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PS(16:0/16:0) (ECMDB00614) (M2MDB000157)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:27:48 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-12-09 12:10:32 -0700 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | PS(16:0/16:0) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | PS(16:0/16:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. 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. Phosphatidylserines typically carry a net charge of -1 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. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C38H74NO10P | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 735.9686 Monoisotopic: 735.505034105 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | KLFKZIQAIPDJCW-GPOMZPHUSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 3036-82-6 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2S)-2-amino-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dipalmitoyl phosphatidylserine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines 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 | Glycerophosphoserines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Phosphatidylserines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | CDP-1,2-didodecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-dihexadec-9-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-dihexadecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-dioctadec-11-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-Dioctadecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-ditetradec-7-enoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-ditetradecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0) Hydrogen ion + PS(16:0/16:0) > Carbon dioxide + PE(14:0/14:0) CDP-diacylglycerol + L-Serine <> Cytidine monophosphate + PS(16:0/16:0) PS(16:0/16:0) <> PE(14:0/14:0) + Carbon dioxide PS(16:0/16:0) + Water <> 2-Acyl-sn-glycero-3-phosphoserine + Fatty acid CDP-DG(16:0/16:0) + L-Serine + CDP-DG(16:0/16:0) + L-Serine > Hydrogen ion + Cytidine monophosphate + PS(16:0/16:0) + Cytidine monophosphate PS(16:0/16:0) + Hydrogen ion > PE(16:0/16:0) + Carbon dioxide PS(16:0/16:0) + Hydrogen ion > PE(16:0/15:0) + Carbon dioxide PS(16:0/16:0) + Hydrogen ion > PE(15:0/16:0) + Carbon dioxide CDP-diacylglycerol + L-Serine <> Cytidine monophosphate + PS(16:0/16:0) Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0) Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Hermetter, A.; Paltauf, F.; Hauser, H. Synthesis of diacyl and alkylacyl glycerophosphoserines. Chemistry and Physics of Lipids (1982), 30(1), 35-45. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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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 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:
- 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:
- CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
- Gene Name:
- pssA
- Uniprot ID:
- P23830
- Molecular weight:
- 52801
Reactions
CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine. |
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