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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-03-24 16:22:18 UTC

Update Date

2022-11-30 19:04:10 UTC

HMDB ID

HMDB0012096

Secondary Accession Numbers

HMDB12096

Metabolite Identification

Common Name

SM(d18:1/12:0)

Description

SM(d18:1/12:0) is a sphingomyelin (SM). Sphingomyelins are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). SM is the major sphingolipid in mammals it is found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. SM 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. In terms of its appearance and structure, SM(d18:1/12:0) consists of an unsaturated 18-carbon sphingoid base with an attached saturated dodecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).

Structure

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

  Mrv0541 02241203382D          

 44 43  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
    6.9488   -4.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9508   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1145   -3.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2439   -3.4814    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
    7.6600   -4.6122    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
    8.3776   -4.2053    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
    9.0889   -4.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9555   -3.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8066   -4.2166    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
   10.5178   -4.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3840   -3.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1017   -2.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8130   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5307   -2.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2354   -4.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2418   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595   -2.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9467   -4.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6707   -3.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6644   -4.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3884   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3756   -4.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0997   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0932   -4.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8214   -2.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1037   -3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2462   -3.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5286   -3.4368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8173   -3.0186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8042   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5219   -4.2613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5327   -3.0633    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   14.8237   -2.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7978   -5.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2680   -2.3230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.0817   -3.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3925   -2.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9572   -3.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6749   -3.0407    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  2  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
 32 33  1  0  0  0  0
 32 43  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  6  0  0  0
 34 38  1  1  0  0  0
 35 36  1  0  0  0  0
 35 39  2  0  0  0  0
 40 44  1  0  0  0  0
 41 44  2  0  0  0  0
 42 44  1  0  0  0  0
 43 44  1  0  0  0  0
M  CHG  2  37   1  40  -1
M  END

HMDB0012096
     RDKit          3D
SM(d18:1/12:0)
115114  0  0  0  0  0  0  0  0999 V2000
    3.5934    5.9474    5.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    5.2614    3.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    6.0455    2.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979    5.6611    1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266    5.6520    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889    4.7601    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5226    4.8029   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    4.3677   -1.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229    4.3987   -3.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1224    4.0351   -4.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499    2.7354   -4.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    2.1852   -3.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    3.0374   -3.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104    2.4137   -3.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022    1.2394   -2.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0233    0.7159   -1.6800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0285    0.3210   -2.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701   -0.4101   -0.7611 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4846    0.0113    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -1.0039    1.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -0.5871    2.1510 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4016    0.5075    3.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730   -0.0573    1.3540 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.3922   -1.8773    3.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536   -2.1070    4.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -3.2697    4.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7032   -3.5677    5.9343 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.8984   -2.3909    6.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971   -4.5336    5.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -4.1902    7.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -1.5828   -1.5153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915   -2.8468   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -2.8723   -0.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -4.0471   -2.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -5.2791   -1.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -5.1302   -2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5549   -6.4029   -1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088   -6.1851   -2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535   -5.0859   -1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -4.9770   -1.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8135   -3.8787   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2646   -3.7611   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8828   -2.6456   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1953   -1.3241   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092    6.8580    5.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9716    5.2191    5.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    6.1719    5.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592    4.2142    3.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    5.2952    3.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254    6.1501    3.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    7.1167    2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4943    6.3048    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    4.6344    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    6.7403    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    5.4991   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562    5.1913    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3225    3.7449    0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9192    5.8014   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    4.0974   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0041    5.1553   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425    3.4123   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    3.7976   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1337    5.4621   -3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9427    4.2106   -5.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747    4.8453   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3176    1.8952   -4.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925    2.7605   -5.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    1.7130   -2.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903    1.2568   -4.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3929    4.0909   -3.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829    3.1555   -4.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1741    3.0143   -2.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.6297   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010    1.5927   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -0.4664   -3.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -0.6428   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969    0.8775    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    0.2319   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -1.2360    4.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -2.4225    3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553   -2.9938    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095   -4.2013    4.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -2.0402    5.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -1.6039    6.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -2.6233    6.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -5.3063    4.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754   -4.9571    6.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -3.9979    4.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -4.9559    6.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211   -4.7411    7.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5928   -3.4362    7.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -1.5152   -2.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -3.8769   -3.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5349   -4.3080   -1.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373   -6.0974   -2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285   -5.6931   -0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -4.3423   -1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -4.8687   -3.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -6.5724   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -7.2604   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1744   -5.9445   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178   -7.1057   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -4.0785   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6117   -5.3418   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2362   -4.7576   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6465   -5.9215   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893   -4.1081    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3491   -2.9011   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8399   -4.6801   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4122   -3.4890   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7525   -2.8646    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38101  1  0
 38102  1  0
 39103  1  0
 39104  1  0
 40105  1  0
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 41107  1  0
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 42109  1  0
 42110  1  0
 43111  1  0
 43112  1  0
 44113  1  0
 44114  1  0
 44115  1  0
M  CHG  2  23  -1  27   1
M  END

