| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-10-24 09:54:59 -0600 |
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| Update Date | 2015-12-09 12:06:50 -0700 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | PG(14:0(3-OH)/17:0cycw7c) |
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| Description | PG(14:0(3-OH)/17:0cycw7c) 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(14:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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: | - 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phospho-(1'-glycerol)
- 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol
- 1-3-hydroxytetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoglycerol
- GPG(14:0/17:0)
- GPG(31:0)
- PG(14:0/17:0)
- PG(31:0)
- Phosphatidylglycerol(14:0/17:0)
- Phosphatidylglycerol(31:0)
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| Chemical Formula: | C37H71O11P |
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| Weight: | Average: 722.938
Monoisotopic: 722.473400104 |
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| InChI Key: | NCFDTLKDDWOMGW-BISNVOBLSA-N |
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| InChI: | InChI=1S/C37H71O11P/c1-3-5-7-9-10-11-12-15-19-23-33(39)26-37(42)48-35(30-47-49(43,44)46-28-34(40)27-38)29-45-36(41)24-20-16-13-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34-,35+/m0/s1 |
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| CAS number: | Not Available |
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| IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid |
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| Traditional IUPAC Name: | (2S)-2,3-dihydroxypropoxy((2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid |
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| SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CC(O)CCCCCCCCCCC |
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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 homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic 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(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c)) | PW001941 |    | | phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0/14:0)) | PW001942 |    |
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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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