PE(17:0cycw7c/14:0(3-OH)) (ECMDB23511) (M2MDB003901)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-10-24 09:54:30 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-14 11:19:53 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | PE(17:0cycw7c/14:0(3-OH)) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | PE(17:0cycw7c/14:0(3-OH)) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(17:0cycw7c/14:0(3-OH)), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula: | C36H70NO9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 691.9161 Monoisotopic: 691.478819355 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | RPPBWGKLBZHOGU-NQLXYCMNSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C36H70NO9P/c1-3-5-7-9-10-11-12-15-19-23-33(38)28-36(40)46-34(30-45-47(41,42)44-26-25-37)29-43-35(39)24-20-16-13-14-18-22-32-27-31(32)21-17-8-6-4-2/h31-34,38H,3-30,37H2,1-2H3,(H,41,42)/t31?,32?,33?,34-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2-aminoethoxy)[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | 2-aminoethoxy((2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | CCCCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCCCC)COP(O)(=O)OCCN | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Lipids and lipid-like molecules | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Glycerophospholipids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Glycerophosphoethanolamines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Phosphatidylethanolamines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Framework | Aliphatic homomonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Membrane | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | PS(17:0cycw7c/14:0(3-OH)) + Hydrogen ion > PE(17:0cycw7c/14:0(3-OH)) + Carbon dioxide PG(18:1(9Z)/18:1(9Z)) + PE(17:0cycw7c/14:0(3-OH)) > Ethanolamine + CL(18:1(9Z)/17:0cycw7c/18:1(9Z)/14:0) PE(17:0cycw7c/14:0(3-OH)) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/17:0cycw7c/14:0/18:1(9Z)) PG(19:0cycv8c/14:0(3-OH)) + PE(17:0cycw7c/14:0(3-OH)) > Ethanolamine + CL(19:0cycv8c/14:0/17:0cycw7c/14:0) PG(16:1(9Z)/16:1(9Z)) + PE(17:0cycw7c/14:0(3-OH)) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/16:1(9Z)/14:0) PE(17:0cycw7c/14:0(3-OH)) + PG(18:1(9Z)/14:0(3-OH)) > Ethanolamine + CL(17:0cycw7c/18:1(9Z)/14:0/14:0) PG(18:1(9Z)/18:1(9Z)) + PE(17:0cycw7c/14:0(3-OH)) > Ethanolamine + CL(17:0cycw7c/18:1(9Z)/14:0/18:1(9Z)) PE(17:0cycw7c/14:0(3-OH)) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/14:0) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Involved in phosphatidylserine decarboxylase activity
- Specific function:
- Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
- Gene Name:
- psd
- Uniprot ID:
- P0A8K1
- Molecular weight:
- 35934
Reactions
| Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2). |
- 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:
- 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:
- 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