  Mrv0541 02241203382D          

 44 43  0  0  1  0            999 V2000
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  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
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 41 44  2  0  0  0  0
 42 44  1  0  0  0  0
 43 44  1  0  0  0  0
M  CHG  2  37   1  40  -1
M  END
> <DATABASE_ID>
HMDB0012096

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C35H71N2O6P/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/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1

> <INCHI_KEY>
HZCLJRFPXMKWHR-FEBLJDHQSA-N

> <FORMULA>
C35H71N2O6P

> <MOLECULAR_WEIGHT>
646.9218

> <EXACT_MASS>
646.504974526

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
79.95925348353897

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
6.28712717619508

> <ALOGPS_LOGS>
-7.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.499201320641198

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8709150288593719

> <JCHEM_PKA_STRONGEST_BASIC>
0.011796153944252485

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
195.53790000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.63e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012096
     RDKit          3D
SM(d18:1/12:0)
115114  0  0  0  0  0  0  0  0999 V2000
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    4.2092    6.8580    5.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1833   -1.2360    4.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -2.4225    3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553   -2.9938    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095   -4.2013    4.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -2.0402    5.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -1.6039    6.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -2.6233    6.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -5.3063    4.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754   -4.9571    6.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -3.9979    4.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -4.9559    6.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211   -4.7411    7.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5928   -3.4362    7.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -1.5152   -2.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -3.8769   -3.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5349   -4.3080   -1.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373   -6.0974   -2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285   -5.6931   -0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -4.3423   -1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -4.8687   -3.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -6.5724   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -7.2604   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1744   -5.9445   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178   -7.1057   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -4.0785   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6117   -5.3418   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2362   -4.7576   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6465   -5.9215   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893   -4.1081    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3491   -2.9011   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8399   -4.6801   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4122   -3.4890   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7525   -2.8646    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9677   -2.5273   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933   -1.2422   -0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8836   -0.4597   -0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9124   -1.3589   -1.7896 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  2  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 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 18 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
  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
 15 73  1  0
 16 74  1  1
 17 75  1  0
 18 76  1  1
 19 77  1  0
 19 78  1  0
 25 79  1  0
 25 80  1  0
 26 81  1  0
 26 82  1  0
 28 83  1  0
 28 84  1  0
 28 85  1  0
 29 86  1  0
 29 87  1  0
 29 88  1  0
 30 89  1  0
 30 90  1  0
 30 91  1  0
 31 92  1  0
 34 93  1  0
 34 94  1  0
 35 95  1  0
 35 96  1  0
 36 97  1  0
 36 98  1  0
 37 99  1  0
 37100  1  0
 38101  1  0
 38102  1  0
 39103  1  0
 39104  1  0
 40105  1  0
 40106  1  0
 41107  1  0
 41108  1  0
 42109  1  0
 42110  1  0
 43111  1  0
 43112  1  0
 44113  1  0
 44114  1  0
 44115  1  0
M  CHG  2  23  -1  27   1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.649  -6.248   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.971  -7.829   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.108  -4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      37.547  -7.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      39.655  -6.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.989  -5.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.299  -8.609   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.316  -6.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.638  -7.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.656  -5.509   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.966  -8.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.984  -6.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.306  -7.871   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.323  -5.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.633  -8.651   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.650  -6.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.990  -5.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.318  -6.331   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.657  -5.571   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.973  -7.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.985  -6.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.324  -5.593   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.301  -8.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.652  -6.373   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.640  -7.913   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.992  -5.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.968  -8.694   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.319  -6.394   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.307  -7.934   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      37.000  -4.938   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      35.660  -5.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.326  -5.656   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.987  -6.415   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.659  -5.635   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.635  -8.714   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      28.974  -7.954   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      38.328  -5.718   0.000  0.00  0.00           N+1
HETATM   38  O   UNK     0      27.671  -4.095   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      27.623 -10.254   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      32.234  -4.336   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0      33.753  -7.015   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      34.333  -4.916   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      31.653  -6.435   0.000  0.00  0.00           O+0
HETATM   44  P   UNK     0      32.993  -5.676   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

