| Record Information |
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| Version | 2.0 |
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| Creation Date | 2015-09-08 19:32:36 -0600 |
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| Update Date | 2015-12-09 17:18:35 -0700 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | PGP(12:0(3-OH)/16:1(9Z)) |
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| Description | PGP(12:0(3-OH)/16:1(9Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(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 E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase. |
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| Structure | |
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| Synonyms: | Not Available |
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| Chemical Formula: | C34H66O14P2 |
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| Weight: | Average: 760.836
Monoisotopic: 760.392780801 |
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| InChI Key: | GJADBVNIWPYXGP-LGZFZSLRSA-N |
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| InChI: | InChI=1S/C34H66O14P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(37)48-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)28-44-34(38)25-30(35)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-36H,3-11,14-29H2,1-2H3,(H,42,43)(H2,39,40,41)/b13-12-/t30?,31-,32-/m1/s1 |
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| CAS number: | Not Available |
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| IUPAC Name: | [(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid |
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| Traditional IUPAC Name: | (2R)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid |
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| SMILES: | [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates 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 | Glycerophosphoglycerophosphates |
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| Direct Parent | Phosphatidylglycerophosphates |
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| Alternative Parents | |
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| Substituents | - Diacylglycerophosphoglycerophosphate
- Sn-glycerol-3-phosphate
- Beta-hydroxy acid
- Fatty acid ester
- Dialkyl phosphate
- Monoalkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Hydroxy acid
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- 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: | Not Available |
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| Charge: | -3 |
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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(16:1(9Z)/12:0/12:0/12:0)) | PW001955 |    |
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| KEGG Pathways: | Not Available |
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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: | - 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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