Showing metabocard for PS(14:1(11Z)/14:1(11Z)) (MMDBc0047226)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:15:04 UTC
Update Date2022-09-01 01:42:46 UTC
Metabolite IDMMDBc0047226
Metabolite Identification
Common NamePS(14:1(11Z)/14:1(11Z))
DescriptionPS(14:1(11Z)/14:1(11Z)) 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(14:1(11Z)/14:1(11Z)), in particular, consists of two 11Z-tetradecenoyl 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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f124191fd20>

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3D MOL for #<Metabolite:0x00007f124191fd20>

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3D SDF for #<Metabolite:0x00007f124191fd20>

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3D-SDF for #<Metabolite:0x00007f124191fd20>

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PDB for #<Metabolite:0x00007f124191fd20>

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3D PDB for #<Metabolite:0x00007f124191fd20>

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SMILES for #<Metabolite:0x00007f124191fd20>

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INCHI for #<Metabolite:0x00007f124191fd20>

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SynonymsNot Available
Molecular FormulaC34H62NO10P
Average Mass675.841
Monoisotopic Mass675.411134198
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C34H62NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,30-31H,3-4,9-29,35H2,1-2H3,(H,38,39)(H,40,41)/b7-5-,8-6-/t30-,31+/m1/s1
InChI KeyUJCPMSNQLZYMSK-XRLNPFBNSA-N