Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB004048 |
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Identification |
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Name: |
PG(12:0(3-OH)/16:1(9Z)) |
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Description: | PG(12:0(3-OH)/16:1(9Z)) 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(12:0(3-OH)/16:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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: | - 1-3-hydroxydodecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
- 1-3-hydroxydodecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol
- 1-3-hydroxydodecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol
- GPG(12:0/16:1)
- GPG(28:1)
- PG(12:0/16:1)
- PG(28:1)
- Phosphatidylglycerol(12:0/16:1)
- Phosphatidylglycerol(28:1)
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Chemical Formula: |
C34H65O11P |
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Average Molecular Weight: |
680.857 |
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Monoisotopic Molecular
Weight: |
680.426449911 |
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InChI Key: |
DFZQHYFLUGBZKY-KVRHGVBDSA-N |
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InChI: | InChI=1S/C34H65O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)42-28-32(29-44-46(40,41)43-27-31(37)26-35)45-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-37H,3-11,14-29H2,1-2H3,(H,40,41)/b13-12-/t30?,31-,32+/m0/s1 |
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CAS
number: |
Not Available |
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IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid |
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Traditional IUPAC Name: |
(2S)-2,3-dihydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid |
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SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC(O)CCCCCCCCC |
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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
- 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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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
- Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. Pubmed: 4902888
- 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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