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 | PAMDB004108 |
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Identification |
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Name: |
PG(19:iso/14:0(3-OH)) |
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Description: | PG(19:iso/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(19:iso/14:0(3-OH)), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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: | - 1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
- 1-17-methylocatdecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
- GPG(19:0/14:0)
- GPG(33:0)
- PG(19:0/14:0)
- PG(33:0)
- Phosphatidylglycerol(19:0/14:0)
- Phosphatidylglycerol(33:0)
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Chemical Formula: |
C39H77O11P |
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Average Molecular Weight: |
752.9958 |
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Monoisotopic Molecular
Weight: |
752.520349818 |
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InChI Key: |
YWSQPWCEOLJTJR-UHFFFAOYSA-N |
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InChI: | InChI=1S/C39H77O11P/c1-4-5-6-7-8-14-18-21-24-27-35(41)29-39(44)50-37(33-49-51(45,46)48-31-36(42)30-40)32-47-38(43)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3/h34-37,40-42H,4-33H2,1-3H3,(H,45,46) |
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CAS
number: |
Not Available |
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IUPAC Name: | (2,3-dihydroxypropoxy)({2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid |
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Traditional IUPAC Name: |
2,3-dihydroxypropoxy(2-[(3-hydroxytetradecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid |
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SMILES: | CCCCCCCCCCCC(O)CC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)CO |
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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
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Hydroxy acid
- Phosphoric acid ester
- Organic phosphate
- Organic phosphoric acid derivative
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxide
- Primary 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: |
- Casadei MA, Ma?as 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
- 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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