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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (52) Show 52 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-03-24 16:57:21 UTC

Update Date

2023-07-07 20:54:00 UTC

HMDB ID

HMDB0013463

Secondary Accession Numbers

HMDB13463

Metabolite Identification

Common Name

Hydroxysphingomyeline C16:1

Description

Sphingomyelin (d18:0/16:1(9Z)(OH)) or SM(d18:0/16:1(9Z)(OH)) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin 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 sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin 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 Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652302132020362D          

 49 48  0  0  1  0            999 V2000
    4.0976   -3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9507   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1143   -3.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2438   -3.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -2.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5266   -3.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2442   -2.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9554   -3.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3839   -3.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1016   -2.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8129   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5306   -2.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2417   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9594   -2.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6706   -3.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3883   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0996   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8212   -2.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1036   -3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2461   -3.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5284   -3.4367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8171   -3.0186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5217   -4.2612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5325   -3.0633    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   14.8236   -2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2678   -2.3230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.0816   -3.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3923   -2.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9570   -3.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6747   -3.0407    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.5191   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2335   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9480   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6625   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3770   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8059   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5204   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2349   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9493   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6638   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3783   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0928   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8073   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8073   -5.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3783   -5.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 20 29  1  0  0  0  0
 21 22  1  0  0  0  0
 21 30  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 23 26  1  1  0  0  0
 27 31  1  0  0  0  0
 28 31  2  0  0  0  0
 29 31  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 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 24  1  0  0  0  0
 45 46  2  0  0  0  0
 47 43  1  0  0  0  0
 48 32  1  0  0  0  0
 49 48  1  0  0  0  0
M  CHG  2  25   1  27  -1
M  END

HMDB0013463
     RDKit          3D
SM(d18:0/16:1(9Z)(OH))
126125  0  0  0  0  0  0  0  0999 V2000
  -11.6069   -4.8668   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5159   -4.6295    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9685   -4.7729    1.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0357   -3.9784    2.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7186   -3.4964    1.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5870   -2.2858    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1574   -2.1554   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4675   -2.0025   -1.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9961   -1.9424   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5251   -0.6339   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0256   -0.5945   -1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716   -0.6574   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.5866   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -0.6183    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -1.7900    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.5297    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3628    0.7222   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    1.5520   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    1.0016   -0.0648 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    2.2223   -0.6592 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0702    3.0803    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    3.3607    1.3865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309    4.2966    2.6746 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7617    3.4721    3.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    4.4804    3.8573 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3048    5.7463    2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    6.5630    1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    7.8191    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    8.7612    0.4146 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0053    8.1865   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   10.0436    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757    8.8697    1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    1.8393   -1.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3569    0.9471   -2.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    1.3439   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971    0.0666   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.4644    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    0.5397    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765    1.2724   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9468    0.3173   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373   -0.3150    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.2301   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0940   -2.3304   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0696   -3.2345   -1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0360   -3.8319   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3188   -4.6217    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3199   -5.1870    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2903   -6.0931    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5691   -7.2458   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5291   -4.9211   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7221   -4.0593   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8981   -5.8052   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0549   -3.6507    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3686   -5.3846    0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9165   -4.8674    2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6619   -5.9142    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6509   -3.0856    2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770   -4.5665    3.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1152   -3.2525    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0509   -4.3375    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0802   -1.3900    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5104   -1.8909    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2684   -2.1380   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9886   -1.9099   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6070   -2.7439   -2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4772   -2.1304   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8753    0.2088   -1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9266   -0.4746   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113   -1.4312   -2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7542    0.3688   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.2440   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121   -1.5336   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7542    0.3107   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -1.5185   -1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.2642    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683   -1.5598    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -1.4278    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.5248    1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    0.3419    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1745    2.7610   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817    2.5588    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    4.0391    0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    5.9905    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    6.7869    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    8.3343    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    7.5998    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    7.4108   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    7.7094   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1273    8.9756   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    9.9650   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598   10.7971   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   10.3819    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698    7.9701    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    8.7999    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    9.8081    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    2.7530   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.4175   -2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4332    2.0917   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4462   -0.6555   -1.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7312   -1.0874    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129   -1.1653   -0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345    0.1377    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307    1.3100    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4940    1.8202   -0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163    2.0200    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3122   -0.3358   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551    0.9405   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023    0.5144    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2650   -0.8687    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3721   -0.5871   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
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 47121  1  0
 48122  1  0
 48123  1  0
 49124  1  0
 49125  1  0
 49126  1  0
M  CHG  2  25  -1  29   1
M  END


  Mrv1652302132020362D          

 49 48  0  0  1  0            999 V2000
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    6.9554   -3.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6706   -3.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3883   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1036   -3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2461   -3.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5284   -3.4367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8171   -3.0186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   20.5325   -3.0633    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   14.8236   -2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5191   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8073   -5.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3783   -5.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046   -4.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -4.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 18 23  1  0  0  0  0
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 23 26  1  1  0  0  0
 27 31  1  0  0  0  0
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 45 24  1  0  0  0  0
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 47 43  1  0  0  0  0
 48 32  1  0  0  0  0
 49 48  1  0  0  0  0
M  CHG  2  25   1  27  -1
M  END
> <DATABASE_ID>
HMDB0013463

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1

> <INCHI_KEY>
LPHMSPONPQCKTL-FKUNDBCPSA-N

> <FORMULA>
C39H77N2O7P

> <MOLECULAR_WEIGHT>
717.0116

> <EXACT_MASS>
716.54683934

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
87.13220176091059

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
5.383325017194925

> <ALOGPS_LOGS>
-7.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.386107316070731

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.864788889978064

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5374968164983756

> <JCHEM_POLAR_SURFACE_AREA>
128.14999999999998

> <JCHEM_REFRACTIVITY>
216.57400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
35

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013463
     RDKit          3D
SM(d18:0/16:1(9Z)(OH))
126125  0  0  0  0  0  0  0  0999 V2000
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   -9.5870   -2.2858    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1574   -2.1554   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4675   -2.0025   -1.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9961   -1.9424   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5251   -0.6339   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0256   -0.5945   -1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716   -0.6574   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.5866   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -0.6183    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -1.7900    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.5297    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3628    0.7222   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    1.5520   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    1.0016   -0.0648 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    2.2223   -0.6592 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0702    3.0803    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    3.3607    1.3865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309    4.2966    2.6746 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7617    3.4721    3.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    4.4804    3.8573 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3048    5.7463    2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    6.5630    1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    7.8191    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    8.7612    0.4146 N   0  0  0  0  0  4  0  0  0  0  0  0
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   -0.9757    8.8697    1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    1.8393   -1.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3569    0.9471   -2.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0971    0.0666   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.4644    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    0.5397    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765    1.2724   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9468    0.3173   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373   -0.3150    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.2301   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0696   -3.2345   -1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0360   -3.8319   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3188   -4.6217    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3199   -5.1870    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2903   -6.0931    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5691   -7.2458   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6619   -5.9142    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6509   -3.0856    2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770   -4.5665    3.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1152   -3.2525    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0509   -4.3375    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0802   -1.3900    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5104   -1.8909    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2684   -2.1380   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9886   -1.9099   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6070   -2.7439   -2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4772   -2.1304   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8753    0.2088   -1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9266   -0.4746   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113   -1.4312   -2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7542    0.3688   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.2440   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121   -1.5336   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7542    0.3107   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -1.5185   -1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.2642    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683   -1.5598    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -1.4278    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.5248    1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    0.3419    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1745    2.7610   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817    2.5588    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    4.0391    0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    5.9905    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    6.7869    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    8.3343    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    7.5998    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    7.4108   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    7.7094   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1273    8.9756   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    9.9650   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598   10.7971   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   10.3819    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698    7.9701    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    8.7999    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    9.8081    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    2.7530   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.4175   -2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4332    2.0917   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4462   -0.6555   -1.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7312   -1.0874    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129   -1.1653   -0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345    0.1377    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307    1.3100    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4940    1.8202   -0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163    2.0200    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3122   -0.3358   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551    0.9405   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023    0.5144    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2650   -0.8687    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3721   -0.5871   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5319   -1.6034    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4483   -2.8450   -0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774   -1.9249   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5447   -4.0109   -2.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6550   -2.6214   -2.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6345   -3.0199   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7699   -4.4901   -1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5967   -3.9901    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7453   -5.4449   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8540   -4.3273    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7682   -5.7597    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9423   -6.5742    1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9431   -5.5825   -0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9722   -6.8981   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3536   -7.9732   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250   -7.7575    0.5019 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  2  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
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 20 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  2  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
 48 49  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
  2 53  1  0
  2 54  1  0
  3 55  1  0
  3 56  1  0
  4 57  1  0
  4 58  1  0
  5 59  1  0
  5 60  1  0
  6 61  1  0
  6 62  1  0
  7 63  1  0
  8 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
 10 68  1  0
 11 69  1  0
 11 70  1  0
 12 71  1  0
 12 72  1  0
 13 73  1  0
 13 74  1  0
 14 75  1  0
 15 76  1  0
 16 77  1  0
 16 78  1  0
 19 79  1  0
 20 80  1  6
 21 81  1  0
 21 82  1  0
 27 83  1  0
 27 84  1  0
 28 85  1  0
 28 86  1  0
 30 87  1  0
 30 88  1  0
 30 89  1  0
 31 90  1  0
 31 91  1  0
 31 92  1  0
 32 93  1  0
 32 94  1  0
 32 95  1  0
 33 96  1  6
 34 97  1  0
 35 98  1  0
 36 99  1  0
 37100  1  0
 37101  1  0
 38102  1  0
 38103  1  0
 39104  1  0
 39105  1  0
 40106  1  0
 40107  1  0
 41108  1  0
 41109  1  0
 42110  1  0
 42111  1  0
 43112  1  0
 43113  1  0
 44114  1  0
 44115  1  0
 45116  1  0
 45117  1  0
 46118  1  0
 46119  1  0
 47120  1  0
 47121  1  0
 48122  1  0
 48123  1  0
 49124  1  0
 49125  1  0
 49126  1  0
M  CHG  2  25  -1  29   1
M  END