COMPND    HMDB0012096
HETATM    1  C1  UNL     1       3.593   5.947   5.180  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.610   5.261   3.782  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.686   6.045   2.946  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.398   5.661   1.558  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.427   5.652   0.503  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.589   4.760   0.646  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.523   4.803  -0.564  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.774   4.368  -1.843  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.723   4.399  -3.007  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.122   4.035  -4.286  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.550   2.735  -4.578  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.413   2.185  -3.806  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.194   3.037  -3.799  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.110   2.414  -3.028  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.202   1.239  -2.440  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.023   0.716  -1.680  1.00  0.00           C  
HETATM   17  O1  UNL     1      -1.029   0.321  -2.495  1.00  0.00           O  
HETATM   18  C17 UNL     1       0.370  -0.410  -0.761  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.485   0.011   0.183  1.00  0.00           C  
HETATM   20  O2  UNL     1       1.756  -1.004   1.068  1.00  0.00           O  
HETATM   21  P1  UNL     1       2.991  -0.587   2.151  1.00  0.00           P  
HETATM   22  O3  UNL     1       2.402   0.507   3.044  1.00  0.00           O  
HETATM   23  O4  UNL     1       4.373  -0.057   1.354  1.00  0.00           O1-
HETATM   24  O5  UNL     1       3.392  -1.877   3.162  1.00  0.00           O  
HETATM   25  C19 UNL     1       2.354  -2.107   4.061  1.00  0.00           C  
HETATM   26  C20 UNL     1       2.734  -3.270   4.972  1.00  0.00           C  
HETATM   27  N1  UNL     1       1.703  -3.568   5.934  1.00  0.00           N1+
HETATM   28  C21 UNL     1       0.898  -2.391   6.207  1.00  0.00           C  
HETATM   29  C22 UNL     1       0.797  -4.534   5.297  1.00  0.00           C  
HETATM   30  C23 UNL     1       2.192  -4.190   7.128  1.00  0.00           C  
HETATM   31  N2  UNL     1       0.733  -1.583  -1.515  1.00  0.00           N  
HETATM   32  C24 UNL     1       0.091  -2.847  -1.323  1.00  0.00           C  
HETATM   33  O6  UNL     1      -0.810  -2.872  -0.450  1.00  0.00           O  
HETATM   34  C25 UNL     1       0.437  -4.047  -2.073  1.00  0.00           C  
HETATM   35  C26 UNL     1      -0.325  -5.279  -1.767  1.00  0.00           C  
HETATM   36  C27 UNL     1      -1.787  -5.130  -2.043  1.00  0.00           C  
HETATM   37  C28 UNL     1      -2.555  -6.403  -1.731  1.00  0.00           C  
HETATM   38  C29 UNL     1      -4.009  -6.185  -2.035  1.00  0.00           C  
HETATM   39  C30 UNL     1      -4.654  -5.086  -1.252  1.00  0.00           C  
HETATM   40  C31 UNL     1      -6.120  -4.977  -1.638  1.00  0.00           C  
HETATM   41  C32 UNL     1      -6.813  -3.879  -0.868  1.00  0.00           C  
HETATM   42  C33 UNL     1      -8.265  -3.761  -1.236  1.00  0.00           C  
HETATM   43  C34 UNL     1      -8.883  -2.646  -0.424  1.00  0.00           C  
