NP-MRD: Showing NP-Card for SM(d18:1/22:0) (NP0091915)

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Record Information

Version

2.0

Created at

2022-05-11 18:51:55 UTC

Updated at

2022-05-11 18:51:55 UTC

NP-MRD ID

NP0091915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

SM(d18:1/22:0)

Description

SM(d18:1/22:0), Also known as C22 sphingomyelin, belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Thus, SM(D18:1/22:0) Is considered to be a phosphosphingolipid lipid molecule. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by SM(d18:1/22:0) Synthase. The plasma membrane of cells is highly enriched in SM(d18:1/22:0) And is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a SM(d18:1/22:0) Pool in the inner leaflet of the membrane. SM(d18:1/22:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. SM(d18:1/22:0) Can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme sphingomyelinase, which causes the accumulation of SM(d18:1/22:0) In spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. It usually consists of phosphorylcholine and ceramide. SM(d18:1/22:0) is found in Trypanosoma brucei. SM(d18:1/22:0) was first documented in 1994 (PMID: 8106344). SM(d18:1/22:0) Or SM(d18:1/22:0) Is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons (PMID: 9034165).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203392D          

 54 53  0  0  1  0            999 V2000
    4.2402   -4.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8156   -4.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3936   -3.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2445   -4.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2465   -2.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4102   -4.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5396   -3.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1113   -3.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9559   -4.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8226   -3.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6734   -4.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5402   -3.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3848   -4.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2514   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1024   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9691   -3.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8137   -4.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6799   -3.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3976   -3.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1089   -3.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8266   -3.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5312   -4.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5377   -3.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2554   -3.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2425   -4.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9665   -3.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9601   -4.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6842   -3.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6715   -4.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -3.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3890   -4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1172   -2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3995   -3.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5420   -3.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8243   -3.7746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1131   -3.3565    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1000   -5.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8176   -4.5991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8284   -3.4011    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.1196   -2.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0936   -5.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5637   -2.6610    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   20.3774   -4.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6882   -2.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2530   -3.7853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9707   -3.3785    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.5269   -4.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0980   -4.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3867   -4.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -4.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9578   -4.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288   -4.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -4.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1000   -4.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 39  1  0  0  0  0
  6 39  1  0  0  0  0
  7 39  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  1  0  0  0  0
 30 36  1  0  0  0  0
 31 37  1  0  0  0  0
 32 33  1  0  0  0  0
 32 39  1  0  0  0  0
 33 44  1  0  0  0  0
 34 35  1  0  0  0  0
 34 45  1  0  0  0  0
 35 36  1  0  0  0  0
 35 38  1  6  0  0  0
 36 40  1  1  0  0  0
 37 38  1  0  0  0  0
 37 41  2  0  0  0  0
 42 46  1  0  0  0  0
 43 46  2  0  0  0  0
 44 46  1  0  0  0  0
 45 46  1  0  0  0  0
 47  4  1  0  0  0  0
  2 47  1  0  0  0  0
 48  2  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
  1 51  1  0  0  0  0
 52  1  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
M  CHG  2  39   1  42  -1
M  END

     RDKit          3D

145144  0  0  0  0  0  0  0  0999 V2000
    2.7504   -6.2843   -1.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -7.7808   -2.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566   -8.2079   -3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -7.9722   -2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -8.6890   -1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043   -8.4245   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306   -6.9631   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5765   -6.4089    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -4.9558    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -4.6175    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5050   -5.3174    2.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854   -5.0482    3.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812   -5.3099    2.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4812   -4.5991    1.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869   -3.8004    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9553   -3.0896    0.3952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2914   -2.7165    0.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0540   -1.9419    0.1161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0950   -0.8681    1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970    0.0806    0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468    1.2628    2.1531 P   0  0  1  0  0  5  0  0  0  0  0  0
   -6.2714    1.0447    3.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    1.1119    3.1734 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.1937    2.7857    1.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321    3.3058    0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3907    4.6930    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    5.4472   -0.1531 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.4366    6.1175    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0610    6.5493   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    4.7730   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2652   -1.2728   -1.1475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199   -1.0790   -2.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -1.5474   -1.7179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2913   -0.4050   -3.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    0.0204   -3.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272    0.9835   -2.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    1.5531   -2.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7142    2.3608   -4.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    2.9552   -3.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    1.9473   -3.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986    2.7041   -3.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451    1.7731   -2.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    0.7332   -1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8880   -0.1693   -1.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0524    0.5421   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5122    1.1284    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.8212    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1423    3.0075    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1103    3.6134    1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7862    4.7996    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7540    5.4382    2.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4337    6.6040    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3978    7.2557    2.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1128    8.4154    1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -6.1067   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -5.7359   -2.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7990   -5.9336   -1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9938   -8.3861   -1.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359   -7.9116   -2.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381   -7.5881   -3.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6675   -9.2623   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317   -6.8717   -2.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -8.3480   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -9.7866   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8156   -8.3134   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138   -8.8353   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3757   -8.9412    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4499   -6.3456   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041   -6.8278    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115   -6.9925    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4816   -6.5712    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -4.5050    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236   -4.3848    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698   -4.9622    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606   -3.5099    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4688   -6.4537    2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229   -5.1034    3.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -5.7387    4.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   -4.0314    4.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636   -5.2141    3.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1232   -6.4364    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9785   -4.6534    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1387   -3.7323    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8646   -3.7862   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9894   -2.3392    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8382   -1.3424    2.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0875   -0.4249    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    3.3900    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    2.6569    0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7378    5.2282    1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    4.6210   -0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    5.4810    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571    6.5462    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088    7.0056    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    6.1476   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455    6.8360   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1967    7.4107   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    5.5720   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308    4.1103   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2423   -0.9379   -1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 56  1  0
  1 57  1  0
M  CHG  2  23  -1  27   1
M  END


  Mrv0541 02241203392D          

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  2 47  1  0  0  0  0
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  1 51  1  0  0  0  0
 52  1  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
M  CHG  2  39   1  42  -1
M  END
> <DATABASE_ID>
NP0091915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C45H91N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h36,38,43-44,48H,6-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b38-36+/t43-,44+/m0/s1

> <INCHI_KEY>
FJJANLYCZUNFSE-TWKUQIQBSA-N

> <FORMULA>
C45H91N2O6P

> <MOLECULAR_WEIGHT>
787.1876

> <EXACT_MASS>
786.661475166

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
101.39088345304572

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4E)-2-docosanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
10.732813826195079

> <ALOGPS_LOGS>
-7.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.499201320641198

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8709150288593719

> <JCHEM_PKA_STRONGEST_BASIC>
0.011796153944246268

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
241.54790000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
C22 sphingomyelin

> <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  C   UNK     0       7.915  -9.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.589  -8.445   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.935  -6.878   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.256  -8.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.393  -5.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.832  -7.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.941  -7.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.274  -6.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.584  -9.245   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.602  -6.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.924  -8.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.942  -6.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.252  -9.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.269  -6.920   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.591  -8.505   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.609  -6.161   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.919  -9.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.936  -6.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.276  -6.181   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.603  -6.962   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.943  -6.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.258  -8.525   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.270  -6.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.610  -6.223   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.586  -9.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.937  -7.004   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.926  -8.545   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.277  -6.244   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.253  -9.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.605  -7.025   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.593  -8.565   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      41.285  -5.568   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      39.946  -6.328   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.612  -6.286   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.272  -7.046   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.944  -6.265   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      31.920  -9.345   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      33.260  -8.585   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      42.613  -6.349   0.000  0.00  0.00           N+1
HETATM   40  O   UNK     0      31.957  -4.725   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      31.908 -10.885   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      36.519  -4.967   0.000  0.00  0.00           O-1
HETATM   43  O   UNK     0      38.038  -7.646   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      38.618  -5.547   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      35.939  -7.066   0.000  0.00  0.00           O+0
HETATM   46  P   UNK     0      37.279  -6.307   0.000  0.00  0.00           P+0
HETATM   47  C   UNK     0      15.917  -9.225   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.250  -9.205   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.922  -8.425   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.582  -9.185   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.255  -8.405   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.587  -8.385   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.248  -9.145   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.920  -8.365   0.000  0.00  0.00           C+0
CONECT    1   51   52                                                       
CONECT    2   47   48                                                       
CONECT    3    8                                                            
CONECT    4    9   47                                                       
CONECT    5   39                                                            
CONECT    6   39                                                            
CONECT    7   39                                                            
CONECT    8    3   10                                                       
CONECT    9    4   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   22                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   23                                                       
CONECT   22   17   25                                                       
CONECT   23   21   24                                                       
CONECT   24   23   26                                                       
CONECT   25   22   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   36                                                       
CONECT   31   29   37                                                       
CONECT   32   33   39                                                       
CONECT   33   32   44                                                       
CONECT   34   35   45                                                       
CONECT   35   34   36   38                                                  
CONECT   36   30   35   40                                                  
CONECT   37   31   38   41                                                  
CONECT   38   35   37                                                       
CONECT   39    5    6    7   32                                             
CONECT   40   36                                                            
CONECT   41   37                                                            
CONECT   42   46                                                            
CONECT   43   46                                                            
CONECT   44   33   46                                                       
CONECT   45   34   46                                                       
CONECT   46   42   43   44   45                                             
CONECT   47    4    2                                                       
CONECT   48    2   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50    1                                                       
CONECT   52    1   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  106    0
END

