Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2012-05-31 14:57:18 -0600 |
---|
Update Date | 2015-12-09 17:01:09 -0700 |
---|
Secondary Accession Numbers | |
---|
Identification |
---|
Name: | PG(17:0/16:1(9Z)) |
---|
Description | PG(17:0/16:1(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(17:0/16:1(9Z)), in particular, consists of one heptadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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. |
---|
Structure | |
---|
Synonyms: | - 1-heptadecanoyl-2-(9Z-hexadecenoyl)-glycero-3-phospho-(1'-sn-glycerol)
- 1-heptadecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol
- 1-margaroyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
- 1-margaroyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol
- GPG(17:0/16:1)
- GPG(33:1)
- PG(17:0/16:1)
- PG(33:1)
- Phosphatidylglycerol(17:0/16:1)
- Phosphatidylglycerol(33:1)
|
---|
Chemical Formula: | C39H75O10P |
---|
Weight: | Average: 734.993 Monoisotopic: 734.509785613 |
---|
InChI Key: | NCKDJCYZMBDFNM-OAQISMCJSA-N |
---|
InChI: | InChI=1S/C39H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-39(43)49-37(35-48-50(44,45)47-33-36(41)32-40)34-46-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,36-37,40-41H,3-13,15,17-35H2,1-2H3,(H,44,45)/b16-14-/t36-,37-/m1/s1 |
---|
CAS number: | Not Available |
---|
IUPAC Name: | [(2R)-2,3-dihydroxypropoxy][(2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid |
---|
Traditional IUPAC Name: | (2R)-2,3-dihydroxypropoxy((2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid |
---|
SMILES: | [H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCC |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphoglycerols |
---|
Direct Parent | Phosphatidylglycerols |
---|
Alternative Parents | |
---|
Substituents | - 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State: | Not Available |
---|
Charge: | -1 |
---|
Melting point: | Not Available |
---|
Experimental Properties: | |
---|
Predicted Properties | |
---|
Biological Properties |
---|
Cellular Locations: | Membrane |
---|
Reactions: | |
---|
SMPDB Pathways: | phospholipid biosynthesis (CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/17:0cycw7c)) | PW001697 |    |
|
---|
KEGG Pathways: | - Glycerophospholipid metabolism ec00564
|
---|
EcoCyc Pathways: | |
---|
Concentrations |
---|
| Not Available |
---|
Spectra |
---|
Spectra: | |
---|
References |
---|
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
- Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
- 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
|
---|
Synthesis Reference: | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
Links |
---|
External Links: | Resource | Link |
---|
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 |
|
---|