NP-MRD: Showing NP-Card for SM(d18:0/12:0) (NP0091899)

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Record Information

Version

2.0

Created at

2022-05-11 18:51:27 UTC

Updated at

2022-05-11 18:51:27 UTC

NP-MRD ID

NP0091899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

SM(d18:0/12:0)

Description

SM(d18:0/12:0), Also known as 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. SM(d18:0/12:0) Is a very strong basic compound (based on its pKa). SM(d18:0/12:0) (D18:0/12:0) Or SM(d18:0/12:0) Is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. However, there is some evidence that there may also be a SM(d18:0/12:0) Pool in the inner leaflet of the membrane. In humans, SM(d18:0/12:0) Is the only membrane phospholipid not derived from glycerol. In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. SMs play a role in signal transduction. SM(d18:0/12:0) Can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. SM(d18:0/12:0) was first documented in 1997 (PMID: 9034165). Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of SM(d18:0/12:0) In spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203382D          

 44 43  0  0  1  0            999 V2000
   21.2444   -3.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3724   -3.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -5.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2230   -3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -4.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5378   -4.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6506   -2.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8158   -4.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9438   -3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1091   -4.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2219   -2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3872   -4.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5152   -3.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6804   -4.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7933   -2.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9590   -4.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2521   -4.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5303   -4.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8235   -4.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0865   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1016   -4.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3949   -4.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3647   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6731   -4.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6579   -3.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9663   -4.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9361   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2445   -4.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2293   -3.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -5.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2522   -4.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1091   -4.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8158   -4.1888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5376   -4.5883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5077   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8011   -3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235   -4.6928    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.5528   -5.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4926   -2.1142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1062   -5.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -3.9341    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.9740   -5.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3875   -4.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -4.6408    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3 37  1  0  0  0  0
  4 37  1  0  0  0  0
  5 37  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  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 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  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 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 31  1  0  0  0  0
 30 37  1  0  0  0  0
 31 42  1  0  0  0  0
 33 32  1  6  0  0  0
 32 43  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  0  0  0  0
 34 38  1  1  0  0  0
 35 36  1  0  0  0  0
 35 39  1  0  0  0  0
 40 44  2  0  0  0  0
 41 44  1  0  0  0  0
 42 44  1  0  0  0  0
 43 44  1  0  0  0  0
M  CHG  2  37   1  41  -1
M  END