HEADER    PROTEIN                                 13-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-FEB-20         0                                  
HETATM    1  C   UNK     0       7.649  -6.248   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      39.108  -4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.547  -7.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.655  -6.498   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.989  -5.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.316  -6.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.656  -5.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.983  -6.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.323  -5.530   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.650  -6.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.990  -5.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.317  -6.331   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.657  -5.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.985  -6.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.324  -5.593   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.652  -6.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.991  -5.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.319  -6.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.000  -4.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.660  -5.697   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.326  -5.656   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.986  -6.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.659  -5.635   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      28.974  -7.954   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      38.327  -5.718   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0      27.671  -4.095   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      32.233  -4.336   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      33.752  -7.015   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      34.332  -4.916   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      31.653  -6.435   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      32.993  -5.676   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      10.302  -8.724   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.636  -7.954   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.970  -8.724   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.303  -7.954   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.637  -8.724   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.971  -8.724   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.304  -7.954   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.638  -8.724   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.972  -7.954   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.305  -8.724   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.639  -7.954   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.973  -8.724   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      26.307  -7.954   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.640  -8.724   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      27.640 -10.264   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      24.973 -10.264   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       8.969  -7.954   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.635  -8.724   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   23                                                       
CONECT   19   20   25                                                       
CONECT   20   19   29                                                       
CONECT   21   22   30                                                       
CONECT   22   21   23   24                                                  
CONECT   23   18   22   26                                                  
CONECT   24   22   45                                                       
CONECT   25    2    3    4   19                                             
CONECT   26   23                                                            
CONECT   27   31                                                            
CONECT   28   31                                                            
CONECT   29   20   31                                                       
CONECT   30   21   31                                                       
CONECT   31   27   28   29   30                                             
CONECT   32   33   48                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   47                                                  
CONECT   44   43   45                                                       
CONECT   45   44   24   46                                                  
CONECT   46   45                                                            
CONECT   47   43                                                            
CONECT   48   32   49                                                       
CONECT   49   48                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

