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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-12-18 22:44:58 UTC

Update Date

2022-11-30 19:53:42 UTC

HMDB ID

HMDB0240621

Secondary Accession Numbers

None

Metabolite Identification

Common Name

SM(d17:1/22:0)

Description

Sphingomyelin (d17:1/22:0) or SM(d17:1/22:0) 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. SM(d17:1/22:0) consists of a heptadecasphingosine backbone and a behenic acid chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM 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 localize 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

SM(d17:1/22:0)
  Mrv1652312181923412D          

 54 53  0  0  0  0            999 V2000
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    1.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0574    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2748    1.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0969    1.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5251    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9534    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6675    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3816    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0957    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8099    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5240    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2381    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9522    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6663    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3805    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0946    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7942   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5083   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3648   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0789   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7931   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5072   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2213   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9354   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6496   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3637   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0778   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7919   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.5060   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  6  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9  6  1  0  0  0  0
  5  2  1  0  0  0  0
  1 16  1  0  0  0  0
  4 32  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  CHG  2   8  -1  12   1
M  END

HMDB0240621
     RDKit          3D
SM(d17:1/22:0)
142141  0  0  0  0  0  0  0  0999 V2000
    1.0805   -1.3903   -3.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460   -0.7128   -5.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    0.1380   -5.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884   -0.6557   -4.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    0.2610   -4.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   -0.3031   -4.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7151   -0.9695   -2.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012   -2.2106   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -3.3175   -3.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869   -4.6135   -3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1086   -4.5694   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -5.9531   -2.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1255   -5.8811   -2.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4517   -4.7464   -2.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -4.6706   -2.1736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4516   -5.9217   -1.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -3.5913   -1.1721 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2889   -3.9303    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -4.0188    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3908   -4.3837    1.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.8768   -4.0407    1.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -6.0377    1.8597 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7908   -3.4671    2.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008   -3.8164    3.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0403   -3.0441    5.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532   -3.2521    5.5071 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.3596   -2.3774    6.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4269   -4.5973    5.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -2.8516    4.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -3.5046   -1.0050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5162   -2.3348   -1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -1.3363   -1.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667   -2.1767   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5113   -0.8284   -1.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    0.2752   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5246    1.6451   -0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9838    1.8132   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3652    3.2622   -1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1570    3.6053   -2.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4090    5.0169   -2.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590    6.0579   -2.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318    6.2165   -1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    7.3707   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7536    7.8085    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    6.8168    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0310    5.7969    1.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    4.7570    2.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    5.3697    3.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    4.2684    4.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    3.4398    3.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791    4.2151    3.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646    4.8463    4.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    3.6812    5.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517   -2.4406   -4.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -0.8568   -3.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -1.3580   -3.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.4853   -5.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076   -0.0891   -5.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9329    0.6303   -6.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5643    0.9524   -4.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781   -1.4067   -5.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7174   -1.2006   -3.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    1.1583   -3.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2744    0.7712   -5.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2872    0.5058   -4.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -1.0025   -5.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5896   -0.1723   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8371   -1.2119   -2.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9921   -2.1357   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5864   -2.6123   -1.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3096   -3.5212   -3.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595   -2.9369   -4.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1252   -5.0259   -2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8601   -5.3403   -3.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -3.9357   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347   -4.1657   -3.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -6.6103   -3.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519   -6.3625   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245   -6.8299   -2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011   -3.8522   -2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744   -4.4416   -3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2279   -6.2510   -2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580   -2.6209   -1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0866   -4.9758    0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0659   -3.2735    0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622   -3.5273    3.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809   -4.9015    4.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609   -1.9805    5.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6207   -3.4523    6.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -1.4030    6.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.8481    7.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206   -2.1760    6.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469   -4.5840    6.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -5.3377    5.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3281   -4.8670    6.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -3.6208    3.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887   -1.8777    4.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -2.6790    4.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167   -4.3412   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2115   -2.4968   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4725   -2.9714   -1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6289   -0.8859   -1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8795    0.3593   -0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265    1.9937   -1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241    2.3405   -0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9309    3.9140   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4366    5.3392   -2.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0366    6.2862   -0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715    5.2964   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2586    7.0584   -1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0372    8.6849    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6910    8.2051    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445    7.3535    2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056    6.2924    0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6722    6.3700    2.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567    5.3704    1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6342    4.1878    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0221    4.0291    3.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    6.0738    3.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    5.9383    4.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697    3.5822    5.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831    4.6659    5.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8204    3.4664    2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9383    5.3134    3.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    5.5194    5.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8411    3.3216    5.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4807    4.0007    5.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    2.8973    4.4470 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
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 13 14  2  0
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 14 80  1  0
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 38110  1  0
 38111  1  0
 39112  1  0
 39113  1  0
 40114  1  0
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 51136  1  0
 51137  1  0
 52138  1  0
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 53140  1  0
 53141  1  0
 53142  1  0
M  CHG  2  22  -1  26   1
M  END

