Showing metabocard for PS(14:1(9Z)/18:1(9Z)) (MMDBc0047252)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:16:19 UTC
Update Date2022-09-01 01:43:01 UTC
Metabolite IDMMDBc0047252
Metabolite Identification
Common NamePS(14:1(9Z)/18:1(9Z))
DescriptionPS(14:1(9Z)/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:1(9Z)/18:1(9Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of oleic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. 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, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. 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:0x00007f1241a37460>

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3D MOL for #<Metabolite:0x00007f1241a37460>

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3D SDF for #<Metabolite:0x00007f1241a37460>

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3D-SDF for #<Metabolite:0x00007f1241a37460>

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PDB for #<Metabolite:0x00007f1241a37460>

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3D PDB for #<Metabolite:0x00007f1241a37460>

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SMILES for #<Metabolite:0x00007f1241a37460>

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INCHI for #<Metabolite:0x00007f1241a37460>

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SynonymsNot Available
Molecular FormulaC38H70NO10P
Average Mass731.9369
Monoisotopic Mass731.473733977
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C38H70NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-37(41)49-34(32-47-50(44,45)48-33-35(39)38(42)43)31-46-36(40)29-27-25-23-21-19-14-12-10-8-6-4-2/h10,12,16-17,34-35H,3-9,11,13-15,18-33,39H2,1-2H3,(H,42,43)(H,44,45)/b12-10-,17-16-/t34-,35+/m1/s1
InChI KeyQBNCFMDNNPQYIL-NTEBNZJHSA-N