COMPND    HMDB0013463
HETATM    1  C1  UNL     1     -11.607  -4.867  -0.986  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.516  -4.629   0.176  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.968  -4.773   1.515  1.00  0.00           C  
HETATM    4  C4  UNL     1     -11.036  -3.978   2.251  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.719  -3.496   1.906  1.00  0.00           C  
HETATM    6  C6  UNL     1      -9.587  -2.286   1.070  1.00  0.00           C  
HETATM    7  C7  UNL     1     -10.157  -2.155  -0.245  1.00  0.00           C  
HETATM    8  C8  UNL     1      -9.467  -2.002  -1.345  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.996  -1.942  -1.392  1.00  0.00           C  
HETATM   10  C10 UNL     1      -7.525  -0.634  -1.978  1.00  0.00           C  
HETATM   11  C11 UNL     1      -6.026  -0.594  -1.997  1.00  0.00           C  
HETATM   12  C12 UNL     1      -5.472  -0.657  -0.610  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.921  -0.587  -0.741  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.313  -0.618   0.613  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.649  -1.790   1.314  1.00  0.00           O  
HETATM   16  C15 UNL     1      -1.827  -0.530   0.581  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.363   0.722  -0.025  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.142   1.552  -0.503  1.00  0.00           O  
HETATM   19  N1  UNL     1       0.056   1.002  -0.065  1.00  0.00           N  
HETATM   20  C17 UNL     1       0.559   2.222  -0.659  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.070   3.080   0.496  1.00  0.00           C  
HETATM   22  O3  UNL     1       0.050   3.361   1.387  1.00  0.00           O  
HETATM   23  P1  UNL     1       0.631   4.297   2.675  1.00  0.00           P  
HETATM   24  O4  UNL     1       1.762   3.472   3.300  1.00  0.00           O  
HETATM   25  O5  UNL     1      -0.540   4.480   3.857  1.00  0.00           O1-
HETATM   26  O6  UNL     1       1.305   5.746   2.191  1.00  0.00           O  
HETATM   27  C19 UNL     1       0.400   6.563   1.507  1.00  0.00           C  
HETATM   28  C20 UNL     1       1.115   7.819   1.140  1.00  0.00           C  
HETATM   29  N2  UNL     1       0.269   8.761   0.415  1.00  0.00           N1+
HETATM   30  C21 UNL     1       0.005   8.186  -0.883  1.00  0.00           C  
HETATM   31  C22 UNL     1       0.916  10.044   0.266  1.00  0.00           C  
HETATM   32  C23 UNL     1      -0.976   8.870   1.150  1.00  0.00           C  
HETATM   33  C24 UNL     1       1.733   1.839  -1.536  1.00  0.00           C  
HETATM   34  O7  UNL     1       1.357   0.947  -2.499  1.00  0.00           O  
HETATM   35  C25 UNL     1       2.851   1.344  -0.690  1.00  0.00           C  
HETATM   36  C26 UNL     1       3.097   0.067  -0.524  1.00  0.00           C  
HETATM   37  C27 UNL     1       4.190  -0.464   0.300  1.00  0.00           C  
HETATM   38  C28 UNL     1       5.110   0.540   0.894  1.00  0.00           C  
HETATM   39  C29 UNL     1       5.977   1.272  -0.073  1.00  0.00           C  
HETATM   40  C30 UNL     1       6.947   0.317  -0.812  1.00  0.00           C  
HETATM   41  C31 UNL     1       7.837  -0.315   0.194  1.00  0.00           C  
HETATM   42  C32 UNL     1       8.828  -1.230  -0.487  1.00  0.00           C  
HETATM   43  C33 UNL     1       8.094  -2.330  -1.191  1.00  0.00           C  
HETATM   44  C34 UNL     1       9.070  -3.234  -1.884  1.00  0.00           C  
HETATM   45  C35 UNL     1      10.036  -3.832  -0.909  1.00  0.00           C  
HETATM   46  C36 UNL     1       9.319  -4.622   0.138  1.00  0.00           C  
HETATM   47  C37 UNL     1      10.320  -5.187   1.108  1.00  0.00           C  
HETATM   48  C38 UNL     1      11.290  -6.093   0.395  1.00  0.00           C  
HETATM   49  C39 UNL     1      10.569  -7.246  -0.266  1.00  0.00           C  
HETATM   50  H1  UNL     1     -10.529  -4.921  -0.710  1.00  0.00           H  
HETATM   51  H2  UNL     1     -11.722  -4.059  -1.723  1.00  0.00           H  
HETATM   52  H3  UNL     1     -11.898  -5.805  -1.530  1.00  0.00           H  
HETATM   53  H4  UNL     1     -13.055  -3.651   0.005  1.00  0.00           H  
HETATM   54  H5  UNL     1     -13.369  -5.385   0.056  1.00  0.00           H  
HETATM   55  H6  UNL     1     -12.916  -4.867   2.212  1.00  0.00           H  
HETATM   56  H7  UNL     1     -11.662  -5.914   1.599  1.00  0.00           H  
HETATM   57  H8  UNL     1     -11.651  -3.086   2.706  1.00  0.00           H  
HETATM   58  H9  UNL     1     -10.877  -4.566   3.271  1.00  0.00           H  
HETATM   59  H10 UNL     1      -9.115  -3.252   2.869  1.00  0.00           H  
HETATM   60  H11 UNL     1      -9.051  -4.337   1.491  1.00  0.00           H  
HETATM   61  H12 UNL     1     -10.080  -1.390   1.676  1.00  0.00           H  
HETATM   62  H13 UNL     1      -8.510  -1.891   1.100  1.00  0.00           H  
HETATM   63  H14 UNL     1     -11.268  -2.138  -0.404  1.00  0.00           H  
HETATM   64  H15 UNL     1      -9.989  -1.910  -2.318  1.00  0.00           H  
HETATM   65  H16 UNL     1      -7.607  -2.744  -2.097  1.00  0.00           H  
HETATM   66  H17 UNL     1      -7.477  -2.130  -0.457  1.00  0.00           H  
HETATM   67  H18 UNL     1      -7.875   0.209  -1.332  1.00  0.00           H  
HETATM   68  H19 UNL     1      -7.927  -0.475  -3.006  1.00  0.00           H  
HETATM   69  H20 UNL     1      -5.611  -1.431  -2.612  1.00  0.00           H  
HETATM   70  H21 UNL     1      -5.754   0.369  -2.512  1.00  0.00           H  
HETATM   71  H22 UNL     1      -5.738   0.244  -0.017  1.00  0.00           H  