View in JSmol

Synonyms

Value	Source
Behenoyl sphingomyelin	ChEBI
Behenoyl sphingomyelin (D18:1/22:0)	ChEBI
C22 Sphingomyelin	ChEBI
N-(Docosanoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-(Docosanoyl)-sphingosine-1-phosphocholine	ChEBI
Sphingomyelin (D18:1/22:0)	ChEBI
Sphingomyelin	HMDB
N-(Docosanoyl)-1-phosphocholine-sphing-4-enine	HMDB
Sphingomyelin(D18:1/22:0)	HMDB
N-(Docosanoyl)-1-phosphocholine-sphingosine	HMDB
N-(Docosanoyl)-1-phosphocholine-D-erythro-sphingosine	HMDB
N-(Docosanoyl)-1-phosphocholine-4-sphingenine	HMDB
N-(Docosanoyl)-1-phosphocholine-D-sphingosine	HMDB
N-(Docosanoyl)-1-phosphocholine-sphingenine	HMDB
N-(Docosanoyl)-1-phosphocholine-erythro-4-sphingenine	HMDB
Behenoylsphingomyelin	HMDB
C22-Sphingomyelin	HMDB
N-Behenoyl-D-erythro-sphingosylphosphorylcholine	HMDB
N-Behenoylsphingosine-1-phosphocholine	HMDB
Sphingomyelin (D18:1 C22:0)	HMDB
Sphingomyelin 22:0	HMDB

Chemical Formula

C₄₅H₉₁N₂O₆P

Average Mass

787.1876 Da

Monoisotopic Mass

786.66148 Da

IUPAC Name

(2-{[(2S,3R,4E)-2-docosanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

C22 sphingomyelin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C45H91N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h36,38,43-44,48H,6-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b38-36+/t43-,44+/m0/s1

InChI Key

FJJANLYCZUNFSE-TWKUQIQBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic zwitterion
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sphingomyelin d18:1 (CHEBI:74532 )
sphingomyelin 40:1 (CHEBI:74532 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010006 )

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	6.05	ALOGPS
logP	10.73	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.012	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	241.55 m³·mol⁻¹	ChemAxon
Polarizability	101.39 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

HMDB0012103

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028768

KNApSAcK ID

Not Available

Chemspider ID

24846873

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44260125

PDB ID

Not Available

ChEBI ID

74532

Good Scents ID

Not Available

References

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. [PubMed:8106344 ]

Showing NP-Card for SM(d18:1/22:0) (NP0091915)

MOL for NP0091915 (SM(d18:1/22:0))

3D MOL for NP0091915 (SM(d18:1/22:0))

3D SDF for NP0091915 (SM(d18:1/22:0))

3D-SDF for NP0091915 (SM(d18:1/22:0))

PDB for NP0091915 (SM(d18:1/22:0))

3D PDB for NP0091915 (SM(d18:1/22:0))

SMILES for NP0091915 (SM(d18:1/22:0))

INCHI for NP0091915 (SM(d18:1/22:0))

Structure for NP0091915 (SM(d18:1/22:0))

3D Structure for NP0091915 (SM(d18:1/22:0))