Phosphatidylserine
PubChem CID: 9547096
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| Compound Synonyms | Distearoylphosphatidylserine, Phosphatidylserine, 51446-62-9, Phosphotidylserine, 1,2-dioctadecanoyl-sn-glycero-3-phosphoserine, Distearoyl phosphatidylserine, PS(18:0/18:0), Phosphatidyl serine [WHO-DD], 394XK0IH40, (2S)-2-Amino-3-((((R)-2,3-bis(stearoyloxy)propoxy)-(hydroxy)phosphoryl)oxy)propanoic acid, Phosphatidylserine [INCI], Phosphatidylserine(36:0), Dioctadecanoylphosphatidylserine, PSer(36:0), 1446756-47-3, PHOSPHATIDYLSERINE [VANDF], PHOSPHOTIDYLSERINE [VANDF], Phosphatidylserine(18:0/18:0), PSer(18:0/18:0), (2S)-2-amino-3-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxypropanoic acid, 1,2-distearoyl-sn-glycero-3-phosphoserine, Phosphatidylserines (bovine), 1,2-distearoyl-sn-glycero-3-phospho-l-serine, L-Serine, 2,3-bis[(1-oxooctadecyl)oxy]propyl ester, dihydrogen phosphate (ester), (R)-, O-[(R)-{[(2r)-2,3-Bis(Octadecanoyloxy)propyl]oxy}(Hydroxy)phosphoryl]-L-Serine, PS(36:0), Phosphatidyl Serines, Serine, Phosphatidyl, Serines, Phosphatidyl, Serine Phosphoglycerides, Phosphoglycerides, Serine, (2S)-2-amino-3-(((2R)-2,3-di(octadecanoyloxy)propoxy)-hydroxyphosphoryl)oxypropanoic acid, (2S)-2-azaniumyl-3-(((2R)-2,3-di(octadecanoyloxy)propoxy)-hydroxyphosphoryl)oxypropanoate, (2S)-2-azaniumyl-3-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxypropanoate, Phospholipid Serine, (2S)-2-amino-3-((((2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy)(hydroxy)phosphoryl)oxy)propanoic acid, (2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid, L-1-phosphatidylserine, L-a-Phosphatidyl-L-serine, SCHEMBL24649, UNII-394XK0IH40, CHEMBL4297669, CHEBI:84519, DTXSID10866199, DTXSID401058684, LMGP03010036, MFCD00135635, AKOS016011101, FP16194, FP47183, DA-76830, DA-76831, 1,2-distearoyl-rac-glycero-3-phosphoserine, PS(36:00), H12024, 1,2-Diacyl-sn-glycero-3-phospho-L-serine, Ptd-L-Ser, Q27157825, O-{[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}-L-serine, (2S)-2-Amino-3-((((R)-2,3-bis(stearoyloxy)propoxy)-(hydroxy)phosphoryl)oxy)propanoicacid, (2S,8R)-2-Amino-5-hydroxy-11-oxo-8-[(1-oxooctadecyl)oxy]-4,6,10-trioxa-5-phosphaoctacosanoic acid 5-oxide sodium salt, 1,2-Diacyl-sn-glycero-3-phospho-L-serine, Phosphatidylethanolamine, L-a-Cephalin, 3-sn-Phosphatidylethanolamine |
|---|---|
| Topological Polar Surface Area | 172.0 |
| Hydrogen Bond Donor Count | 3.0 |
| Heavy Atom Count | 54.0 |
| Description | PS(18:0/18:0) 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(18:0/18:0), in particular, consists of two octadecanoyl 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. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 937.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 2.0 |
| Enzyme Uniprot Id | P48651, Q8WTV0, Q9UG56, Q9BVG9, Q3SYC2, O15357, Q53H76, Q969G5, Q08431 |
| Uniprot Id | O15496, P49619, P23743, Q16760, Q9Y6T7, P17252, Q9Y2Q0, O15162, P48651, Q8WTV0, Q9H2A7, Q9UG56, Q6NYC1, Q9BVG9, Q3SYC2, O00443, O15357, Q8N3E9, Q9NY59, Q9NRY7, Q9NRY6, Q9NRQ2, A0PG75, Q53H76, O95810, P46100, Q99829, O95741, Q15642, Q5T0N5, Q96RU3, Q9NXE4, Q9NRX5, Q969G5, O76027, B2WTI4, Q86VE9, Q9Y6U3, A6NH21, B2WTI3, Q08431 |
| Iupac Name | (2S)-2-amino-3-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxypropanoic acid |
| Prediction Hob | 0.0 |
| Class | Glycerophospholipids |
| Xlogp | 12.1 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Glycerophosphoserines |
| Molecular Formula | C42H82NO10P |
| Prediction Swissadme | 0.0 |
| Inchi Key | TZCPCKNHXULUIY-RGULYWFUSA-N |
| Fcsp3 | 0.9285714285714286 |
| Logs | -2.378 |
| Rotatable Bond Count | 44.0 |
| State | Solid |
| Logd | 3.849 |
| Synonyms | 1,2-Distearoyl-rac-glycero-3-oserine, 1,2-distearoyl-rac-glycero-3-phosphoserine, Atidylserine(18:0/18:0), Atidylserine(36:0), Phosphatidylserine(18:0/18:0), Phosphatidylserine(36:0), PS(18:0/18:0), PS(36:0), PSer(18:0/18:0), PSer(36:0), 1,2-Dioctadecanoyl-sn-glycero-3-phosphoserine, Distearoyl phosphatidylserine, pSer(18:0/18:0), pSer(36:0), 1,2-Distearoyl-rac-glycero-3-phosphoserine, 1,2-Dioctadecanoyl-rac-glycero-3-phosphoserine |
| Compound Name | Phosphatidylserine |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 791.568 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 791.568 |
| Hydrogen Bond Acceptor Count | 11.0 |
| Molecular Weight | 792.1 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 2.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Esol | -9.444751799999995 |
| Inchi | InChI=1S/C42H82NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h38-39H,3-37,43H2,1-2H3,(H,46,47)(H,48,49)/t38-,39+/m1/s1 |
| Smiles | CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N)OC(=O)CCCCCCCCCCCCCCCCC |
| Nring | 0.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Phosphatidylserines |
- 1. Outgoing r'ship
FOUND_INto/from Vitis Vinifera (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all