPDB Pathways: | phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/15:0cyclo/19:0cycv8c)) | PW001517 | | phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo) | PW001088 | |
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KEGG Pathways: | - Glycerophospholipid metabolism ec00564
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EcoCyc Pathways: | Not Available |
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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: | - Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
- 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
- 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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