HETATM   44  C35 UNL     1      -8.195  -1.324  -0.701  1.00  0.00           C  
HETATM   45  H1  UNL     1       4.209   6.858   5.082  1.00  0.00           H  
HETATM   46  H2  UNL     1       3.972   5.219   5.898  1.00  0.00           H  
HETATM   47  H3  UNL     1       2.546   6.172   5.424  1.00  0.00           H  
HETATM   48  H4  UNL     1       3.259   4.214   3.909  1.00  0.00           H  
HETATM   49  H5  UNL     1       4.655   5.295   3.482  1.00  0.00           H  
HETATM   50  H6  UNL     1       1.725   6.150   3.547  1.00  0.00           H  
HETATM   51  H7  UNL     1       3.079   7.117   2.919  1.00  0.00           H  
HETATM   52  H8  UNL     1       1.494   6.305   1.227  1.00  0.00           H  
HETATM   53  H9  UNL     1       1.873   4.634   1.587  1.00  0.00           H  
HETATM   54  H10 UNL     1       3.773   6.740   0.386  1.00  0.00           H  
HETATM   55  H11 UNL     1       2.877   5.499  -0.474  1.00  0.00           H  
HETATM   56  H12 UNL     1       5.256   5.191   1.458  1.00  0.00           H  
HETATM   57  H13 UNL     1       4.322   3.745   0.953  1.00  0.00           H  
HETATM   58  H14 UNL     1       5.919   5.801  -0.717  1.00  0.00           H  
HETATM   59  H15 UNL     1       6.348   4.097  -0.351  1.00  0.00           H  
HETATM   60  H16 UNL     1       4.004   5.155  -2.069  1.00  0.00           H  
HETATM   61  H17 UNL     1       4.342   3.412  -1.584  1.00  0.00           H  
HETATM   62  H18 UNL     1       6.617   3.798  -2.717  1.00  0.00           H  
HETATM   63  H19 UNL     1       6.134   5.462  -3.011  1.00  0.00           H  
HETATM   64  H20 UNL     1       5.943   4.211  -5.077  1.00  0.00           H  
HETATM   65  H21 UNL     1       4.375   4.845  -4.618  1.00  0.00           H  
HETATM   66  H22 UNL     1       5.318   1.895  -4.630  1.00  0.00           H  
HETATM   67  H23 UNL     1       4.193   2.761  -5.664  1.00  0.00           H  
HETATM   68  H24 UNL     1       3.666   1.713  -2.842  1.00  0.00           H  
HETATM   69  H25 UNL     1       3.090   1.257  -4.422  1.00  0.00           H  
HETATM   70  H26 UNL     1       2.393   4.091  -3.492  1.00  0.00           H  
HETATM   71  H27 UNL     1       1.783   3.155  -4.850  1.00  0.00           H  
HETATM   72  H28 UNL     1       0.174   3.014  -2.968  1.00  0.00           H  
HETATM   73  H29 UNL     1       2.085   0.630  -2.484  1.00  0.00           H  
HETATM   74  H30 UNL     1      -0.401   1.593  -1.088  1.00  0.00           H  
HETATM   75  H31 UNL     1      -0.780  -0.466  -3.070  1.00  0.00           H  
HETATM   76  H32 UNL     1      -0.501  -0.643  -0.127  1.00  0.00           H  
HETATM   77  H33 UNL     1       1.097   0.878   0.752  1.00  0.00           H  
HETATM   78  H34 UNL     1       2.410   0.232  -0.377  1.00  0.00           H  
HETATM   79  H35 UNL     1       2.183  -1.236   4.694  1.00  0.00           H  
HETATM   80  H36 UNL     1       1.469  -2.423   3.462  1.00  0.00           H  
HETATM   81  H37 UNL     1       3.655  -2.994   5.555  1.00  0.00           H  
HETATM   82  H38 UNL     1       2.909  -4.201   4.380  1.00  0.00           H  
HETATM   83  H39 UNL     1       0.407  -2.040   5.291  1.00  0.00           H  
HETATM   84  H40 UNL     1       1.564  -1.604   6.596  1.00  0.00           H  
HETATM   85  H41 UNL     1       0.080  -2.623   6.929  1.00  0.00           H  
HETATM   86  H42 UNL     1       1.379  -5.306   4.760  1.00  0.00           H  
HETATM   87  H43 UNL     1       0.075  -4.957   6.000  1.00  0.00           H  
HETATM   88  H44 UNL     1       0.212  -3.998   4.504  1.00  0.00           H  
HETATM   89  H45 UNL     1       2.919  -4.956   6.845  1.00  0.00           H  
HETATM   90  H46 UNL     1       1.321  -4.741   7.589  1.00  0.00           H  
HETATM   91  H47 UNL     1       2.593  -3.436   7.833  1.00  0.00           H  
HETATM   92  H48 UNL     1       1.489  -1.515  -2.228  1.00  0.00           H  
HETATM   93  H49 UNL     1       0.339  -3.877  -3.190  1.00  0.00           H  
HETATM   94  H50 UNL     1       1.535  -4.308  -1.960  1.00  0.00           H  
HETATM   95  H51 UNL     1       0.037  -6.097  -2.459  1.00  0.00           H  
HETATM   96  H52 UNL     1      -0.129  -5.693  -0.754  1.00  0.00           H  
HETATM   97  H53 UNL     1      -2.222  -4.342  -1.408  1.00  0.00           H  
HETATM   98  H54 UNL     1      -1.908  -4.869  -3.135  1.00  0.00           H  
HETATM   99  H55 UNL     1      -2.463  -6.572  -0.641  1.00  0.00           H  
HETATM  100  H56 UNL     1      -2.203  -7.260  -2.327  1.00  0.00           H  
HETATM  101  H57 UNL     1      -4.174  -5.944  -3.123  1.00  0.00           H  
HETATM  102  H58 UNL     1      -4.618  -7.106  -1.843  1.00  0.00           H  
HETATM  103  H59 UNL     1      -4.207  -4.078  -1.420  1.00  0.00           H  
HETATM  104  H60 UNL     1      -4.612  -5.342  -0.178  1.00  0.00           H  
HETATM  105  H61 UNL     1      -6.236  -4.758  -2.717  1.00  0.00           H  
HETATM  106  H62 UNL     1      -6.647  -5.922  -1.430  1.00  0.00           H  
HETATM  107  H63 UNL     1      -6.789  -4.108   0.236  1.00  0.00           H  
HETATM  108  H64 UNL     1      -6.349  -2.901  -0.995  1.00  0.00           H  
HETATM  109  H65 UNL     1      -8.840  -4.680  -1.000  1.00  0.00           H  
HETATM  110  H66 UNL     1      -8.412  -3.489  -2.304  1.00  0.00           H  
HETATM  111  H67 UNL     1      -8.752  -2.865   0.657  1.00  0.00           H  
HETATM  112  H68 UNL     1      -9.968  -2.527  -0.623  1.00  0.00           H  
HETATM  113  H69 UNL     1      -7.293  -1.242  -0.096  1.00  0.00           H  
HETATM  114  H70 UNL     1      -8.884  -0.460  -0.565  1.00  0.00           H  
HETATM  115  H71 UNL     1      -7.912  -1.359  -1.790  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3   48   49
CONECT    3    4   50   51
CONECT    4    5   52   53
CONECT    5    6   54   55
CONECT    6    7   56   57
CONECT    7    8   58   59
CONECT    8    9   60   61
CONECT    9   10   62   63
CONECT   10   11   64   65
CONECT   11   12   66   67
CONECT   12   13   68   69
CONECT   13   14   70   71
CONECT   14   15   15   72
CONECT   15   16   73
CONECT   16   17   18   74
CONECT   17   75
CONECT   18   19   31   76
CONECT   19   20   77   78
CONECT   20   21
CONECT   21   22   22   23   24
CONECT   24   25
CONECT   25   26   79   80
CONECT   26   27   81   82
CONECT   27   28   29   30
CONECT   28   83   84   85
CONECT   29   86   87   88
CONECT   30   89   90   91
CONECT   31   32   92
CONECT   32   33   33   34
CONECT   34   35   93   94
CONECT   35   36   95   96
CONECT   36   37   97   98
CONECT   37   38   99  100
CONECT   38   39  101  102
CONECT   39   40  103  104
CONECT   40   41  105  106
CONECT   41   42  107  108
CONECT   42   43  109  110
CONECT   43   44  111  112
CONECT   44  113  114  115
END