SM(d17:1/22:0)
  Mrv1652312181923412D          

 54 53  0  0  0  0            999 V2000
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    1.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0574    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2748    1.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0969    1.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9534    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6675    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3816    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0957    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8099    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5240    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2381    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9522    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6663    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.0946    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2225   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6507   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -18.5060   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  6  0  0  0
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  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9  6  1  0  0  0  0
  5  2  1  0  0  0  0
  1 16  1  0  0  0  0
  4 32  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  CHG  2   8  -1  12   1
M  END
> <DATABASE_ID>
HMDB0240621

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H89N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-28-30-32-34-36-38-44(48)45-42(41-52-53(49,50)51-40-39-46(3,4)5)43(47)37-35-33-31-29-27-19-17-15-13-11-9-7-2/h35,37,42-43,47H,6-34,36,38-41H2,1-5H3,(H-,45,48,49,50)/b37-35+/t42-,43+/m0/s1

> <INCHI_KEY>
BEHLQMQPYDCEFC-QVDCKBILSA-N

> <FORMULA>
C44H89N2O6P

> <MOLECULAR_WEIGHT>
773.178

> <EXACT_MASS>
772.645825592

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
142

> <JCHEM_AVERAGE_POLARIZABILITY>
99.57828572834833

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.93

> <JCHEM_LOGP>
9.198901065861593

> <ALOGPS_LOGS>
-7.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.49920132064026

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.865155035270682

> <JCHEM_PKA_STRONGEST_BASIC>
-1.050204146041731

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
236.94690000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.60e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240621
     RDKit          3D
SM(d17:1/22:0)
142141  0  0  0  0  0  0  0  0999 V2000
    1.0805   -1.3903   -3.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460   -0.7128   -5.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    0.1380   -5.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884   -0.6557   -4.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    0.2610   -4.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   -0.3031   -4.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7151   -0.9695   -2.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012   -2.2106   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -3.3175   -3.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869   -4.6135   -3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1086   -4.5694   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -5.9531   -2.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4517   -4.7464   -2.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2889   -3.9303    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -4.0188    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  22  -1  26   1
M  END

HEADER    PROTEIN                                 18-DEC-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: SM(d17:1/22:0)                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-DEC-19         0                                  
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HETATM   40  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -17.215  -1.433   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -19.881  -1.433   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -22.547  -1.433   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -23.880  -0.662   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -25.213  -1.433   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -26.546  -0.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -27.879  -1.433   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -29.213  -0.662   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -30.546  -1.433   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -31.879  -0.662   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -33.212  -1.433   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -34.545  -0.662   0.000  0.00  0.00           C+0
CONECT    1    2    3    4   16                                             
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1   32                                                       
CONECT    5    6    2                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10    6                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    1   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    4   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  106    0
END

COMPND    HMDB0240621
HETATM    1  C1  UNL     1       1.080  -1.390  -3.958  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.546  -0.713  -5.197  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.754   0.138  -5.077  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.988  -0.656  -4.631  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.159   0.261  -4.521  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.470  -0.303  -4.160  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.715  -0.970  -2.883  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.001  -2.211  -2.510  1.00  0.00           C  
HETATM    9  C9  UNL     1       6.214  -3.318  -3.525  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.587  -4.613  -3.161  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.109  -4.569  -2.944  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.589  -5.953  -2.584  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.125  -5.881  -2.335  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.452  -4.746  -2.421  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.008  -4.671  -2.174  1.00  0.00           C  
HETATM   16  O1  UNL     1      -0.452  -5.922  -1.779  1.00  0.00           O  
HETATM   17  C16 UNL     1      -0.349  -3.591  -1.172  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.289  -3.930   0.171  1.00  0.00           C  
HETATM   19  O2  UNL     1       1.656  -4.019   0.096  1.00  0.00           O  
HETATM   20  P1  UNL     1       2.391  -4.384   1.546  1.00  0.00           P  
HETATM   21  O3  UNL     1       3.877  -4.041   1.388  1.00  0.00           O  
HETATM   22  O4  UNL     1       2.331  -6.038   1.860  1.00  0.00           O1-
HETATM   23  O5  UNL     1       1.791  -3.467   2.834  1.00  0.00           O  
HETATM   24  C18 UNL     1       2.501  -3.816   3.975  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.040  -3.044   5.191  1.00  0.00           C  
HETATM   26  N1  UNL     1       0.653  -3.252   5.507  1.00  0.00           N1+
HETATM   27  C20 UNL     1       0.360  -2.377   6.656  1.00  0.00           C  
HETATM   28  C21 UNL     1       0.427  -4.597   5.973  1.00  0.00           C  
HETATM   29  C22 UNL     1      -0.245  -2.852   4.451  1.00  0.00           C  
HETATM   30  N2  UNL     1      -1.791  -3.505  -1.005  1.00  0.00           N  
HETATM   31  C23 UNL     1      -2.516  -2.335  -1.288  1.00  0.00           C  
HETATM   32  O6  UNL     1      -1.840  -1.336  -1.714  1.00  0.00           O  
HETATM   33  C24 UNL     1      -3.967  -2.177  -1.131  1.00  0.00           C  
HETATM   34  C25 UNL     1      -4.511  -0.828  -1.447  1.00  0.00           C  
HETATM   35  C26 UNL     1      -3.974   0.275  -0.624  1.00  0.00           C  
HETATM   36  C27 UNL     1      -4.525   1.645  -0.949  1.00  0.00           C  
HETATM   37  C28 UNL     1      -5.984   1.813  -0.755  1.00  0.00           C  
HETATM   38  C29 UNL     1      -6.365   3.262  -1.120  1.00  0.00           C  
HETATM   39  C30 UNL     1      -6.157   3.605  -2.529  1.00  0.00           C  
HETATM   40  C31 UNL     1      -6.409   5.017  -2.889  1.00  0.00           C  
HETATM   41  C32 UNL     1      -5.459   6.058  -2.467  1.00  0.00           C  
HETATM   42  C33 UNL     1      -5.132   6.217  -1.009  1.00  0.00           C  
HETATM   43  C34 UNL     1      -4.193   7.371  -0.886  1.00  0.00           C  
HETATM   44  C35 UNL     1      -3.754   7.809   0.452  1.00  0.00           C  
HETATM   45  C36 UNL     1      -3.130   6.817   1.365  1.00  0.00           C  
HETATM   46  C37 UNL     1      -4.031   5.797   1.959  1.00  0.00           C  
HETATM   47  C38 UNL     1      -3.298   4.757   2.806  1.00  0.00           C  
HETATM   48  C39 UNL     1      -2.537   5.370   3.935  1.00  0.00           C  
HETATM   49  C40 UNL     1      -1.881   4.268   4.729  1.00  0.00           C  
HETATM   50  C41 UNL     1      -0.949   3.440   3.890  1.00  0.00           C  
HETATM   51  C42 UNL     1       0.179   4.215   3.275  1.00  0.00           C  
HETATM   52  C43 UNL     1       1.065   4.846   4.349  1.00  0.00           C  
HETATM   53  C44 UNL     1       1.612   3.681   5.179  1.00  0.00           C  
HETATM   54  H1  UNL     1       0.752  -2.441  -4.083  1.00  0.00           H  
HETATM   55  H2  UNL     1       0.148  -0.857  -3.600  1.00  0.00           H  
HETATM   56  H3  UNL     1       1.807  -1.358  -3.121  1.00  0.00           H  
HETATM   57  H4  UNL     1       1.761  -1.485  -5.973  1.00  0.00           H  
HETATM   58  H5  UNL     1       0.708  -0.089  -5.614  1.00  0.00           H  
HETATM   59  H6  UNL     1       2.933   0.630  -6.055  1.00  0.00           H  
HETATM   60  H7  UNL     1       2.564   0.952  -4.332  1.00  0.00           H  
HETATM   61  H8  UNL     1       4.178  -1.407  -5.414  1.00  0.00           H  
HETATM   62  H9  UNL     1       3.717  -1.201  -3.724  1.00  0.00           H  
HETATM   63  H10 UNL     1       4.889   1.158  -3.870  1.00  0.00           H  
HETATM   64  H11 UNL     1       5.274   0.771  -5.541  1.00  0.00           H  
HETATM   65  H12 UNL     1       7.287   0.506  -4.330  1.00  0.00           H  
HETATM   66  H13 UNL     1       6.742  -1.003  -5.043  1.00  0.00           H  
HETATM   67  H14 UNL     1       6.590  -0.172  -2.072  1.00  0.00           H  
HETATM   68  H15 UNL     1       7.837  -1.212  -2.800  1.00  0.00           H  
HETATM   69  H16 UNL     1       4.992  -2.136  -2.126  1.00  0.00           H  
HETATM   70  H17 UNL     1       6.586  -2.612  -1.590  1.00  0.00           H  
HETATM   71  H18 UNL     1       7.310  -3.521  -3.662  1.00  0.00           H  
HETATM   72  H19 UNL     1       5.860  -2.937  -4.511  1.00  0.00           H  
HETATM   73  H20 UNL     1       6.125  -5.026  -2.259  1.00  0.00           H  
HETATM   74  H21 UNL     1       5.860  -5.340  -3.982  1.00  0.00           H  
HETATM   75  H22 UNL     1       3.928  -3.936  -2.036  1.00  0.00           H  
HETATM   76  H23 UNL     1       3.635  -4.166  -3.846  1.00  0.00           H  
HETATM   77  H24 UNL     1       3.732  -6.610  -3.484  1.00  0.00           H  
HETATM   78  H25 UNL     1       4.152  -6.363  -1.738  1.00  0.00           H  
HETATM   79  H26 UNL     1       1.625  -6.830  -2.070  1.00  0.00           H  
HETATM   80  H27 UNL     1       2.001  -3.852  -2.677  1.00  0.00           H  
HETATM   81  H28 UNL     1      -0.574  -4.442  -3.127  1.00  0.00           H  
HETATM   82  H29 UNL     1      -1.228  -6.251  -2.281  1.00  0.00           H  
HETATM   83  H30 UNL     1       0.058  -2.621  -1.496  1.00  0.00           H  
HETATM   84  H31 UNL     1      -0.087  -4.976   0.387  1.00  0.00           H  
HETATM   85  H32 UNL     1      -0.066  -3.273   0.972  1.00  0.00           H  
HETATM   86  H33 UNL     1       3.562  -3.527   3.800  1.00  0.00           H  
HETATM   87  H34 UNL     1       2.481  -4.901   4.179  1.00  0.00           H  
HETATM   88  H35 UNL     1       2.261  -1.980   5.123  1.00  0.00           H  
HETATM   89  H36 UNL     1       2.621  -3.452   6.060  1.00  0.00           H  
HETATM   90  H37 UNL     1       0.873  -1.403   6.482  1.00  0.00           H  
HETATM   91  H38 UNL     1       0.744  -2.848   7.589  1.00  0.00           H  
HETATM   92  H39 UNL     1      -0.721  -2.176   6.687  1.00  0.00           H  
HETATM   93  H40 UNL     1      -0.447  -4.584   6.641  1.00  0.00           H  
HETATM   94  H41 UNL     1       0.333  -5.338   5.155  1.00  0.00           H  
HETATM   95  H42 UNL     1       1.328  -4.867   6.593  1.00  0.00           H  
HETATM   96  H43 UNL     1      -0.381  -3.621   3.684  1.00  0.00           H  
HETATM   97  H44 UNL     1       0.089  -1.878   4.061  1.00  0.00           H  
HETATM   98  H45 UNL     1      -1.246  -2.679   4.909  1.00  0.00           H  
HETATM   99  H46 UNL     1      -2.317  -4.341  -0.659  1.00  0.00           H  
HETATM  100  H47 UNL     1      -4.212  -2.497  -0.078  1.00  0.00           H  
HETATM  101  H48 UNL     1      -4.473  -2.971  -1.757  1.00  0.00           H  
HETATM  102  H49 UNL     1      -5.629  -0.886  -1.281  1.00  0.00           H  
HETATM  103  H50 UNL     1      -4.394  -0.677  -2.543  1.00  0.00           H  
HETATM  104  H51 UNL     1      -4.146   0.012   0.451  1.00  0.00           H  
HETATM  105  H52 UNL     1      -2.879   0.359  -0.733  1.00  0.00           H  
HETATM  106  H53 UNL     1      -4.126   1.994  -1.920  1.00  0.00           H  
HETATM  107  H54 UNL     1      -4.024   2.341  -0.202  1.00  0.00           H  
HETATM  108  H55 UNL     1      -6.615   1.114  -1.325  1.00  0.00           H  
HETATM  109  H56 UNL     1      -6.299   1.714   0.306  1.00  0.00           H  
HETATM  110  H57 UNL     1      -5.931   3.914  -0.390  1.00  0.00           H  
HETATM  111  H58 UNL     1      -7.496   3.356  -0.932  1.00  0.00           H  
HETATM  112  H59 UNL     1      -5.146   3.259  -2.897  1.00  0.00           H  
HETATM  113  H60 UNL     1      -6.885   2.966  -3.146  1.00  0.00           H  
HETATM  114  H61 UNL     1      -6.476   5.103  -4.030  1.00  0.00           H  
HETATM  115  H62 UNL     1      -7.437   5.339  -2.556  1.00  0.00           H  
HETATM  116  H63 UNL     1      -5.855   7.070  -2.809  1.00  0.00           H  
HETATM  117  H64 UNL     1      -4.466   5.988  -3.015  1.00  0.00           H  
HETATM  118  H65 UNL     1      -6.037   6.286  -0.427  1.00  0.00           H  
HETATM  119  H66 UNL     1      -4.472   5.296  -0.758  1.00  0.00           H  
HETATM  120  H67 UNL     1      -4.613   8.233  -1.479  1.00  0.00           H  
HETATM  121  H68 UNL     1      -3.259   7.058  -1.460  1.00  0.00           H  
HETATM  122  H69 UNL     1      -3.037   8.685   0.378  1.00  0.00           H  
HETATM  123  H70 UNL     1      -4.691   8.205   0.977  1.00  0.00           H  
HETATM  124  H71 UNL     1      -2.544   7.354   2.184  1.00  0.00           H  
HETATM  125  H72 UNL     1      -2.306   6.292   0.793  1.00  0.00           H  
HETATM  126  H73 UNL     1      -4.672   6.370   2.739  1.00  0.00           H  
HETATM  127  H74 UNL     1      -4.757   5.370   1.307  1.00  0.00           H  
HETATM  128  H75 UNL     1      -2.634   4.188   2.103  1.00  0.00           H  
HETATM  129  H76 UNL     1      -4.022   4.029   3.195  1.00  0.00           H  
HETATM  130  H77 UNL     1      -1.733   6.074   3.562  1.00  0.00           H  
HETATM  131  H78 UNL     1      -3.173   5.938   4.623  1.00  0.00           H  
HETATM  132  H79 UNL     1      -2.670   3.582   5.105  1.00  0.00           H  
HETATM  133  H80 UNL     1      -1.283   4.666   5.588  1.00  0.00           H  
HETATM  134  H81 UNL     1      -1.506   2.896   3.100  1.00  0.00           H  
HETATM  135  H82 UNL     1      -0.556   2.634   4.581  1.00  0.00           H  
HETATM  136  H83 UNL     1       0.820   3.466   2.736  1.00  0.00           H  
HETATM  137  H84 UNL     1      -0.191   4.938   2.548  1.00  0.00           H  
HETATM  138  H85 UNL     1       1.938   5.313   3.858  1.00  0.00           H  
HETATM  139  H86 UNL     1       0.504   5.519   5.002  1.00  0.00           H  
HETATM  140  H87 UNL     1       0.841   3.322   5.878  1.00  0.00           H  
HETATM  141  H88 UNL     1       2.481   4.001   5.790  1.00  0.00           H  
HETATM  142  H89 UNL     1       1.914   2.897   4.447  1.00  0.00           H  
CONECT    1    2   54   55   56
CONECT    2    3   57   58
CONECT    3    4   59   60
CONECT    4    5   61   62
CONECT    5    6   63   64
CONECT    6    7   65   66
CONECT    7    8   67   68
CONECT    8    9   69   70
CONECT    9   10   71   72
CONECT   10   11   73   74
CONECT   11   12   75   76
CONECT   12   13   77   78
CONECT   13   14   14   79
CONECT   14   15   80
CONECT   15   16   17   81
CONECT   16   82
CONECT   17   18   30   83
CONECT   18   19   84   85
CONECT   19   20
CONECT   20   21   21   22   23
CONECT   23   24
CONECT   24   25   86   87
CONECT   25   26   88   89
CONECT   26   27   28   29
CONECT   27   90   91   92
CONECT   28   93   94   95
CONECT   29   96   97   98
CONECT   30   31   99
CONECT   31   32   32   33
CONECT   33   34  100  101
CONECT   34   35  102  103
CONECT   35   36  104  105
CONECT   36   37  106  107
CONECT   37   38  108  109
CONECT   38   39  110  111
CONECT   39   40  112  113
CONECT   40   41  114  115
CONECT   41   42  116  117
CONECT   42   43  118  119
CONECT   43   44  120  121
CONECT   44   45  122  123
CONECT   45   46  124  125
CONECT   46   47  126  127
CONECT   47   48  128  129
CONECT   48   49  130  131
CONECT   49   50  132  133
CONECT   50   51  134  135
CONECT   51   52  136  137
CONECT   52   53  138  139
CONECT   53  140  141  142
END

HMDB0240621
     RDKit          3D
SM(d17:1/22:0)
142141  0  0  0  0  0  0  0  0999 V2000
    1.0805   -1.3903   -3.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460   -0.7128   -5.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    0.1380   -5.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884   -0.6557   -4.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589    0.2610   -4.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   -0.3031   -4.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7151   -0.9695   -2.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012   -2.2106   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -3.3175   -3.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869   -4.6135   -3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1086   -4.5694   -2.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  22  -1  26   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(Docosanoyl)heptadecasphing-4-enine-1-phosphocholine	ChEBI
Sphingomyelin D17:1/22:0	ChEBI
SM D17:1/22:0	HMDB
Sphingomyelin (D17:1,C22:0)	HMDB
Sphingomyelin (D17:1/22:0)	HMDB
SM(D17:1/22:0)	ChEBI

Chemical Formula

C₄₄H₈₉N₂O₆P

Average Molecular Weight

773.178

Monoisotopic Molecular Weight

772.645825592

IUPAC Name

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

Traditional Name

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

CAS Registry Number

121999-70-0

SMILES

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

InChI Identifier

InChI=1S/C44H89N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-28-30-32-34-36-38-44(48)45-42(41-52-53(49,50)51-40-39-46(3,4)5)43(47)37-35-33-31-29-27-19-17-15-13-11-9-7-2/h35,37,42-43,47H,6-34,36,38-41H2,1-5H3,(H-,45,48,49,50)/b37-35+/t42-,43+/m0/s1

InChI Key

BEHLQMQPYDCEFC-QVDCKBILSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Phosphocholines

Alternative Parents

Substituents

Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Amine
Alcohol
Organic oxide
Organic zwitterion
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Ceramide phosphocholines (sphingomyelins) (LMSP03010066 )

Ontology

All cells and tissues (HMDB: HMDB0240621)

Organ

Placenta (HMDB: HMDB0240621)

Cellular substructure

Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)

Organelle

Endoplasmic reticulum (PMID: 9009829)

Source

Endogenous

Endogenous (HMDB: HMDB0240621)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (PMID: 8086039)

Role

Biological role

Nutrient (PMID: 23684760)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

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
logP	5.93	ALOGPS
logP	9.2	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	236.95 m³·mol⁻¹	ChemAxon
Polarizability	99.58 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]+	288.599	30932474
DeepCCS	[M-H]-	286.203	30932474
DeepCCS	[M-2H]-	319.299	30932474
DeepCCS	[M+Na]+	294.513	30932474
AllCCS	[M+H]+	295.9	32859911
AllCCS	[M+H-H2O]+	295.7	32859911
AllCCS	[M+NH4]+	296.1	32859911
AllCCS	[M+Na]+	296.1	32859911
AllCCS	[M-H]-	289.5	32859911
AllCCS	[M+Na-2H]-	293.0	32859911
AllCCS	[M+HCOO]-	297.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.64 minutes	32390414
Predicted by Siyang on May 30, 2022	35.6206 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5355.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	397.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	400.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1092.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1746.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1386.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	581.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3959.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1093.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	3389.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1147.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	781.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	346.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	300.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
SM(d17:1/22:0)	[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCC	4901.5	Standard polar	33892256
SM(d17:1/22:0)	[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCC	4208.6	Standard non polar	33892256
SM(d17:1/22:0)	[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCC	5448.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d17:1/22:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d17:1/22:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d17:1/22:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - SM(d17:1/22:0) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 10V, Negative-QTOF	splash10-00di-0000000900-9d42de707cae3a9b8a32	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 20V, Negative-QTOF	splash10-00di-1000002900-8db13bc596fb82162c34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 40V, Negative-QTOF	splash10-004i-9100000000-d3b527eab5162b1ebc8d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 10V, Positive-QTOF	splash10-004i-0000010900-bdb9951f461c189ac712	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 20V, Positive-QTOF	splash10-004k-0000070900-e739e77c3dbbdec222a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 40V, Positive-QTOF	splash10-0002-0000090200-3a7b1abe1098405c60ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 10V, Positive-QTOF	splash10-00e9-0600000900-36ca86b57ac3fc62c072	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 20V, Positive-QTOF	splash10-00e9-0600000900-36ca86b57ac3fc62c072	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 40V, Positive-QTOF	splash10-001i-0900000300-c78f800388b7ae592942	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 10V, Positive-QTOF	splash10-0002-0000001900-7c336888ff915efafbd1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 20V, Positive-QTOF	splash10-03dk-0000007900-563ab8be8835f4f62ef2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - SM(d17:1/22:0) 40V, Positive-QTOF	splash10-03di-0000039300-ba7fd1d8151e3487bb2b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Placenta

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64808543

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52931191

PDB ID

Not Available

ChEBI ID

136275

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

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for SM(d17:1/22:0) (HMDB0240621)

MOL for HMDB0240621 (SM(d17:1/22:0))

3D MOL for HMDB0240621 (SM(d17:1/22:0))

3D SDF for HMDB0240621 (SM(d17:1/22:0))

3D-SDF for HMDB0240621 (SM(d17:1/22:0))

PDB for HMDB0240621 (SM(d17:1/22:0))

3D PDB for HMDB0240621 (SM(d17:1/22:0))

SMILES for HMDB0240621 (SM(d17:1/22:0))

INCHI for HMDB0240621 (SM(d17:1/22:0))

Structure for HMDB0240621 (SM(d17:1/22:0))

3D Structure for HMDB0240621 (SM(d17:1/22:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra