NP-MRD: Showing NP-Card for (2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid (NP0218193)

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Record Information

Version

1.0

Created at

2022-09-05 18:46:23 UTC

Updated at

2022-09-05 18:46:23 UTC

NP-MRD ID

NP0218193

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

Description

PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0), Also known as phosphatidylserine(22:6/18:0) Or PS(22:6/18:0), 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. Thus, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is considered to be a glycerophosphoserine lipid molecule. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Participates in a number of enzymatic reactions. In particular, choline and PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Can be biosynthesized from PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) And L-serine; which is mediated by the enzyme phosphatidylserine synthase. In addition, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Can be converted into PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0); Which is mediated by the enzyme phosphatidylserine decarboxylase. In humans, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is involved in phosphatidylethanolamine biosynthesis. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.E. (2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid is found in Aphis gossypii. It was first documented in 1995 (PMID: 7834746). The phosphate moiety, the amino group and the carboxyl function (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204042D          

 60 59  0  0  1  0            999 V2000
   23.9164   -6.2995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0175   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3424   -7.7616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6672   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6927   -7.7616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9921   -7.7616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8156   -8.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3677   -7.3719    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.9780   -6.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7576   -8.0470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0429   -6.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7180   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3931   -6.9821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.9302   -8.5710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.0892   -6.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8865   -6.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0892   -5.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8967   -7.6648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2749   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9894   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7039   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4184   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1329   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5618   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2763   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9908   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7052   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4197   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1342   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8487   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5632   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2776   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2776   -6.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3839   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0984   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8129   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5274   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2419   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9563   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6708   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3853   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0997   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8142   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5287   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2432   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9577   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6722   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1011   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1011   -9.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  6  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  3 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40  6  1  0  0  0  0
 40 41  2  0  0  0  0
 43 42  1  0  0  0  0
 44 43  1  0  0  0  0
 45 44  1  0  0  0  0
 46 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
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 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
 55 54  1  0  0  0  0
 56 55  1  0  0  0  0
 57 56  1  0  0  0  0
 58 57  1  0  0  0  0
 59 58  1  0  0  0  0
 60 59  2  0  0  0  0
  7 59  1  0  0  0  0
M  END


  Mrv0541 02241204042D          

 60 59  0  0  1  0            999 V2000
   23.9164   -6.2995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0175   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3424   -7.7616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6672   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6927   -7.7616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9921   -7.7616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8156   -8.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3677   -7.3719    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.9780   -6.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7576   -8.0470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0429   -6.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7180   -7.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3931   -6.9821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.9302   -8.5710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.0892   -6.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8865   -6.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0892   -5.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8967   -7.6648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2749   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9894   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7039   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4184   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1329   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5618   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2763   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9908   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7052   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4197   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1342   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8487   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5632   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2776   -7.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2776   -6.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3839   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0984   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8129   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5274   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2419   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9563   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6708   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3853   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0997   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8142   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5287   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2432   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9577   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6722   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -8.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1011   -8.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1011   -9.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  6  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  3 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
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 37 38  1  0  0  0  0
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 40  6  1  0  0  0  0
 40 41  2  0  0  0  0
 43 42  1  0  0  0  0
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 45 44  1  0  0  0  0
 46 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
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 55 54  1  0  0  0  0
 56 55  1  0  0  0  0
 57 56  1  0  0  0  0
 58 57  1  0  0  0  0
 59 58  1  0  0  0  0
 60 59  2  0  0  0  0
  7 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218193

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C46H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,18,20,23-24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,27-25-,33-31-/t42-,43+/m1/s1

> <INCHI_KEY>
YZPDRIODLGOXPQ-VQXQEPRVSA-N

> <FORMULA>
C46H78NO10P

> <MOLECULAR_WEIGHT>
836.086

> <EXACT_MASS>
835.536334233

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
96.28651821080179

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
10.878526145569046

> <ALOGPS_LOGS>
-7.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.1783960156533424

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991701996

> <JCHEM_PKA_STRONGEST_BASIC>
9.376604467850063

> <JCHEM_POLAR_SURFACE_AREA>
171.68

> <JCHEM_REFRACTIVITY>
240.34140000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.27e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  H   UNK     0      44.644 -11.759   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      39.233 -13.761   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.972 -14.488   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      36.712 -13.761   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      40.493 -14.488   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      35.452 -14.488   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      36.989 -15.944   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      41.753 -13.761   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      41.026 -12.501   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      42.481 -15.021   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      43.013 -13.033   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      44.274 -13.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.534 -13.033   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      39.070 -15.999   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      46.833 -11.889   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      48.321 -12.750   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      46.833 -10.312   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      46.474 -14.308   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.111 -14.488   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.444 -13.718   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.778 -14.488   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.112 -14.488   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.445 -13.718   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.779 -14.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.113 -14.488   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.446 -13.718   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.780 -14.488   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.114 -14.488   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.448 -13.718   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.781 -14.488   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.115 -14.488   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      23.449 -13.718   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.782 -14.488   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.116 -14.488   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.450 -13.718   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      28.783 -14.488   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.117 -14.488   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      31.451 -13.718   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      32.785 -14.488   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      34.118 -13.718   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      34.118 -12.178   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.983 -15.944   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.316 -16.714   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      15.650 -15.944   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.984 -16.714   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      18.317 -15.944   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.651 -16.714   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      20.985 -15.944   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.318 -16.714   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      23.652 -15.944   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      24.986 -16.714   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.319 -15.944   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      27.653 -16.714   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.987 -15.944   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.321 -16.714   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      31.654 -15.944   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      32.988 -16.714   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      34.322 -15.944   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      35.655 -16.714   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      35.655 -18.254   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    5                                                       
CONECT    3    2    4    7   14                                             
CONECT    4    3    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4   40                                                       
CONECT    7    3   59                                                       
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15   18    1                                             
CONECT   14    3                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39    6   41                                                  
CONECT   41   40                                                            
CONECT   42   43                                                            
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60    7                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  118    0
END

View in JSmol

Synonyms

Value	Source
1-Docosahexaenoyl-2-stearoyl-sn-glycero-3-phosphoserine	HMDB
Phosphatidylserine(22:6/18:0)	HMDB
Phosphatidylserine(22:6n3/18:0)	HMDB
Phosphatidylserine(22:6W3/18:0)	HMDB
Phosphatidylserine(40:6)	HMDB
PS(22:6/18:0)	HMDB
PS(22:6N3/18:0)	HMDB
PS(22:6W3/18:0)	HMDB
PS(40:6)	HMDB
pSer(22:6/18:0)	HMDB
pSer(22:6n3/18:0)	HMDB
pSer(22:6W3/18:0)	HMDB
pSer(40:6)	HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-octadecanoyl-sn-glycero-3-phosphoserine	HMDB
PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)	Lipid Annotator

Chemical Formula

C₄₆H₇₈NO₁₀P

Average Mass

836.0860 Da

Monoisotopic Mass

835.53633 Da

IUPAC Name

(2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O

InChI Identifier

InChI=1S/C46H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,18,20,23-24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,27-25-,33-31-/t42-,43+/m1/s1

InChI Key

YZPDRIODLGOXPQ-VQXQEPRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aphis gossypii	LOTUS Database	35616633

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

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010827 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.28	ALOGPS
logP	10.88	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	240.34 m³·mol⁻¹	ChemAxon
Polarizability	96.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012444

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029060

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52925937

PDB ID

Not Available

ChEBI ID

88445

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid (NP0218193)

MOL for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

3D MOL for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

3D SDF for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

3D-SDF for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

PDB for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

3D PDB for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

SMILES for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

INCHI for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

Structure for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)

3D Structure for NP0218193 ((2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid)