NP-MRD: Showing NP-Card for (2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0178778)

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Record Information

Version

2.0

Created at

2022-09-03 16:50:02 UTC

Updated at

2022-09-03 16:50:02 UTC

NP-MRD ID

NP0178778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Description

SM(d18:1/16:0), Also known as C16 sphingomyelin or N-PSPC, 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(D18:1/16:0) Is considered to be a phosphosphingolipid lipid molecule. (2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium is found in Trypanosoma brucei. (2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium was first documented in 1994 (PMID: 8106344). SM(d18:1/16:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 9034165).

Structure

MOL 3D MOL SDF PDB SMILES InChI

SM(d18:1/16:0)
  Mrv1652303062020222D          

 49 48  0  0  0  0            999 V2000
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    1.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0574    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2748    1.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0969    1.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5251    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9534    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6675    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3816    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0957    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8099    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5240    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2381    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9522    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6663    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3805    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0946    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8087    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0789   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7931   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5072   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2213   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  6  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9  6  1  0  0  0  0
  5  2  1  0  0  0  0
  1 16  1  0  0  0  0
  4 33  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  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 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
M  CHG  2   8  -1  12   1
M  END

     RDKit          3D

127126  0  0  0  0  0  0  0  0999 V2000
    1.7299   -1.6039   -6.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -0.5560   -6.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313   -0.8973   -4.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728    0.1749   -4.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092   -0.0902   -3.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290    0.9896   -3.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896    0.7821   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993    1.8792   -1.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216    3.2311   -1.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    3.5344   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7178    3.4261    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1186    2.1331    1.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3031    2.2656    2.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0933    2.5202    3.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    2.5808    3.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.8534    4.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0523    2.1695    5.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    2.1719    3.5911 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5706    2.3017    4.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022    3.6637    4.8721 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242    3.9762    6.1066 P   0  0  2  0  0  5  0  0  0  0  0  0
    4.1934    3.1930    5.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2007    3.4852    7.5716 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2113    5.6334    6.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389    5.9838    5.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042    7.4522    5.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    8.3316    5.0593 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.8975    9.4588    4.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    8.9508    6.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218    7.7342    4.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952    2.7432    2.4044 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    2.0113    1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    0.8976    1.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476    2.5706   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058    1.8110   -1.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.5605   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9848   -0.6426   -0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -1.8186   -1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -3.0824   -0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -3.5564   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591   -4.8398    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -5.9286   -0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283   -7.2624    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258   -7.9162    0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886   -8.2343   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9817   -7.1156   -1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389   -7.7015   -2.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0092   -8.4660   -2.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229   -1.6835   -5.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -1.2708   -7.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835   -2.5761   -6.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299   -0.5319   -7.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    0.4244   -5.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966   -1.8504   -5.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595   -0.9924   -4.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7657    1.1869   -4.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    0.1028   -5.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -0.1747   -2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5232   -1.0828   -3.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5065    1.9662   -3.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7259    1.0122   -4.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736   -0.1672   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    0.5721   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7120    1.6400   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564    1.8667   -2.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793    3.4514   -2.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1370    4.0172   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963    2.9993   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0546    4.6204   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771    3.9368    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6511    4.1150    0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695    1.4133    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0742    1.6971    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9586    3.1782    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302    1.4379    3.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695    2.6904    4.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070    2.4048    2.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5167    3.8935    4.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    2.7999    5.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    1.0882    3.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    1.9253    5.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4767    1.7017    4.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    5.6500    4.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0870    5.4371    5.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282    7.7554    6.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    7.5798    4.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   10.2239    4.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    9.0546    3.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    9.8830    4.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714   10.0283    6.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894    8.9141    7.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    8.4697    6.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657    7.2084    3.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411    7.1248    4.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    8.5826    3.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    3.6863    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666    3.0499    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184    3.5181   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068    1.7467   -1.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    2.5290   -2.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293    0.2726   -2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    0.7124   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406   -0.5877    0.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -0.9744   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -1.5060   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -2.0059   -2.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2984   -3.8342   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -2.9212    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -3.6931   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5259   -2.7690   -0.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2436   -4.6799    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -5.0175    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -5.8269   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -5.6163   -0.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872   -7.2616    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967   -7.9569   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3680   -7.4214    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160   -8.9210    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0399   -9.0499   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4314   -8.7455   -0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -6.4703   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534   -6.5919   -2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2167   -8.3717   -3.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468   -6.8330   -3.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -8.1450   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -8.2684   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -9.5409   -2.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  1
 21 22  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 18 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 18 80  1  6
 19 81  1  0
 19 82  1  0
 25 83  1  0
 25 84  1  0
 26 85  1  0
 26 86  1  0
 28 87  1  0
 28 88  1  0
 28 89  1  0
 29 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 34 97  1  0
 34 98  1  0
 35 99  1  0
 35100  1  0
 36101  1  0
 36102  1  0
 37103  1  0
 37104  1  0
 38105  1  0
 38106  1  0
 39107  1  0
 39108  1  0
 40109  1  0
 40110  1  0
 41111  1  0
 41112  1  0
 42113  1  0
 42114  1  0
 43115  1  0
 43116  1  0
 44117  1  0
 44118  1  0
 45119  1  0
 45120  1  0
 46121  1  0
 46122  1  0
 47123  1  0
 47124  1  0
 48125  1  0
 48126  1  0
 48127  1  0
 16 78  1  1
 17 79  1  0
 15 77  1  0
 14 76  1  0
 13 74  1  0
 13 75  1  0
 12 72  1  0
 12 73  1  0
 11 70  1  0
 11 71  1  0
 10 68  1  0
 10 69  1  0
  9 66  1  0
  9 67  1  0
  8 64  1  0
  8 65  1  0
  7 62  1  0
  7 63  1  0
  6 60  1  0
  6 61  1  0
  5 58  1  0
  5 59  1  0
  4 56  1  0
  4 57  1  0
  3 54  1  0
  3 55  1  0
  2 52  1  0
  2 53  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
M  CHG  2  23  -1  27   1
M  END

