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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB003945 |
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Identification |
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| Name: |
PS(12:0(3-OH)/12:0) |
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| Description: | PS(12:0(3-OH)/12:0) 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 atoms.. PS(12:0(3-OH)/12:0), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one dodecanoyl to the C-2 atom. 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. |
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Structure |
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| Synonyms: | - 1-3-hydroxydodecanoyl-2-dodecanoyl-sn-glycero-3-phosphoserine
- 1-3-hydroxydodecanoyl-2-dodecanoyl-sn-glycero-3-phosphoserine
- Phosphatidylserine(12:0/12:0)
- Phosphatidylserine(24:0)
- PS(12:0/12:0)
- PS(24:0)
- PSer(12:0/12:0)
- PSer(24:0)
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Chemical Formula: |
C30H58NO11P |
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| Average Molecular Weight: |
639.764 |
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| Monoisotopic Molecular
Weight: |
639.37474869 |
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| InChI Key: |
SQEAWEIJTXKVBO-LVSLPKHJSA-N |
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| InChI: | InChI=1S/C30H58NO11P/c1-3-5-7-9-11-12-14-16-18-20-28(33)42-26(23-40-43(37,38)41-24-27(31)30(35)36)22-39-29(34)21-25(32)19-17-15-13-10-8-6-4-2/h25-27,32H,3-24,31H2,1-2H3,(H,35,36)(H,37,38)/t25?,26-,27+/m1/s1 |
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| CAS
number: |
Not Available |
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| IUPAC Name: | (2S)-2-amino-3-({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid |
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Traditional IUPAC Name: |
(2S)-2-amino-3-{[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid |
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| SMILES: | [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCCC)C(O)=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound 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. |
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Kingdom |
Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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Class |
Glycerophospholipids |
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| Sub Class | Glycerophosphoserines |
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Direct Parent |
Phosphatidylserines |
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| Alternative Parents |
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| Substituents |
- Diacyl-glycerol-3-phosphoserine
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Tricarboxylic acid or derivatives
- Phosphoethanolamine
- Fatty acid ester
- Beta-hydroxy acid
- Dialkyl phosphate
- Hydroxy acid
- Phosphoric acid ester
- Alkyl phosphate
- Organic phosphoric acid derivative
- Fatty acyl
- Secondary alcohol
- Carboxylic acid ester
- Amino acid
- Amino acid or derivatives
- Carboxylic acid derivative
- Carboxylic acid
- Organooxygen compound
- Primary amine
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Primary aliphatic amine
- Aliphatic acyclic compound
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| Molecular Framework |
Aliphatic acyclic compounds |
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| External Descriptors |
Not Available |
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Physical Properties |
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| State: |
Solid |
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| Charge: | -1 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Membrane |
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| Reactions: | |
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Pathways: |
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Spectra |
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| Spectra: |
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References |
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| 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
- Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. Pubmed: 4902888
- 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
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
| Resource | Link |
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| 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 |
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