HETATM   72  H23 UNL     1      -5.712  -1.534  -0.021  1.00  0.00           H  
HETATM   73  H24 UNL     1      -3.754   0.311  -1.335  1.00  0.00           H  
HETATM   74  H25 UNL     1      -3.681  -1.519  -1.335  1.00  0.00           H  
HETATM   75  H26 UNL     1      -3.734   0.264   1.191  1.00  0.00           H  
HETATM   76  H27 UNL     1      -3.568  -1.560   2.285  1.00  0.00           H  
HETATM   77  H28 UNL     1      -1.391  -1.428   0.070  1.00  0.00           H  
HETATM   78  H29 UNL     1      -1.441  -0.525   1.649  1.00  0.00           H  
HETATM   79  H30 UNL     1       0.749   0.342   0.329  1.00  0.00           H  
HETATM   80  H31 UNL     1      -0.175   2.761  -1.238  1.00  0.00           H  
HETATM   81  H32 UNL     1       1.882   2.559   1.019  1.00  0.00           H  
HETATM   82  H33 UNL     1       1.389   4.039   0.066  1.00  0.00           H  
HETATM   83  H34 UNL     1       0.067   5.990   0.615  1.00  0.00           H  
HETATM   84  H35 UNL     1      -0.488   6.787   2.134  1.00  0.00           H  
HETATM   85  H36 UNL     1       1.430   8.334   2.073  1.00  0.00           H  
HETATM   86  H37 UNL     1       1.974   7.600   0.467  1.00  0.00           H  
HETATM   87  H38 UNL     1       0.768   7.411  -1.123  1.00  0.00           H  
HETATM   88  H39 UNL     1      -0.981   7.709  -0.886  1.00  0.00           H  
HETATM   89  H40 UNL     1       0.127   8.976  -1.663  1.00  0.00           H  
HETATM   90  H41 UNL     1       1.606   9.965  -0.615  1.00  0.00           H  
HETATM   91  H42 UNL     1       0.160  10.797  -0.012  1.00  0.00           H  
HETATM   92  H43 UNL     1       1.417  10.382   1.180  1.00  0.00           H  
HETATM   93  H44 UNL     1      -1.570   7.970   0.895  1.00  0.00           H  
HETATM   94  H45 UNL     1      -0.710   8.800   2.224  1.00  0.00           H  
HETATM   95  H46 UNL     1      -1.521   9.808   0.913  1.00  0.00           H  
HETATM   96  H47 UNL     1       2.124   2.753  -2.061  1.00  0.00           H  
HETATM   97  H48 UNL     1       2.094   0.417  -2.892  1.00  0.00           H  
HETATM   98  H49 UNL     1       3.433   2.092  -0.189  1.00  0.00           H  
HETATM   99  H50 UNL     1       2.446  -0.655  -1.035  1.00  0.00           H  
HETATM  100  H51 UNL     1       3.731  -1.087   1.102  1.00  0.00           H  
HETATM  101  H52 UNL     1       4.813  -1.165  -0.322  1.00  0.00           H  
HETATM  102  H53 UNL     1       5.734   0.138   1.709  1.00  0.00           H  
HETATM  103  H54 UNL     1       4.431   1.310   1.401  1.00  0.00           H  
HETATM  104  H55 UNL     1       5.494   1.820  -0.878  1.00  0.00           H  
HETATM  105  H56 UNL     1       6.616   2.020   0.466  1.00  0.00           H  
HETATM  106  H57 UNL     1       6.312  -0.336  -1.404  1.00  0.00           H  
HETATM  107  H58 UNL     1       7.555   0.940  -1.503  1.00  0.00           H  
HETATM  108  H59 UNL     1       8.402   0.514   0.695  1.00  0.00           H  
HETATM  109  H60 UNL     1       7.265  -0.869   0.983  1.00  0.00           H  
HETATM  110  H61 UNL     1       9.372  -0.587  -1.240  1.00  0.00           H  
HETATM  111  H62 UNL     1       9.532  -1.603   0.287  1.00  0.00           H  
HETATM  112  H63 UNL     1       7.448  -2.845  -0.458  1.00  0.00           H  
HETATM  113  H64 UNL     1       7.377  -1.925  -1.954  1.00  0.00           H  
HETATM  114  H65 UNL     1       8.545  -4.011  -2.489  1.00  0.00           H  
HETATM  115  H66 UNL     1       9.655  -2.621  -2.631  1.00  0.00           H  
HETATM  116  H67 UNL     1      10.635  -3.020  -0.457  1.00  0.00           H  
HETATM  117  H68 UNL     1      10.770  -4.490  -1.473  1.00  0.00           H  
HETATM  118  H69 UNL     1       8.597  -3.990   0.704  1.00  0.00           H  
HETATM  119  H70 UNL     1       8.745  -5.445  -0.363  1.00  0.00           H  
HETATM  120  H71 UNL     1      10.854  -4.327   1.577  1.00  0.00           H  
HETATM  121  H72 UNL     1       9.768  -5.760   1.891  1.00  0.00           H  
HETATM  122  H73 UNL     1      11.942  -6.574   1.182  1.00  0.00           H  
HETATM  123  H74 UNL     1      11.943  -5.582  -0.317  1.00  0.00           H  
HETATM  124  H75 UNL     1       9.972  -6.898  -1.108  1.00  0.00           H  
HETATM  125  H76 UNL     1      11.354  -7.973  -0.588  1.00  0.00           H  
HETATM  126  H77 UNL     1       9.925  -7.758   0.502  1.00  0.00           H  
CONECT    1    2   50   51   52
CONECT    2    3   53   54
CONECT    3    4   55   56
CONECT    4    5   57   58
CONECT    5    6   59   60
CONECT    6    7   61   62
CONECT    7    8    8   63
CONECT    8    9   64
CONECT    9   10   65   66
CONECT   10   11   67   68
CONECT   11   12   69   70
CONECT   12   13   71   72
CONECT   13   14   73   74
CONECT   14   15   16   75
CONECT   15   76
CONECT   16   17   77   78
CONECT   17   18   18   19
CONECT   19   20   79
CONECT   20   21   33   80
CONECT   21   22   81   82
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   26   27
CONECT   27   28   83   84
CONECT   28   29   85   86
CONECT   29   30   31   32
CONECT   30   87   88   89
CONECT   31   90   91   92
CONECT   32   93   94   95
CONECT   33   34   35   96
CONECT   34   97
CONECT   35   36   36   98
CONECT   36   37   99
CONECT   37   38  100  101
CONECT   38   39  102  103
CONECT   39   40  104  105
CONECT   40   41  106  107
CONECT   41   42  108  109
CONECT   42   43  110  111
CONECT   43   44  112  113
CONECT   44   45  114  115
CONECT   45   46  116  117
CONECT   46   47  118  119
CONECT   47   48  120  121
CONECT   48   49  122  123
CONECT   49  124  125  126
END