     RDKit          3D

119118  0  0  0  0  0  0  0  0999 V2000
    2.2108   -0.2065   -5.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1083    0.2404   -4.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988    1.4762   -4.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783    2.7901   -5.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3766    3.2543   -6.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535    2.7042   -6.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1248    2.7112   -5.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    2.1561   -5.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3479    1.9999   -4.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.2262   -3.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836    1.5055   -2.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    1.5967   -1.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    1.7788   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    0.6244    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    0.9111    1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -0.2388    2.6961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1325    0.1268    3.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -0.7776    2.6635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8790    0.2608    3.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108    1.4336    2.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655    2.5357    3.1218 P   0  0  2  0  0  5  0  0  0  0  0  0
   -3.8704    2.3926    4.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4962    2.0661    2.5849 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5490    4.0880    2.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2750    4.1248    2.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882    5.4736    1.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    6.0876    0.7155 N   0  0  1  0  0  4  0  0  0  0  0  0
   -3.6344    5.2664    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212    7.3311    1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    6.4551   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943   -1.9083    3.4544 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4759   -3.1267    3.4414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2711   -4.0327    4.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1003   -3.2517    4.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4219   -4.6883    3.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7641   -4.7062    4.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668   -6.0522    4.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427   -6.3334    2.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -5.2716    2.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -5.4631    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416   -5.4290    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113   -5.5826   -1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9134   -4.4793   -1.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -3.1104   -1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358   -0.0804   -5.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    0.2450   -6.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516   -1.3186   -5.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816    0.2862   -3.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.6040   -4.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6188    1.4928   -4.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6835    1.3024   -5.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495    3.0242   -3.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    3.5686   -5.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999    4.4081   -6.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514    3.1704   -7.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063    3.5472   -6.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938    1.8503   -6.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    3.7280   -4.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347    1.9456   -4.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947    1.1579   -6.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4670    2.7822   -6.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656    1.6540   -5.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8098    3.0614   -4.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    0.0804   -3.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7084    1.2081   -3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903    2.4944   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511    0.7960   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2252    2.6261   -2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305    0.7815   -2.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    1.9398   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917    2.7489   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239    0.3202    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143   -0.2600   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9366    1.0127    1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    1.8309    2.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639   -1.0290    2.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6173   -0.3541    4.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585   -0.9797    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7503    0.3674    4.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181   -0.1569    3.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    3.7998    3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697    3.3746    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592    5.3059    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520    6.1028    2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0196    5.7712   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070    4.2670   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039    5.2633    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4960    7.9832    0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8752    7.0277    1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    7.8395    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274    5.4864   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3976    6.8545   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436    7.1522   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9597   -1.8692    4.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -3.6665    2.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766   -4.2274    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -2.5508    3.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154   -3.0993    5.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332   -5.4129    4.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538   -4.9608    2.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -4.6221    5.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200   -3.8720    4.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -5.9480    4.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -6.8380    4.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -7.3234    2.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -6.4149    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435   -5.1057    3.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -4.2901    2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186   -6.4412    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -4.6336    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2592   -4.4419    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553   -6.2438    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -5.4225   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -6.5492   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -4.5916   -3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813   -4.5245   -1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2395   -2.8530   -0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -2.3687   -2.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -2.9646   -2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  6
 21 22  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 27 26  1  1
 27 28  1  0
 27 29  1  0
 27 30  1  0
 18 31  1  0
 31 32  1  0
 32 33  1  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
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  0
 11 67  1  0
 12 68  1  0
 12 69  1  0
 13 70  1  0
 13 71  1  0
 14 72  1  0
 14 73  1  0
 15 74  1  0
 15 75  1  0
 16 76  1  6
 17 77  1  0
 18 78  1  6
 19 79  1  0
 19 80  1  0
 25 81  1  0
 25 82  1  0
 26 83  1  0
 26 84  1  0
 28 85  1  0
 28 86  1  0
 28 87  1  0
 29 88  1  0
 29 89  1  0
 29 90  1  0
 30 91  1  0
 30 92  1  0
 30 93  1  0
 31 94  1  0
 32 95  1  6
 33 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
 44119  1  0
M  CHG  2  23  -1  27   1
M  END


  Mrv0541 02241203382D          

 44 43  0  0  1  0            999 V2000
   21.2444   -3.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3724   -3.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -5.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2230   -3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -4.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5378   -4.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6506   -2.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8158   -4.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9438   -3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1091   -4.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2219   -2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3872   -4.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5152   -3.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6804   -4.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7933   -2.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9590   -4.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2521   -4.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5303   -4.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8235   -4.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0865   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1016   -4.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3949   -4.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3647   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6731   -4.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6579   -3.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9663   -4.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9361   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2445   -4.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2293   -3.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -5.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2522   -4.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1091   -4.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8158   -4.1888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5376   -4.5883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5077   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8011   -3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235   -4.6928    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.5528   -5.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4926   -2.1142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1062   -5.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -3.9341    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.9740   -5.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3875   -4.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -4.6408    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3 37  1  0  0  0  0
  4 37  1  0  0  0  0
  5 37  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  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 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  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 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 31  1  0  0  0  0
 30 37  1  0  0  0  0
 31 42  1  0  0  0  0
 33 32  1  6  0  0  0
 32 43  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  0  0  0  0
 34 38  1  1  0  0  0
 35 36  1  0  0  0  0
 35 39  1  0  0  0  0
 40 44  2  0  0  0  0
 41 44  1  0  0  0  0
 42 44  1  0  0  0  0
 43 44  1  0  0  0  0
M  CHG  2  37   1  41  -1
M  END
> <DATABASE_ID>
NP0091899

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C35H75N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h33-36,38-39H,6-32H2,1-5H3/t33-,34+,35?/m0/s1

> <INCHI_KEY>
DBRCJAPVYYEHRO-GWDKEWMYSA-N

> <FORMULA>
C35H75N2O6P

> <MOLECULAR_WEIGHT>
650.9536

> <EXACT_MASS>
650.536274654

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
82.77632340833456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
4.443285584687664

> <ALOGPS_LOGS>
-7.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.80961583032824

