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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-03-24 16:22:04 UTC

Update Date

2022-11-30 19:04:09 UTC

HMDB ID

HMDB0012082

Secondary Accession Numbers

HMDB12082

Metabolite Identification

Common Name

LysoSM(d18:0)

Description

Sphingomyelin (d18:0/0:0) or LysoSM(d18:0) 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

  Mrv0541 02241203382D          

 31 30  0  0  1  0            999 V2000
   17.8190  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8492   -6.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4992   -6.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -5.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1046  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3900  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6756  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9611  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2466  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5322  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8177  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1032  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3887  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5308  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -7.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598   -7.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164   -8.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1019   -9.2355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1019  -10.0605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1462   -9.0913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -6.3480    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.3874  -10.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8328   -8.1085    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.6578   -9.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598   -8.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5308   -9.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453   -8.8230    0.0000 P   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  1  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  1  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
M  CHG  2  25   1  27  -1
M  END

HMDB0012082
     RDKit          3D
LysoSM(d18:0)
 82 81  0  0  0  0  0  0  0  0999 V2000
   11.5915    0.4541    1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1581   -0.2952   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9130   -1.0675    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7946   -0.1743    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668    0.8348   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3520    1.7319   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0920    0.9623    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528    0.2174   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773   -0.5872   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021    0.3652   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -0.3315   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -1.0377   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381   -1.8325   -1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -1.2886   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -0.7865    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -0.2909    0.7215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0144    0.7315   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6338   -1.4082    0.7234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2590   -2.4959    1.5922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0374   -0.8936    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9813   -0.4681    2.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4064    0.1398    2.9885 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.0932    1.0955    4.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659   -1.1690    3.6783 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.3434    0.9780    1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5841    0.4060    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5032    1.0830    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0472    1.1480   -0.5353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.8273   -0.1416   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115    1.7988   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8742    1.9788   -0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181   -0.2379    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5615    0.9637    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8626    1.2460    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0415    0.4326   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9908   -1.0035   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0860   -1.8375    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5865   -1.6049   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0439    0.3401    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8982   -0.8006    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326    0.3433   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3486    1.4911   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1690    2.4475   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6681    2.3113    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3415    1.7272    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    0.2639    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712    0.8862   -1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.5453   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1260   -1.0140   -1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.3653   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330    1.1460   -1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.8471    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351   -0.8599    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    0.5928   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -1.7560   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -0.3103   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   -2.7150   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045   -2.3824   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.4205   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -1.9891   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -1.5815    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942    0.0631    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048    0.1256    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    1.0522   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -1.8086   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885   -3.0934    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -2.1718    2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -1.8193    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3853   -0.1580    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5546   -0.6721    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0672    0.4543    2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4615    0.4910    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7999    2.1047    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7620   -0.4375   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5374   -0.8952   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9624    0.0045   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9374    1.6917   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1063    1.3814   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1565    2.8853   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8313    2.7248    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9962    1.3067   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9197    2.4982   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  1
 17 64  1  0
 18 65  1  6
 19 66  1  0
 19 67  1  0
 20 68  1  0
 20 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 29 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  0
 31 81  1  0
 31 82  1  0
M  CHG  2  24  -1  28   1
M  END

  Mrv0541 02241203382D          

 31 30  0  0  1  0            999 V2000
   17.8190  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8492   -6.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4992   -6.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -5.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1046  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3900  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6756  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9611  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2466  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5322  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8177  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1032  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3887  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5308  -10.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164  -10.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -7.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598   -7.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8164   -8.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1019   -9.2355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1019  -10.0605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1462   -9.0913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6742   -6.3480    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.3874  -10.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8328   -8.1085    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.6578   -9.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9598   -8.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5308   -9.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453   -8.8230    0.0000 P   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  1  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  1  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
M  CHG  2  25   1  27  -1
M  END
> <DATABASE_ID>
HMDB0012082

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H51N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h22-23,26H,5-21,24H2,1-4H3/t22-,23+/m0/s1

> <INCHI_KEY>
GSEOJHIBPQRSNH-XZOQPEGZSA-N

> <FORMULA>
C23H51N2O5P

> <MOLECULAR_WEIGHT>
466.6352

> <EXACT_MASS>
466.353559264

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
56.39202063239314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
-0.047308685495615635

> <ALOGPS_LOGS>
-5.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.537794180548442

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8298530348162707

> <JCHEM_PKA_STRONGEST_BASIC>
9.732916580907874

> <JCHEM_POLAR_SURFACE_AREA>
104.84

> <JCHEM_REFRACTIVITY>
139.0956

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.04e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012082
     RDKit          3D
LysoSM(d18:0)
 82 81  0  0  0  0  0  0  0  0999 V2000
   11.5915    0.4541    1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1581   -0.2952   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9130   -1.0675    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7946   -0.1743    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668    0.8348   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3520    1.7319   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0920    0.9623    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528    0.2174   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773   -0.5872   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021    0.3652   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -0.3315   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -1.0377   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381   -1.8325   -1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -1.2886   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -0.7865    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -0.2909    0.7215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0144    0.7315   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6338   -1.4082    0.7234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2590   -2.4959    1.5922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0374   -0.8936    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9813   -0.4681    2.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4064    0.1398    2.9885 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.0932    1.0955    4.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659   -1.1690    3.6783 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.3434    0.9780    1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5841    0.4060    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5032    1.0830    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0472    1.1480   -0.5353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.8273   -0.1416   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115    1.7988   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8742    1.9788   -0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181   -0.2379    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5615    0.9637    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8626    1.2460    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0415    0.4326   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9908   -1.0035   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0860   -1.8375    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5865   -1.6049   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0439    0.3401    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8982   -0.8006    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326    0.3433   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3486    1.4911   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1690    2.4475   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6681    2.3113    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3415    1.7272    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    0.2639    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712    0.8862   -1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.5453   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1260   -1.0140   -1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.3653   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330    1.1460   -1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.8471    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351   -0.8599    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    0.5928   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -1.7560   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -0.3103   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   -2.7150   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045   -2.3824   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.4205   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -1.9891   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -1.5815    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942    0.0631    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048    0.1256    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    1.0522   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -1.8086   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885   -3.0934    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -2.1718    2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -1.8193    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3853   -0.1580    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5546   -0.6721    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0672    0.4543    2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4615    0.4910    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7999    2.1047    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7620   -0.4375   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5374   -0.8952   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9624    0.0045   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9374    1.6917   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1063    1.3814   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1565    2.8853   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8313    2.7248    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9962    1.3067   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9197    2.4982   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  1
 17 64  1  0
 18 65  1  6
 19 66  1  0
 19 67  1  0
 20 68  1  0
 20 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 29 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  0
 31 81  1  0
 31 82  1  0
M  CHG  2  24  -1  28   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      33.262 -19.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.385 -11.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.465 -11.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.925 -10.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.929 -18.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.595 -19.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.261 -18.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.927 -19.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.594 -18.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.260 -19.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.926 -18.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.593 -19.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.259 -18.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.925 -19.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.592 -18.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.258 -19.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.924 -18.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.591 -19.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.925 -13.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.592 -14.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.591 -16.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.257 -17.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.257 -18.780   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      11.473 -16.970   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      19.925 -11.850   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0      11.923 -19.550   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      16.488 -15.136   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      18.028 -17.803   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      18.592 -15.700   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      15.924 -17.240   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      17.258 -16.470   0.000  0.00  0.00           P+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                                                            
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                                             
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

COMPND    HMDB0012082
HETATM    1  C1  UNL     1      11.591   0.454   1.069  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.158  -0.295  -0.186  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.913  -1.068   0.089  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.795  -0.174   0.515  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.467   0.835  -0.544  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.352   1.732  -0.123  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.092   0.962   0.164  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.653   0.217  -1.058  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.377  -0.587  -0.847  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.302   0.365  -0.463  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.944  -0.331  -0.206  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.458  -1.038  -1.401  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.238  -1.832  -1.316  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.078  -1.289  -0.938  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.226  -0.786   0.440  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.647  -0.291   0.721  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.014   0.732  -0.112  1.00  0.00           O  
HETATM   18  C17 UNL     1      -3.634  -1.408   0.723  1.00  0.00           C  
HETATM   19  N1  UNL     1      -3.259  -2.496   1.592  1.00  0.00           N  
HETATM   20  C18 UNL     1      -5.037  -0.894   1.072  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.981  -0.468   2.375  1.00  0.00           O  
HETATM   22  P1  UNL     1      -6.406   0.140   2.989  1.00  0.00           P  
HETATM   23  O3  UNL     1      -6.093   1.095   4.143  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.266  -1.169   3.678  1.00  0.00           O1-
HETATM   25  O5  UNL     1      -7.343   0.978   1.891  1.00  0.00           O  
HETATM   26  C19 UNL     1      -8.584   0.406   1.770  1.00  0.00           C  
HETATM   27  C20 UNL     1      -9.503   1.083   0.813  1.00  0.00           C  
HETATM   28  N2  UNL     1      -9.047   1.148  -0.535  1.00  0.00           N1+
HETATM   29  C21 UNL     1      -8.827  -0.142  -1.144  1.00  0.00           C  
HETATM   30  C22 UNL     1     -10.112   1.799  -1.314  1.00  0.00           C  
HETATM   31  C23 UNL     1      -7.874   1.979  -0.677  1.00  0.00           C  
HETATM   32  H1  UNL     1      11.718  -0.238   1.907  1.00  0.00           H  
HETATM   33  H2  UNL     1      12.562   0.964   0.838  1.00  0.00           H  
HETATM   34  H3  UNL     1      10.863   1.246   1.291  1.00  0.00           H  
HETATM   35  H4  UNL     1      11.041   0.433  -0.992  1.00  0.00           H  
HETATM   36  H5  UNL     1      11.991  -1.003  -0.420  1.00  0.00           H  
HETATM   37  H6  UNL     1      10.086  -1.837   0.869  1.00  0.00           H  
HETATM   38  H7  UNL     1       9.587  -1.605  -0.825  1.00  0.00           H  
HETATM   39  H8  UNL     1       9.044   0.340   1.460  1.00  0.00           H  
HETATM   40  H9  UNL     1       7.898  -0.801   0.731  1.00  0.00           H  
HETATM   41  H10 UNL     1       8.233   0.343  -1.515  1.00  0.00           H  
HETATM   42  H11 UNL     1       9.349   1.491  -0.747  1.00  0.00           H  
HETATM   43  H12 UNL     1       7.169   2.447  -0.957  1.00  0.00           H  
HETATM   44  H13 UNL     1       7.668   2.311   0.771  1.00  0.00           H  
HETATM   45  H14 UNL     1       5.342   1.727   0.485  1.00  0.00           H  
HETATM   46  H15 UNL     1       6.224   0.264   1.005  1.00  0.00           H  
HETATM   47  H16 UNL     1       5.471   0.886  -1.920  1.00  0.00           H  
HETATM   48  H17 UNL     1       6.444  -0.545  -1.297  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.126  -1.014  -1.856  1.00  0.00           H  
HETATM   50  H19 UNL     1       4.496  -1.365  -0.090  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.133   1.146  -1.228  1.00  0.00           H  
HETATM   52  H21 UNL     1       3.523   0.847   0.527  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.935  -0.860   0.734  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.281   0.593  -0.081  1.00  0.00           H  
HETATM   55  H24 UNL     1       2.287  -1.756  -1.734  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.397  -0.310  -2.270  1.00  0.00           H  
HETATM   57  H26 UNL     1       0.492  -2.715  -0.597  1.00  0.00           H  
HETATM   58  H27 UNL     1       0.104  -2.382  -2.324  1.00  0.00           H  
HETATM   59  H28 UNL     1      -1.272  -0.421  -1.669  1.00  0.00           H  
HETATM   60  H29 UNL     1      -1.918  -1.989  -1.226  1.00  0.00           H  
HETATM   61  H30 UNL     1      -1.008  -1.582   1.186  1.00  0.00           H  
HETATM   62  H31 UNL     1      -0.594   0.063   0.694  1.00  0.00           H  
HETATM   63  H32 UNL     1      -2.605   0.126   1.764  1.00  0.00           H  
HETATM   64  H33 UNL     1      -2.218   1.052  -0.602  1.00  0.00           H  
HETATM   65  H34 UNL     1      -3.719  -1.809  -0.306  1.00  0.00           H  
HETATM   66  H35 UNL     1      -2.588  -3.093   1.068  1.00  0.00           H  
HETATM   67  H36 UNL     1      -2.787  -2.172   2.465  1.00  0.00           H  
HETATM   68  H37 UNL     1      -5.683  -1.819   1.057  1.00  0.00           H  
HETATM   69  H38 UNL     1      -5.385  -0.158   0.348  1.00  0.00           H  
HETATM   70  H39 UNL     1      -8.555  -0.672   1.513  1.00  0.00           H  
HETATM   71  H40 UNL     1      -9.067   0.454   2.780  1.00  0.00           H  
HETATM   72  H41 UNL     1     -10.461   0.491   0.810  1.00  0.00           H  
HETATM   73  H42 UNL     1      -9.800   2.105   1.127  1.00  0.00           H  
HETATM   74  H43 UNL     1      -7.762  -0.438  -1.009  1.00  0.00           H  
HETATM   75  H44 UNL     1      -9.537  -0.895  -0.784  1.00  0.00           H  
HETATM   76  H45 UNL     1      -8.962   0.004  -2.250  1.00  0.00           H  
HETATM   77  H46 UNL     1      -9.937   1.692  -2.394  1.00  0.00           H  
HETATM   78  H47 UNL     1     -11.106   1.381  -1.063  1.00  0.00           H  
HETATM   79  H48 UNL     1     -10.157   2.885  -1.087  1.00  0.00           H  
HETATM   80  H49 UNL     1      -7.831   2.725   0.143  1.00  0.00           H  
HETATM   81  H50 UNL     1      -6.996   1.307  -0.658  1.00  0.00           H  
HETATM   82  H51 UNL     1      -7.920   2.498  -1.660  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9   47   48
CONECT    9   10   49   50
CONECT   10   11   51   52
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   57   58
CONECT   14   15   59   60
CONECT   15   16   61   62
CONECT   16   17   18   63
CONECT   17   64
CONECT   18   19   20   65
CONECT   19   66   67
CONECT   20   21   68   69
CONECT   21   22
CONECT   22   23   23   24   25
CONECT   25   26
CONECT   26   27   70   71
CONECT   27   28   72   73
CONECT   28   29   30   31
CONECT   29   74   75   76
CONECT   30   77   78   79
CONECT   31   80   81   82
END

HMDB0012082
     RDKit          3D
LysoSM(d18:0)
 82 81  0  0  0  0  0  0  0  0999 V2000
   11.5915    0.4541    1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1581   -0.2952   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9130   -1.0675    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7946   -0.1743    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668    0.8348   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3520    1.7319   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0920    0.9623    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528    0.2174   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773   -0.5872   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021    0.3652   -0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -0.3315   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -1.0377   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381   -1.8325   -1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -1.2886   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -0.7865    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -0.2909    0.7215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0144    0.7315   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6338   -1.4082    0.7234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2590   -2.4959    1.5922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0374   -0.8936    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9813   -0.4681    2.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4064    0.1398    2.9885 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.0932    1.0955    4.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659   -1.1690    3.6783 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.3434    0.9780    1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5841    0.4060    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5032    1.0830    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0472    1.1480   -0.5353 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.8273   -0.1416   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115    1.7988   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8742    1.9788   -0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181   -0.2379    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5615    0.9637    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8626    1.2460    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0415    0.4326   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9908   -1.0035   -0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0860   -1.8375    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5865   -1.6049   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0439    0.3401    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8982   -0.8006    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326    0.3433   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3486    1.4911   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1690    2.4475   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6681    2.3113    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3415    1.7272    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    0.2639    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712    0.8862   -1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.5453   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1260   -1.0140   -1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.3653   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330    1.1460   -1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.8471    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351   -0.8599    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    0.5928   -0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874   -1.7560   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -0.3103   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   -2.7150   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045   -2.3824   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.4205   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -1.9891   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -1.5815    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942    0.0631    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048    0.1256    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    1.0522   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -1.8086   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885   -3.0934    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -2.1718    2.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6826   -1.8193    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3853   -0.1580    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5546   -0.6721    1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0672    0.4543    2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4615    0.4910    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7999    2.1047    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7620   -0.4375   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5374   -0.8952   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9624    0.0045   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9374    1.6917   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1063    1.3814   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1565    2.8853   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8313    2.7248    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9962    1.3067   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9197    2.4982   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  1
 17 64  1  0
 18 65  1  6
 19 66  1  0
 19 67  1  0
 20 68  1  0
 20 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 29 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  0
 31 81  1  0
 31 82  1  0
M  CHG  2  24  -1  28   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dihydrosphingosine-1-phosphocholine	ChEBI
Dihydrosphingosylphosphorylcholine	ChEBI
SM(D18:0/0:0)	ChEBI
Lysosphingomyelin	HMDB
Sphinganine-1-phosphocholine	HMDB
Sphingomyelin(D18:0/0:0)	HMDB
LysoSM(D18:0)	ChEBI

Chemical Formula

C₂₃H₅₁N₂O₅P

Average Molecular Weight

466.6352

Monoisotopic Molecular Weight

466.353559264

IUPAC Name

(2-{[(2S,3R)-2-amino-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-2-amino-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H51N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h22-23,26H,5-21,24H2,1-4H3/t22-,23+/m0/s1

InChI Key

GSEOJHIBPQRSNH-XZOQPEGZSA-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
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Organic zwitterion
Organic salt
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Lysosphingomyelins and lysoglycosphingolipids (LMSP01060002 )

Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0012082)

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012082)

Source

Endogenous

Endogenous (HMDB: HMDB0012082)

Animal

Animal (HMDB: HMDB0012082)

Exogenous

Food

Food (HMDB: HMDB0012082)

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: HMDB0012082)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012082)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012082)

Lipid metabolism pathway (HMDB: HMDB0012082)

Cellular process

Cell signaling (HMDB: HMDB0012082)

Biochemical process

Lipid transport (HMDB: HMDB0012082)

Role

Biological role

Energy source (HMDB: HMDB0012082)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0012082)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012082)

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	0.0007 g/L	ALOGPS
logP	1.72	ALOGPS
logP	-0.047	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.84 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	139.1 m³·mol⁻¹	ChemAxon
Polarizability	56.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	236.443	30932474
DeepCCS	[M-H]-	234.085	30932474
DeepCCS	[M-2H]-	267.223	30932474
DeepCCS	[M+Na]+	243.729	30932474
AllCCS	[M+H]+	230.2	32859911
AllCCS	[M+H-H2O]+	228.6	32859911
AllCCS	[M+NH4]+	231.6	32859911
AllCCS	[M+Na]+	232.0	32859911
AllCCS	[M-H]-	223.5	32859911
AllCCS	[M+Na-2H]-	225.4	32859911
AllCCS	[M+HCOO]-	227.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoSM(d18:0)	CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C	3310.1	Standard polar	33892256
LysoSM(d18:0)	CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C	3056.5	Standard non polar	33892256
LysoSM(d18:0)	CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C	3312.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoSM(d18:0),1TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@@H](N)COP(=O)([O-])OCC[N+](C)(C)C	3187.4	Semi standard non polar	33892256
LysoSM(d18:0),1TMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C	3212.2	Semi standard non polar	33892256
LysoSM(d18:0),2TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C	3216.2	Semi standard non polar	33892256
LysoSM(d18:0),2TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C	3305.0	Standard non polar	33892256
LysoSM(d18:0),2TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C	3751.7	Standard polar	33892256
LysoSM(d18:0),2TMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3411.1	Semi standard non polar	33892256
LysoSM(d18:0),2TMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3391.6	Standard non polar	33892256
LysoSM(d18:0),2TMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3869.5	Standard polar	33892256
LysoSM(d18:0),3TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3435.2	Semi standard non polar	33892256
LysoSM(d18:0),3TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3398.9	Standard non polar	33892256
LysoSM(d18:0),3TMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3585.2	Standard polar	33892256
LysoSM(d18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)COP(=O)([O-])OCC[N+](C)(C)C	3426.7	Semi standard non polar	33892256
LysoSM(d18:0),1TBDMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C(C)(C)C	3463.4	Semi standard non polar	33892256
LysoSM(d18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C(C)(C)C	3676.4	Semi standard non polar	33892256
LysoSM(d18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C(C)(C)C	3656.7	Standard non polar	33892256
LysoSM(d18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N[Si](C)(C)C(C)(C)C	3782.5	Standard polar	33892256
LysoSM(d18:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3871.5	Semi standard non polar	33892256
LysoSM(d18:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3682.3	Standard non polar	33892256
LysoSM(d18:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3852.0	Standard polar	33892256
LysoSM(d18:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4110.9	Semi standard non polar	33892256
LysoSM(d18:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3859.2	Standard non polar	33892256
LysoSM(d18:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3652.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoSM(d18:0) GC-MS (1 TMS) - 70eV, Positive	splash10-006t-7491010000-bc23518378651a125026	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoSM(d18:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoSM(d18:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - LysoSM(d18:0) 10V, Positive-QTOF	splash10-014i-1000900000-35836a2c431e77f6873a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoSM(d18:0) 20V, Positive-QTOF	splash10-001i-5900400000-a5032e7b8458e4cccdfb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoSM(d18:0) 40V, Positive-QTOF	splash10-00ei-7900000000-d73159bd733c71cdc9ca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoSM(d18:0) 10V, Negative-QTOF	splash10-014i-0000900000-bb2c6f0eea52c6f216cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoSM(d18:0) 20V, Negative-QTOF	splash10-014i-0001900000-1f2da57e5c3981a4dd85	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoSM(d18:0) 40V, Negative-QTOF	splash10-004i-9202000000-a26f998ebee8f775788f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB028751

KNApSAcK ID

Not Available

Chemspider ID

21403135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44260122

PDB ID

Not Available

ChEBI ID

132478

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 ]
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.

Enzymes

Enzyme Details

1. 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

2. 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

3. 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

Enzyme Details

4. Sphingomyelin phosphodiesterase 2

General function:: Involved in metal ion binding
Specific function:: Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:: SMPD2
Uniprot ID:: O60906
Molecular weight:: 47645.29

Enzyme Details

5. Proactivator polypeptide

General function:: Involved in lipid metabolic process
Specific function:: Saposin-D is a specific sphingomyelin phosphodiesterase activator (EC 3.1.4.12)
Gene Name:: PSAP
Uniprot ID:: P07602
Molecular weight:: 58112.1

Enzyme Details

6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3

General function:: Involved in calcium ion binding
Specific function:: Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Essential for trophoblast and placental development. May participate in cytokinesis by hydrolyzing PIP2 at the cleavage furrow.
Gene Name:: PLCD3
Uniprot ID:: Q8N3E9
Molecular weight:: 89257.54

Enzyme Details

7. Sphingomyelin phosphodiesterase 3

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:: SMPD3
Uniprot ID:: Q9NY59
Molecular weight:: 71080.1

Enzyme Details

8. Sphingomyelin phosphodiesterase 4

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:: SMPD4
Uniprot ID:: Q9NXE4
Molecular weight:: 86192.575

Enzyme Details

9. Non-lysosomal glucosylceramidase

General function:: Involved in catalytic activity
Specific function:: Non-lysosomal glucosylceramidase that catalyzes the conversion of glucosylceramide to free glucose and ceramide. Involved in sphingomyelin generation and prevention of glycolipid accumulation. May also catalyze the hydrolysis of bile acid 3-O-glucosides, however, the relevance of such activity is unclear in vivo.
Gene Name:: GBA2
Uniprot ID:: Q9HCG7
Molecular weight:: 104648.13

Enzyme Details

10. Sphingomyelin synthase-related protein 1

General function:: Involved in sphingomyelin biosynthetic process
Specific function:: Not Available
Gene Name:: SAMD8
Uniprot ID:: Q96LT4
Molecular weight:: 48320.2

Showing metabocard for LysoSM(d18:0) (HMDB0012082)

MOL for HMDB0012082 (LysoSM(d18:0))

3D MOL for HMDB0012082 (LysoSM(d18:0))

3D SDF for HMDB0012082 (LysoSM(d18:0))

3D-SDF for HMDB0012082 (LysoSM(d18:0))

PDB for HMDB0012082 (LysoSM(d18:0))

3D PDB for HMDB0012082 (LysoSM(d18:0))

SMILES for HMDB0012082 (LysoSM(d18:0))

INCHI for HMDB0012082 (LysoSM(d18:0))

Structure for HMDB0012082 (LysoSM(d18:0))

3D Structure for HMDB0012082 (LysoSM(d18:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes