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PG(12:0/12:0) (ECMDB21265) (M2MDB001672)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-07-30 14:55:10 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-12-09 12:06:33 -0700 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | PG(12:0/12:0) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | PG(12:0/12:0) 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(12:0/12:0), in particular, consists of two dodecanoyl chains at positions C-1 and C-2. 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: |
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Chemical Formula: | C30H59O10P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 610.766 Monoisotopic: 610.384585098 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | LHCZDUCPSRJDJT-WUFINQPMSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C30H59O10P/c1-3-5-7-9-11-13-15-17-19-21-29(33)37-25-28(26-39-41(35,36)38-24-27(32)23-31)40-30(34)22-20-18-16-14-12-10-8-6-4-2/h27-28,31-32H,3-26H2,1-2H3,(H,35,36)/t27-,28+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [(2R)-2,3-bis(dodecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dilauroyl phosphatidylglycerol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Membrane | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Water + PGP(12:0/12:0) > PG(12:0/12:0) + Phosphate 2 PG(12:0/12:0) <> cardiolipin (tetradodecanoyl, n-C12:0) + Glycerol Adenosine triphosphate + Water + PG(12:0/12:0) > ADP + Hydrogen ion + Phosphate + PG(12:0/12:0) Adenosine triphosphate + Water + PG(12:0/12:0) > ADP + Hydrogen ion + Phosphate + PG(12:0/12:0) 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PG(12:0/12:0) + Pyrophosphate Water + PG(12:0/12:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion Water + PG(12:0/12:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerophosphoglycerol 2 PGP(12:0/12:0) + Water >2 PG(12:0/12:0) + Phosphate PG(12:0/12:0) + PE(12:0(3-OH)/12:0(3-OH)) > Ethanolamine + CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0) PE(12:0(3-OH)/12:0) + PG(12:0/12:0) > Ethanolamine + CL(12:0(3-OH)/12:0/12:0/12:0) PE(12:0(3-OH)/17:0cycw7c) + PG(12:0/12:0) > Ethanolamine + CL(12:0(3-OH)/17:0cycw7c/12:0/12:0) PE(12:0/12:0(3-OH)) + PG(12:0/12:0) > Ethanolamine + CL(12:0/12:0(3-OH)/12:0/12:0) PE(12:0/17:0cycw7c) + PG(12:0/12:0) Ethanolamine + CL(12:0/17:0cycw7c/12:0/12:0) PG(12:0/12:0) + PE(16:0/12:0) > Ethanolamine + CL(16:0/12:0/12:0/12:0) PE(16:1(9Z)/12:0) + PG(12:0/12:0) > CL(16:1(9Z)/12:0/12:0/12:0) + Ethanolamine 2 PG(12:0/12:0) > Glycerol + cardiolipin (tetradodecanoyl, n-C12:0) PE(17:0cycw7c/12:0) + PG(12:0/12:0) > Ethanolamine + CL(17:0cycw7c/12:0/12:0/12:0) PG(12:0/12:0) + PE(18:0/12:0) > Ethanolamine + CL(18:0/12:0/12:0/12:0) PE(18:1(11Z)/12:0) + PG(12:0/12:0) > Ethanolamine + CL(18:1(11Z)/12:0/12:0/12:0) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Lipid transport and metabolism
- Specific function:
- 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
- Gene Name:
- pldB
- Uniprot ID:
- P07000
- Molecular weight:
- 38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate. |
- General function:
- Involved in phospholipase activity
- Specific function:
- Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
- Gene Name:
- pldA
- Uniprot ID:
- P0A921
- Molecular weight:
- 33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate. |
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
- Gene Name:
- pgpB
- Uniprot ID:
- P0A924
- Molecular weight:
- 29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate. |
- General function:
- Involved in phosphatidylglycerophosphatase activity
- Specific function:
- One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
- Gene Name:
- pgpA
- Uniprot ID:
- P18200
- Molecular weight:
- 19418
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate. |
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
- Gene Name:
- aas
- Uniprot ID:
- P31119
- Molecular weight:
- 80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine. |
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein]. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
- Gene Name:
- msbA
- Uniprot ID:
- P60752
- Molecular weight:
- 64460
- General function:
- Involved in phosphotransferase activity, for other substituted phosphate groups
- Specific function:
- Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
- Gene Name:
- cls
- Uniprot ID:
- P0A6H8
- Molecular weight:
- 54822
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
- Gene Name:
- ybhO
- Uniprot ID:
- P0AA84
- Molecular weight:
- 47633
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol. |
- General function:
- cardiolipin biosynthetic process
- Specific function:
- Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
- Gene Name:
- clsC
- Uniprot ID:
- P75919
- Molecular weight:
- 53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine |
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
- Gene Name:
- msbA
- Uniprot ID:
- P60752
- Molecular weight:
- 64460