PG(16:1(9Z)/16:0) (ECMDB10585) (M2MDB000794)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 14:18:58 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-12-09 12:07:43 -0700 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | PG(16:1(9Z)/16:0) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | PG(16:1(9Z)/16:0) 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(16:1(9Z)/16:0), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one hexadecanoyl 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: |
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| Chemical Formula: | C38H73O10P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 720.954 Monoisotopic: 720.494135068 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | NOFOTAHTYLXZNV-DCQLZOMZSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C38H73O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,35-36,39-40H,3-13,15,17-34H2,1-2H3,(H,43,44)/b16-14-/t35-,36+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy]phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | (2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy)phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | PGP(16:1(9Z)/16:0) + Water > PG(16:1(9Z)/16:0) + Phosphate PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/16:0) > Ethanolamine + CL(16:0/16:1(9Z)/17:0cycw7c/17:0cycw7c) PE(19:iso/19:iso) + PG(16:1(9Z)/16:0) > CL(16:0/16:1(9Z)/19:0cycv8c/19:0cycv8c) + Ethanolamine PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/16:0) > CL(16:0/17:0cycw7c/16:1(9Z)/17:0cycw7c) + Ethanolamine PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/16:0) > Ethanolamine + CL(16:0/17:0cycw7c/17:0cycw7c/16:1(9Z)) PG(16:1(9Z)/16:0) + PE(19:iso/19:iso) > Ethanolamine + CL(16:0/19:0cycv8c/16:1(9Z)/19:0cycv8c) PE(17:0cycw7c/17:0cycw7c) + PG(16:1(9Z)/16:0) > Ethanolamine + CL(16:1(9Z)/16:0/17:0cycw7c/17:0cycw7c) PE(19:iso/19:iso) + PG(16:1(9Z)/16:0) > Ethanolamine + CL(16:1(9Z)/16:0/19:0cycv8c/16:1(9Z)) PG(16:1(9Z)/16:0) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/16:0/16:1(9Z)/17:0cycw7c) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: |
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| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- 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:
- Not Available
- Specific function:
- Not known; overproduction leads to camphor resistance and chromosome condensation
- Gene Name:
- crcA
- Uniprot ID:
- P37001
- Molecular weight:
- 21770
- 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 phospholipid transporter activity
- Specific function:
- Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
- Gene Name:
- mlaB
- Uniprot ID:
- P64602
- Molecular weight:
- 10680
- General function:
- Secondary metabolites biosynthesis, transport and catabolism
- Specific function:
- Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
- Gene Name:
- mlaD
- Uniprot ID:
- P64604
- Molecular weight:
- 19576
- General function:
- Secondary metabolites biosynthesis, transport and catabolism
- Specific function:
- Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
- Gene Name:
- mlaE
- Uniprot ID:
- P64606
- Molecular weight:
- 27863