HMDB0013463
     RDKit          3D
SM(d18:0/16:1(9Z)(OH))
126125  0  0  0  0  0  0  0  0999 V2000
  -11.6069   -4.8668   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5159   -4.6295    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9685   -4.7729    1.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0357   -3.9784    2.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7186   -3.4964    1.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5870   -2.2858    1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1574   -2.1554   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4675   -2.0025   -1.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9961   -1.9424   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5251   -0.6339   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0256   -0.5945   -1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716   -0.6574   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214   -0.5866   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -0.6183    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -1.7900    1.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.5297    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3628    0.7222   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    1.5520   -0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    1.0016   -0.0648 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    2.2223   -0.6592 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0702    3.0803    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    3.3607    1.3865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309    4.2966    2.6746 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7617    3.4721    3.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404    4.4804    3.8573 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3048    5.7463    2.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    6.5630    1.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    7.8191    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    8.7612    0.4146 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0053    8.1865   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   10.0436    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757    8.8697    1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    1.8393   -1.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3569    0.9471   -2.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    1.3439   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971    0.0666   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.4644    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    0.5397    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765    1.2724   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9468    0.3173   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373   -0.3150    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.2301   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0940   -2.3304   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0696   -3.2345   -1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0360   -3.8319   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3188   -4.6217    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3199   -5.1870    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2903   -6.0931    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5691   -7.2458   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5291   -4.9211   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7221   -4.0593   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8981   -5.8052   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0549   -3.6507    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3686   -5.3846    0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9165   -4.8674    2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6619   -5.9142    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6509   -3.0856    2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770   -4.5665    3.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1152   -3.2525    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0509   -4.3375    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0802   -1.3900    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5104   -1.8909    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2684   -2.1380   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9886   -1.9099   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6070   -2.7439   -2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4772   -2.1304   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8753    0.2088   -1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9266   -0.4746   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113   -1.4312   -2.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7542    0.3688   -2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    0.2440   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121   -1.5336   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7542    0.3107   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -1.5185   -1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.2642    1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683   -1.5598    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -1.4278    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.5248    1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    0.3419    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1745    2.7610   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817    2.5588    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    4.0391    0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671    5.9905    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880    6.7869    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    8.3343    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    7.5998    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    7.4108   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    7.7094   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1273    8.9756   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    9.9650   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598   10.7971   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   10.3819    1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698    7.9701    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    8.7999    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    9.8081    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    2.7530   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.4175   -2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4332    2.0917   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4462   -0.6555   -1.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7312   -1.0874    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129   -1.1653   -0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345    0.1377    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307    1.3100    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4940    1.8202   -0.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163    2.0200    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3122   -0.3358   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551    0.9405   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023    0.5144    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2650   -0.8687    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3721   -0.5871   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5319   -1.6034    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4483   -2.8450   -0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774   -1.9249   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5447   -4.0109   -2.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6550   -2.6214   -2.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6345   -3.0199   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7699   -4.4901   -1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5967   -3.9901    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7453   -5.4449   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8540   -4.3273    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7682   -5.7597    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9423   -6.5742    1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9431   -5.5825   -0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9722   -6.8981   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3536   -7.9732   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250   -7.7575    0.5019 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  2  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
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 20 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  2  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
 48 49  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
  2 53  1  0
  2 54  1  0
  3 55  1  0
  3 56  1  0
  4 57  1  0
  4 58  1  0
  5 59  1  0
  5 60  1  0
  6 61  1  0
  6 62  1  0
  7 63  1  0
  8 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
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 20 80  1  6
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 27 83  1  0
 27 84  1  0
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 28 86  1  0
 30 87  1  0
 30 88  1  0
 30 89  1  0
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 31 91  1  0
 31 92  1  0
 32 93  1  0
 32 94  1  0
 32 95  1  0
 33 96  1  6
 34 97  1  0
 35 98  1  0
 36 99  1  0
 37100  1  0
 37101  1  0
 38102  1  0
 38103  1  0
 39104  1  0
 39105  1  0
 40106  1  0
 40107  1  0
 41108  1  0
 41109  1  0
 42110  1  0
 42111  1  0
 43112  1  0
 43113  1  0
 44114  1  0
 44115  1  0
 45116  1  0
 45117  1  0
 46118  1  0
 46119  1  0
 47120  1  0
 47121  1  0
 48122  1  0
 48123  1  0
 49124  1  0
 49125  1  0
 49126  1  0
M  CHG  2  25  -1  29   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C16:1-OH Sphingomyelin	ChEBI
Hydroxysphingomyeline C16:1	ChEBI
N-[(9Z)-3-Hydroxyhexadec-9-enoyl]sphing-4-enine-1-phosphocholine	ChEBI
SM(D18:1/16:1(9Z)(OH))	ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/16:1(9Z)(OH))	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₃₉H₇₇N₂O₇P

