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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 | PAMDB001848 |
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Identification |
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| Name: |
PG(16:0/18:0) |
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| Description: | PG(16:0/18:0) 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(16:0/18:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. In Pseudomonas aeruginosa 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: | - (2R)-1-(2S)-2,3-dihydroxypropoxy-hydroxyphosphoryloxy-3-hexadecanoyloxypropan-2-yl octadecanoate
- (2R)-1-(2S)-2,3-Dihydroxypropoxy-hydroxyphosphoryloxy-3-hexadecanoyloxypropan-2-yl octadecanoic acid
- 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoglycerol
- 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoglycerol
- GPG(16:0/18:0)
- GPG(34:0)
- PG(34:0)
- Phosphatidylglycerol(16:0/18:0)
- Phosphatidylglycerol(34:0)
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Chemical Formula: |
C40H79O10P |
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| Average Molecular Weight: |
751.023 |
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| Monoisotopic Molecular
Weight: |
750.54108526 |
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| InChI Key: |
WYVBOKLMHDFYQD-QPPIDDCLSA-N |
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| InChI: | InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 |
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| CAS
number: |
Not Available |
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| IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid |
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Traditional IUPAC Name: |
(2S)-2,3-dihydroxypropoxy(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxyphosphinic acid |
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| SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC |
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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
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic phosphate
- Dicarboxylic acid or derivatives
- Saccharide
- Secondary alcohol
- Carboxylic acid ester
- 1,2-diol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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: |
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
- 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
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- 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: |
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