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8172627300642468

> <JCHEM_PKA_STRONGEST_BASIC>
9.081928273739791

> <JCHEM_POLAR_SURFACE_AREA>
111.08000000000001

> <JCHEM_REFRACTIVITY>
195.6921

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.35e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

> <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      39.656  -7.430   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.295  -5.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.258 -10.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.750  -7.412   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.656  -8.014   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.337  -8.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.948  -5.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.990  -7.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.628  -6.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.670  -8.273   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.281  -5.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.323  -7.527   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.962  -6.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.003  -8.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.614  -5.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.657  -7.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.337  -8.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.990  -7.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.671  -8.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.295  -6.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.323  -7.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.004  -8.468   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.947  -5.388   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.657  -7.722   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.628  -6.182   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.337  -8.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.281  -5.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.990  -7.771   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.961  -6.231   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.351  -9.505   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.671  -8.711   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.004  -8.613   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.323  -7.819   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.670  -8.565   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.614  -5.486   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      18.295  -6.280   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       9.004  -8.760   0.000  0.00  0.00           N+1
HETATM   38  O   UNK     0      19.699 -10.105   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      19.586  -3.947   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      15.132  -9.982   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      13.543  -7.344   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0      13.018  -9.457   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      15.657  -7.869   0.000  0.00  0.00           O+0
HETATM   44  P   UNK     0      14.338  -8.663   0.000  0.00  0.00           P+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   37                                                            
CONECT    4   37                                                            
CONECT    5   37                                                            
CONECT    6    1    8                                                       
CONECT    7    2    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   20                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   21                                                       
CONECT   20   15   23                                                       
CONECT   21   19   22                                                       
CONECT   22   21   24                                                       
CONECT   23   20   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   34                                                       
CONECT   29   27   35                                                       
CONECT   30   31   37                                                       
CONECT   31   30   42                                                       
CONECT   32   33   43                                                       
CONECT   33   32   34   36                                                  
CONECT   34   28   33   38                                                  
CONECT   35   29   36   39                                                  
CONECT   36   33   35                                                       
CONECT   37    3    4    5   30                                             
CONECT   38   34                                                            
CONECT   39   35                                                            
CONECT   40   44                                                            
CONECT   41   44                                                            
CONECT   42   31   44                                                       
CONECT   43   32   44                                                       
CONECT   44   40   41   42   43                                             
MASTER        0    0    0    0    0    0    0    0   44    0   86    0
END

View in JSmol

Synonyms

Value	Source
C12 Sphingomyelin	HMDB
N-(Dodecanoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	HMDB
Sphingomyelin (D18:0/12:0)	HMDB
N-(Dodecanoyl)-1-phosphocholine-sphinganine	HMDB
Sphingomyelin(D18:0/12:0)	HMDB
N-(Dodecanoyl)-1-phosphocholine-dihydrosphingosine	HMDB
N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphinganine	HMDB

Chemical Formula

C₃₅H₇₅N₂O₆P

Average Mass

650.9536 Da

Monoisotopic Mass

650.53627 Da

IUPAC Name

(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-3-hydroxy-2-[(1-hydroxydodecyl)amino]octadecyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C35H75N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h33-36,38-39H,6-32H2,1-5H3/t33-,34+,35?/m0/s1

InChI Key

DBRCJAPVYYEHRO-GWDKEWMYSA-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

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
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Hemiaminal
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Alkanolamine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Organic salt
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	3.76	ALOGPS
logP	4.44	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.08 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	195.69 m³·mol⁻¹	ChemAxon
Polarizability	82.78 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

HMDB0012084

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028752

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481358

PDB ID

Not Available

ChEBI ID

Not Available

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 ]

Showing NP-Card for SM(d18:0/12:0) (NP0091899)

MOL for NP0091899 (SM(d18:0/12:0))

3D MOL for NP0091899 (SM(d18:0/12:0))

3D SDF for NP0091899 (SM(d18:0/12:0))

3D-SDF for NP0091899 (SM(d18:0/12:0))

PDB for NP0091899 (SM(d18:0/12:0))

3D PDB for NP0091899 (SM(d18:0/12:0))

SMILES for NP0091899 (SM(d18:0/12:0))

INCHI for NP0091899 (SM(d18:0/12:0))

Structure for NP0091899 (SM(d18:0/12:0))

3D Structure for NP0091899 (SM(d18:0/12:0))