HMDB0012096
     RDKit          3D
SM(d18:1/12:0)
115114  0  0  0  0  0  0  0  0999 V2000
    3.5934    5.9474    5.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    5.2614    3.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    6.0455    2.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979    5.6611    1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266    5.6520    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889    4.7601    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5226    4.8029   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    4.3677   -1.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7229    4.3987   -3.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1224    4.0351   -4.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499    2.7354   -4.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    2.1852   -3.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    3.0374   -3.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104    2.4137   -3.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022    1.2394   -2.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0233    0.7159   -1.6800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0285    0.3210   -2.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701   -0.4101   -0.7611 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4846    0.0113    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -1.0039    1.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -0.5871    2.1510 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4016    0.5075    3.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730   -0.0573    1.3540 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.3922   -1.8773    3.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3536   -2.1070    4.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -3.2697    4.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7032   -3.5677    5.9343 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.8984   -2.3909    6.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971   -4.5336    5.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -4.1902    7.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -1.5828   -1.5153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915   -2.8468   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -2.8723   -0.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -4.0471   -2.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250   -5.2791   -1.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -5.1302   -2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5549   -6.4029   -1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088   -6.1851   -2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535   -5.0859   -1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203   -4.9770   -1.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8135   -3.8787   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2646   -3.7611   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8828   -2.6456   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1953   -1.3241   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092    6.8580    5.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9716    5.2191    5.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    6.1719    5.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592    4.2142    3.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    5.2952    3.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254    6.1501    3.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    7.1167    2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4943    6.3048    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    4.6344    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    6.7403    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    5.4991   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562    5.1913    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3225    3.7449    0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9192    5.8014   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479    4.0974   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0041    5.1553   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3425    3.4123   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    3.7976   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1337    5.4621   -3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9427    4.2106   -5.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747    4.8453   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3176    1.8952   -4.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925    2.7605   -5.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660    1.7130   -2.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903    1.2568   -4.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3929    4.0909   -3.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829    3.1555   -4.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1741    3.0143   -2.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.6297   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010    1.5927   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -0.4664   -3.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007   -0.6428   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969    0.8775    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    0.2319   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -1.2360    4.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -2.4225    3.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553   -2.9938    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095   -4.2013    4.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -2.0402    5.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5635   -1.6039    6.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -2.6233    6.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -5.3063    4.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754   -4.9571    6.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -3.9979    4.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -4.9559    6.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211   -4.7411    7.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5928   -3.4362    7.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -1.5152   -2.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388   -3.8769   -3.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5349   -4.3080   -1.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373   -6.0974   -2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285   -5.6931   -0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -4.3423   -1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -4.8687   -3.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -6.5724   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -7.2604   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1744   -5.9445   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178   -7.1057   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -4.0785   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6117   -5.3418   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2362   -4.7576   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6465   -5.9215   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893   -4.1081    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3491   -2.9011   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8399   -4.6801   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4122   -3.4890   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7525   -2.8646    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9677   -2.5273   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933   -1.2422   -0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8836   -0.4597   -0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9124   -1.3589   -1.7896 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  2  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 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 18 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
  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
 15 73  1  0
 16 74  1  1
 17 75  1  0
 18 76  1  1
 19 77  1  0
 19 78  1  0
 25 79  1  0
 25 80  1  0
 26 81  1  0
 26 82  1  0
 28 83  1  0
 28 84  1  0
 28 85  1  0
 29 86  1  0
 29 87  1  0
 29 88  1  0
 30 89  1  0
 30 90  1  0
 30 91  1  0
 31 92  1  0
 34 93  1  0
 34 94  1  0
 35 95  1  0
 35 96  1  0
 36 97  1  0
 36 98  1  0
 37 99  1  0
 37100  1  0
 38101  1  0
 38102  1  0
 39103  1  0
 39104  1  0
 40105  1  0
 40106  1  0
 41107  1  0
 41108  1  0
 42109  1  0
 42110  1  0
 43111  1  0
 43112  1  0
 44113  1  0
 44114  1  0
 44115  1  0
M  CHG  2  23  -1  27   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(Dodecanoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-Lauroyl-D-erythro-sphingosylphosphoryl choline	ChEBI
SM(D18:1(4E)/12:0)	ChEBI
Sphingomyelin (D18:1(4E)/12:0)	ChEBI
Sphingomyelin	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-sphing-4-enine	MetBuilder
Sphingomyelin(D18:1/12:0)	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-sphingosine	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphingosine	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-4-sphingenine	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-D-sphingosine	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-sphingenine	MetBuilder
N-(Dodecanoyl)-1-phosphocholine-erythro-4-sphingenine	MetBuilder
C12 Sphingomyelin	HMDB

Chemical Formula

C₃₅H₇₁N₂O₆P

Average Molecular Weight

646.9218

Monoisotopic Molecular Weight

646.504974526

IUPAC Name

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

Traditional Name

(2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]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)CCCCCCCCCCC

InChI Identifier

InChI=1S/C35H71N2O6P/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/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1

InChI Key

HZCLJRFPXMKWHR-FEBLJDHQSA-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

Ceramide phosphocholines (sphingomyelins) (LMSP03010002 )

Ontology

All cells and tissues (HMDB: HMDB0012096)

Cellular substructure

Membrane (HMDB: HMDB0012096)
Endosome (HMDB: HMDB0012096)
Extracellular (HMDB: HMDB0012096)
Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)
Myelin sheath (HMDB: HMDB0012096)
Cell membrane (HMDB: HMDB0012096)
Axon (HMDB: HMDB0012096)

Organelle

Endoplasmic reticulum (PMID: 9009829)

Nervous system (HMDB: HMDB0012096)

Organ

Brain (HMDB: HMDB0012096)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012096)

Source

Endogenous

Endogenous (HMDB: HMDB0012096)

Animal

Animal (HMDB: HMDB0012096)

Exogenous

Food

Food (HMDB: HMDB0012096)

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)

Exogenous (HMDB: HMDB0012096)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012096)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012096)

Lipid metabolism pathway (HMDB: HMDB0012096)

Cellular process

Cell signaling (HMDB: HMDB0012096)
Cell signaling (PMID: 8086039)

Biochemical process

Lipid transport (HMDB: HMDB0012096)

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	4.6e-05 g/L	ALOGPS
logP	4.25	ALOGPS
logP	6.29	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.012	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	195.54 m³·mol⁻¹	ChemAxon
Polarizability	79.96 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]+	259.498	30932474
DeepCCS	[M-H]-	257.673	30932474
DeepCCS	[M-2H]-	290.916	30932474
DeepCCS	[M+Na]+	265.116	30932474
AllCCS	[M+H]+	271.0	32859911
AllCCS	[M+H-H2O]+	270.5	32859911
AllCCS	[M+NH4]+	271.4	32859911
AllCCS	[M+Na]+	271.6	32859911
AllCCS	[M-H]-	262.4	32859911
AllCCS	[M+Na-2H]-	265.9	32859911
AllCCS	[M+HCOO]-	269.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
SM(d18:1/12:0)	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC	4392.6	Standard polar	33892256
SM(d18:1/12:0)	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC	3729.2	Standard non polar	33892256
SM(d18:1/12:0)	CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC	4479.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
SM(d18:1/12:0),1TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC	4267.8	Semi standard non polar	33892256
SM(d18:1/12:0),1TMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C	4298.1	Semi standard non polar	33892256
SM(d18:1/12:0),2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C	4322.4	Semi standard non polar	33892256
SM(d18:1/12:0),2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C	4161.3	Standard non polar	33892256
SM(d18:1/12:0),2TMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C	4875.3	Standard polar	33892256
SM(d18:1/12:0),1TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCC	4582.4	Semi standard non polar	33892256
SM(d18:1/12:0),1TBDMS,isomer #2	CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C(C)(C)C	4533.0	Semi standard non polar	33892256
SM(d18:1/12:0),2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C(C)(C)C	4803.1	Semi standard non polar	33892256
SM(d18:1/12:0),2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C(C)(C)C	4469.6	Standard non polar	33892256
SM(d18:1/12:0),2TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N(C(=O)CCCCCCCCCCC)[Si](C)(C)C(C)(C)C	4835.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d18:1/12:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d18:1/12:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d18:1/12:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d18:1/12:0) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d18:1/12:0) GC-MS ("SM(d18:1/12:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	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 - SM(d18:1/12:0) 10V, Positive-QTOF	splash10-0udi-0000119000-12f4f78497383af17795	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 20V, Positive-QTOF	splash10-0ur0-0000929000-cbbf7f7c9506460209a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 40V, Positive-QTOF	splash10-00di-0000911000-a347a0296da95f64c821	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 10V, Positive-QTOF	splash10-000t-0600009000-9c9626f7c1d63d175cd9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 20V, Positive-QTOF	splash10-000t-0600009000-9c9626f7c1d63d175cd9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 40V, Positive-QTOF	splash10-001i-0900003000-e3fb6ca76868e3afa231	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 10V, Positive-QTOF	splash10-014i-0000109000-74d018f89dc6c564894e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 20V, Positive-QTOF	splash10-0150-0000709000-9694df1aa7fbefb3e9da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 40V, Positive-QTOF	splash10-000i-0000902000-730d818f9723522cedd3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 10V, Negative-QTOF	splash10-0002-0000009000-f1196e26f70d6c4e696c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 20V, Negative-QTOF	splash10-0002-0000029000-bf385d595383fb327983	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d18:1/12:0) 40V, Negative-QTOF	splash10-004i-9103010000-f9506ae49d896ecfc7eb	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028763

KNApSAcK ID

Not Available

Chemspider ID

24846872

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44260123

PDB ID

Not Available

ChEBI ID

17636

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 50 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. 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

4. 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

5. 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

6. 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

7. 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

8. 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

Enzyme Details

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit C

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:: PIGC
Uniprot ID:: Q92535
Molecular weight:: 33582.18

Enzyme Details

10. Ectonucleotide pyrophosphatase/phosphodiesterase family member 7

General function:: Involved in catalytic activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:: ENPP7
Uniprot ID:: Q6UWV6
Molecular weight:: 51493.415

Only showing the first 10 proteins. There are 50 proteins in total.

Show all enzymes and transporters

Showing metabocard for SM(d18:1/12:0) (HMDB0012096)

MOL for HMDB0012096 (SM(d18:1/12:0))

3D MOL for HMDB0012096 (SM(d18:1/12:0))

3D SDF for HMDB0012096 (SM(d18:1/12:0))

3D-SDF for HMDB0012096 (SM(d18:1/12:0))

PDB for HMDB0012096 (SM(d18:1/12:0))

3D PDB for HMDB0012096 (SM(d18:1/12:0))

SMILES for HMDB0012096 (SM(d18:1/12:0))

INCHI for HMDB0012096 (SM(d18:1/12:0))

Structure for HMDB0012096 (SM(d18:1/12:0))

3D Structure for HMDB0012096 (SM(d18:1/12:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes