Record Information |
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Version | 2.0 |
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Creation Date | 2012-10-24 09:55:00 -0600 |
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Update Date | 2015-12-09 12:07:12 -0700 |
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Secondary Accession Numbers | |
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Identification |
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Name: | PG(15:0/14:0(3-OH)) |
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Description | PG(15:0/14:0(3-OH)) 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(15:0/14:0(3-OH)), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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-pentadecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-pentadecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
- 1-pentadecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
- GPG(15:0/14:0)
- GPG(29:0)
- PG(15:0/14:0)
- PG(29:0)
- Phosphatidylglycerol(15:0/14:0)
- Phosphatidylglycerol(29:0)
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Chemical Formula: | C35H69O11P |
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Weight: | Average: 696.9 Monoisotopic: 696.45775004 |
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InChI Key: | WXFQQKIGOUHPGL-ADIDXWPESA-N |
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InChI: | InChI=1S/C35H69O11P/c1-3-5-7-9-11-13-14-15-17-19-21-23-25-34(39)46-33(30-45-47(41,42)44-28-32(38)27-36)29-43-35(40)26-31(37)24-22-20-18-16-12-10-8-6-4-2/h31-33,36-38H,3-30H2,1-2H3,(H,41,42)/t31?,32-,33+/m0/s1 |
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CAS number: | Not Available |
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IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphinic acid |
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Traditional IUPAC Name: | (2S)-2,3-dihydroxypropoxy((2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(pentadecanoyloxy)propoxy)phosphinic acid |
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SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC |
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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. |
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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
- Beta-hydroxy acid
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Dicarboxylic acid or derivatives
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Hydroxy acid
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- 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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SMPDB Pathways: | phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/15:0cyclo/14:0)) | PW001292 |    | phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/15:0cyclo)) | PW001433 |    | phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/19:0cycv8c) | PW001062 |    | phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/14:0) | PW001081 |    | phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/14:0) | PW001087 |    | phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/14:0/15:0cyclo) | PW001159 |    | phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/14:0) | PW001161 |    | phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/14:0) | PW001654 |    |
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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: | - 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
- Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 Pubmed: 22753057
- 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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