SM(d18:1/16:0)
  Mrv1652303062020222D          

 49 48  0  0  0  0            999 V2000
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    1.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0574    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2748    1.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0969    1.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5251    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9534    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6675    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3816    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0957    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8099    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5240    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2381    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9522    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6663    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3805    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0946    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8087    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0789   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7931   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5072   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2213   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  6  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9  6  1  0  0  0  0
  5  2  1  0  0  0  0
  1 16  1  0  0  0  0
  4 33  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  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 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
M  CHG  2   8  -1  12   1
M  END
> <DATABASE_ID>
NP0178778

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

> <INCHI_KEY>
RWKUXQNLWDTSLO-GWQJGLRPSA-N

> <FORMULA>
C39H79N2O6P

> <MOLECULAR_WEIGHT>
703.0281

> <EXACT_MASS>
702.567574782

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
88.7622979070575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.12

> <JCHEM_LOGP>
6.976057740861588

> <ALOGPS_LOGS>
-7.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.49920132064026

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.865155035270682

> <JCHEM_PKA_STRONGEST_BASIC>
-1.050204146041731

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
213.94190000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.27e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: SM(d18:1/16:0)                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM    4  N   UNK     0      -5.217  -0.663   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      -0.456   1.441   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      -1.226   2.775   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.545   2.211   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.879   1.441   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0       4.109   0.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.113   3.054   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.212   0.671   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.781   2.880   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.114   0.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.447   1.440   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.780   0.669   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.113   1.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.446   0.669   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.779   1.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.112   0.669   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.445   1.440   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.778   0.669   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.111   1.440   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -20.444   0.669   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.777   1.440   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.110   0.669   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.443   1.440   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.776   0.669   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.217  -1.433   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -11.883  -1.433   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.549  -1.433   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -22.547  -1.433   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -23.880  -0.662   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -25.213  -1.433   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -26.546  -0.662   0.000  0.00  0.00           C+0
CONECT    1    2    3    4   16                                             
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1   33                                                       
CONECT    5    6    2                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10    6                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    1   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   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                                                            
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   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                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4E)-2-(Palmitoylamino)-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
(2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
C16 Sphingomyelin	ChEBI
C16-Sphingomyelin	ChEBI
Hexadecanoyl sphingomyelin	ChEBI
N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-Hexadecanoylsphing-4-enine-1-phosphocholine	ChEBI
N-Hexadecanoylsphingomyelin	ChEBI
N-Palmitoyl-D-erythro-sphingosylphosphorylcholine	ChEBI
N-Palmitoylsphing-4-enine-1-phosphocholine	ChEBI
N-Palmitoylsphingomyelin	ChEBI
N-Palmitoylsphingosine-1-phosphocholine	ChEBI
Palmitoyl sphingomyelin	ChEBI
Palmitoyl sphingomyelin (D18:1/16:0)	ChEBI
Palmitoylsphingomyelin	ChEBI
SM(18:1/16:0)	ChEBI
Sphingomyelin (D18:1/16:0)	ChEBI
Sphingomyelin D18:1/16:0	ChEBI
Sphingomyelin(D18:1/16:0)	ChEBI
(2S,3R,4E)-2-(Palmitoylamino)-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
(2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
N-Palmitoylsphingosine-phosphorylcholine	HMDB
N-PSPC	HMDB
N-Palmitoyl-D-erythrosphingosylphosphorylcholine	HMDB
N-Palmitoyl-D-sphingomyelin	HMDB
N-Palmitoylsphingosylphosphorylcholine	HMDB
Sphingomyelin (D18:1 C16:0)	HMDB
Sphingomyelin (DC18:1/c16:0)	HMDB
Sphingomyelin 16:0	HMDB
Sphingomyelin	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphing-4-enine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-4-sphingenine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphingenine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-erythro-4-sphingenine	MetBuilder
SM(D18:1/16:0)	ChEBI

Chemical Formula

C₃₉H₇₉N₂O₆P

Average Mass

703.0281 Da

Monoisotopic Mass

702.56757 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

InChI Key

RWKUXQNLWDTSLO-GWQJGLRPSA-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
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:78646 )
sphingomyelin 34:1 (CHEBI:78646 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010003 )

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	5.12	ALOGPS
logP	6.98	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-1.1	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	36	ChemAxon
Refractivity	213.94 m³·mol⁻¹	ChemAxon
Polarizability	88.76 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

HMDB0010169

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027352

KNApSAcK ID

Not Available

Chemspider ID

8115562

KEGG Compound ID

Not Available

BioCyc ID

CPD66-42

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9939941

PDB ID

Not Available

ChEBI ID

78646

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 ]
LOTUS database [Link]

Showing NP-Card for (2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0178778)

MOL for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0178778 ((2-{[(2s,3r,4e)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)