Average Molecular Weight

717.0116

Monoisotopic Molecular Weight

716.54683934

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1

InChI Key

LPHMSPONPQCKTL-FKUNDBCPSA-N

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

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 28278231)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Saliva (HMDB: HMDB0013463)
Cerebrospinal fluid (HMDB: HMDB0013463)

Cell

All cells and tissues (HMDB: HMDB0013463)

Cellular substructure

Membrane (HMDB: HMDB0013463)
Endosome (HMDB: HMDB0013463)
Extracellular (HMDB: HMDB0013463)
Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)
Myelin sheath (HMDB: HMDB0013463)
Cell membrane (HMDB: HMDB0013463)
Axon (HMDB: HMDB0013463)

Organelle

Endoplasmic reticulum (PMID: 9009829)

Nervous system (HMDB: HMDB0013463)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Organ

Brain (HMDB: HMDB0013463)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013463)

Source

Endogenous

Endogenous (HMDB: HMDB0013463)

Animal

Animal (HMDB: HMDB0013463)

Exogenous

Food

Food (HMDB: HMDB0013463)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Exogenous (HMDB: HMDB0013463)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013463)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013463)

Lipid metabolism pathway (HMDB: HMDB0013463)

Cellular process

Cell signaling (HMDB: HMDB0013463)
Cell signaling (PMID: 8086039)

Biochemical process

Lipid transport (HMDB: HMDB0013463)

Role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.8e-05 g/L	ALOGPS
logP	4.38	ALOGPS
logP	5.38	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.15 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	216.57 m³·mol⁻¹	ChemAxon
Polarizability	87.13 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	269.445	30932474
DeepCCS	[M-H]-	267.62	30932474
DeepCCS	[M-2H]-	300.863	30932474
DeepCCS	[M+Na]+	275.051	30932474
AllCCS	[M+H]+	282.7	32859911
AllCCS	[M+H-H2O]+	282.5	32859911
AllCCS	[M+NH4]+	282.9	32859911
AllCCS	[M+Na]+	282.9	32859911
AllCCS	[M-H]-	274.5	32859911
AllCCS	[M+Na-2H]-	278.7	32859911
AllCCS	[M+HCOO]-	283.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
SM(d18:0/16:1(9Z)(OH))	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC	4773.5	Standard polar	33892256
SM(d18:0/16:1(9Z)(OH))	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC	3894.5	Standard non polar	33892256
SM(d18:0/16:1(9Z)(OH))	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC	4986.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysphingomyeline C16:1 GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Positive-QTOF	splash10-00m1-5020195100-75c4428f308b70e492a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Positive-QTOF	splash10-00lr-2140191000-1a1ed63feed3f152dcdb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Positive-QTOF	splash10-001r-8190032000-c1f385095a959e7e14be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Negative-QTOF	splash10-014i-0010004900-03516550d63a4b14a21d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Negative-QTOF	splash10-02u0-1172149200-27f568a6bfc192cf91f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Negative-QTOF	splash10-00or-9183120000-1d21406c331bfb554143	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Positive-QTOF	splash10-000i-0000011900-4aa51f66c591f10a45d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Positive-QTOF	splash10-0a50-0000092900-3dc7f7c1babd46a42d93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Positive-QTOF	splash10-0a4i-0000091100-d0b9a75fac9ff500e6c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Negative-QTOF	splash10-014i-0000000900-282d41e16428007043d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Negative-QTOF	splash10-014i-0020003900-41188580822b70887c3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Negative-QTOF	splash10-004i-9282000000-d0383bad10de3658c4d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Positive-QTOF	splash10-00di-0000011900-913b25a99091d7742381	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Positive-QTOF	splash10-00do-0000092900-807f48801e76940db556	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Positive-QTOF	splash10-0006-0000091100-11de640103dd3b340f84	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 10V, Positive-QTOF	splash10-0159-0600000900-a4544d9a891eec8a2b0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 20V, Positive-QTOF	splash10-0159-0600000900-a4544d9a891eec8a2b0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysphingomyeline C16:1 40V, Positive-QTOF	splash10-001i-0900001100-59b07f8576eaafa65901	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.93 (1.63-2.35) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	1.1-8.2 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	3.01 (2.33-3.81) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	16.6 +/- 3.36 uM	Adult (>18 years old)	Both	Normal	28278231	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.020 +/- 0.007 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected and Quantified	0.24 +/- 0.29 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.27 +/- 0.4 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.020 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.0-0.24 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.0-0.29) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.0-0.02) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.0012 +/- 0.0014 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0006 (0.0001-0.0023) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.42 +/- 0.68 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	2.55 +/- 0.70 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	4.4412 (0.9153) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Urine	Detected and Quantified	0.001 +/- 0.0019 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.001 +/- 0.0013 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

601665 (Obesity)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029463

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingomyelin

METLIN ID

Not Available

PubChem Compound

53481779

PDB ID

Not Available

ChEBI ID

90007

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
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 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 52 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:: GBGT1
Uniprot ID:: Q8N5D6
Molecular weight:: 40126.9

Enzyme Details

2. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase

General function:: Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:: Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:: PIGL
Uniprot ID:: Q9Y2B2
Molecular weight:: 28530.965

Enzyme Details

3. Phosphatidylcholine:ceramide cholinephosphotransferase 2

General function:: Involved in catalytic activity
Specific function:: Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Required for cell growth
Gene Name:: SGMS2
Uniprot ID:: Q8NHU3
Molecular weight:: 42279.8

Enzyme Details

4. Phosphatidylcholine:ceramide cholinephosphotransferase 1

General function:: Involved in catalytic activity
Specific function:: Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Suppresses BAX-mediated apoptosis and also prevents cell death in response to stimuli such as hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. May protect against cell death by reversing the stress-inducible increase in levels of proapoptotic ceramide. Required for cell growth
Gene Name:: SGMS1
Uniprot ID:: Q86VZ5
Molecular weight:: 49207.3

Enzyme Details

5. Sphingomyelin phosphodiesterase

General function:: Involved in hydrolase activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:: SMPD1
Uniprot ID:: P17405
Molecular weight:: 69935.53

Enzyme Details

6. Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1

General function:: Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:: Involved in the biosynthesis of L2/HNK-1 carbohydrate epitope on glycoproteins. Can also play a role in glycosaminoglycan biosynthesis. Substrates include asialo-orosomucoid (ASOR), asialo-fetuin, and asialo-neural cell adhesion molecule. Requires sphingomyelin for activity: stearoyl-sphingomyelin was the most effective, followed by palmitoyl-sphingomyelin and lignoceroyl-sphingomyelin. Activity was demonstrated only for sphingomyelin with a saturated fatty acid and not for that with an unsaturated fatty acid, regardless of the length of the acyl group (By similarity).
Gene Name:: B3GAT1
Uniprot ID:: Q9P2W7
Molecular weight:: 38255.675

Enzyme Details

7. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q

General function:: Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:: Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:: PIGQ
Uniprot ID:: Q9BRB3
Molecular weight:: 65343.25

Enzyme Details

8. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A

General function:: Involved in biosynthetic process
Specific function:: Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:: PIGA
Uniprot ID:: P37287
Molecular weight:: 54126.065

Enzyme Details

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit H

General function:: Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:: Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:: PIGH
Uniprot ID:: Q14442
Molecular weight:: 21080.415

Enzyme Details

10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit P

General function:: Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:: Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:: PIGP
Uniprot ID:: P57054
Molecular weight:: 18089.055

Only showing the first 10 proteins. There are 52 proteins in total.

Show all enzymes and transporters

Showing metabocard for Hydroxysphingomyeline C16:1 (HMDB0013463)

MOL for HMDB0013463 (Hydroxysphingomyeline C16:1)

3D MOL for HMDB0013463 (Hydroxysphingomyeline C16:1)

3D SDF for HMDB0013463 (Hydroxysphingomyeline C16:1)

3D-SDF for HMDB0013463 (Hydroxysphingomyeline C16:1)

PDB for HMDB0013463 (Hydroxysphingomyeline C16:1)

3D PDB for HMDB0013463 (Hydroxysphingomyeline C16:1)

SMILES for HMDB0013463 (Hydroxysphingomyeline C16:1)

INCHI for HMDB0013463 (Hydroxysphingomyeline C16:1)

Structure for HMDB0013463 (Hydroxysphingomyeline C16:1)

3D Structure for HMDB0013463 (Hydroxysphingomyeline C16:1)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes