NP-MRD: Showing NP-Card for SM(d18:0/18:1(11Z)) (NP0091902)

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Record Information

Version

2.0

Created at

2022-05-11 18:51:33 UTC

Updated at

2022-05-11 18:51:33 UTC

NP-MRD ID

NP0091902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

SM(d18:0/18:1(11Z))

Description

SM(d18:0/18:1(11Z)) is a sphingomyelin (SM). Sphingomyelins are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.G. Sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). SM is the major sphingolipid in mammals it is found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. SM contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme sphingomyelinase, which causes the accumulation of sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. In terms of its appearance and structure, SM(d18:0/18:1(11Z)) consists of a saturated 18-carbon sphingoid base with an attached unsaturated 11Z-octadecenoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02251206132D          

 52 51  0  0  1  0            999 V2000
   15.3730    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8020    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5164    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2309    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9454    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6599    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3743    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0888    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8033    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2322    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9467    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6612    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3756    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0901    9.2881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.0901    8.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8046    9.7006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8046   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190   10.9381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190   11.7631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.6940   11.7631    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   28.3440   11.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190   12.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335   13.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9480   14.2381    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   29.3605   13.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5355   14.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6624   14.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5190    9.2881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2335   10.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9480    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6624    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3769    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8059    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5203    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2348    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9493    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6637    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3782    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0927    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072    9.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8072   10.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5216   11.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2361   12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2361   13.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3756    8.8756    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.5191   10.1131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  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  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  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
 21 23  2  0  0  0  0
 21 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
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 18 31  1  6  0  0  0
 31 32  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
 43 42  1  4  0  0  0
 43 44  2  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
 16 51  1  1  0  0  0
 18 52  1  1  0  0  0
M  CHG  2  22  -1  27   1
M  END

     RDKit          3D

133132  0  0  0  0  0  0  0  0999 V2000
   -5.5213    6.0863   -1.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945    5.2180   -1.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    5.8352   -2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1291    5.0067   -2.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    4.6031   -1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    5.5676   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    6.4549    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214    6.5465    1.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638    5.7978    2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577    5.0314    3.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    4.0087    2.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141    2.7915    2.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0263    1.7696    3.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    2.0125    3.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    2.3052    2.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552    1.1943    1.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -0.0807    2.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780   -1.1538    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3249   -0.8890    0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698   -2.3960    1.9830 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -3.5087    1.1465 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9131   -3.3411    1.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0458   -2.0897    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873   -1.5879    0.0963 P   0  0  2  0  0  5  0  0  0  0  0  0
    7.6035   -2.5570    0.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9272   -0.0670    0.8084 O   0  0  0  0  0  1  0  0  0  0  0  0
    6.8502   -1.4175   -1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6432   -1.6529   -2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7525   -1.5242   -3.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.7807   -4.3471 N   0  0  1  0  0  4  0  0  0  0  0  0
    3.4123   -1.1753   -3.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680   -1.2150   -5.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919   -3.2152   -4.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -4.8520    1.6766 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6783   -5.7819    0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044   -5.2627    1.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -4.5096    2.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5940   -5.1344    2.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -5.3372    1.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -4.1673    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465   -3.1674    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -2.0339    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.9636    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8978   -1.1019    1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9938   -1.5471    0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821   -2.8832   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2313   -3.5070   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9847   -2.6752   -2.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063   -3.3544   -3.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7698   -2.5084   -4.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5051    7.0039   -1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4151    5.5132   -1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6202    6.3094   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    4.2163   -1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776    5.0312   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    6.8737   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9420    5.8397   -3.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5348    5.5066   -3.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4591    4.0465   -3.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    3.9186   -0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    3.8816   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332    5.0207    0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    6.1848   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    7.1213   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    7.2728    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    6.5864    3.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689    5.1979    1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772    5.8527    3.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    4.7638    4.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    3.6724    3.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9925    4.5332    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741    3.1382    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217    2.2717    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532    1.5338    3.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0306    0.7551    2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    2.7984    4.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044    1.0603    4.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590    3.2035    2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    2.4824    3.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524    1.5394    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9595    0.9609    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.0459    3.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -0.4894    3.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -2.4899    3.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -3.3293    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835   -3.3689    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -4.1021    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9373   -0.8694   -1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2894   -2.6388   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0598   -0.5112   -4.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5247   -2.2222   -4.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569   -1.7368   -2.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494   -1.2311   -4.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6696   -0.1159   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2293   -0.1306   -5.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2140   -1.5075   -6.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.6320   -6.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842   -3.6900   -5.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714   -3.2815   -4.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -3.6743   -3.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -4.9736    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2 54  1  0
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  1 51  1  0
  1 52  1  0
  1 53  1  0
M  CHG  2  26  -1  30   1
M  END


  Mrv0541 02251206132D          

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  1  2  1  0  0  0  0
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 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 16 51  1  1  0  0  0
 18 52  1  1  0  0  0
M  CHG  2  22  -1  27   1
M  END
> <DATABASE_ID>
NP0091902

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h16,18,39-40,44H,6-15,17,19-38H2,1-5H3,(H-,42,45,46,47)/t39-,40+/m0/s1

> <INCHI_KEY>
HHAUPBIWIXBMEU-IOLBBIBUSA-N

> <FORMULA>
C41H83N2O6P

> <MOLECULAR_WEIGHT>
731.0813

> <EXACT_MASS>
730.59887491

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
92.99917814785692

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R)-3-hydroxy-2-(octadec-11-enamido)octadecyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
8.797213657972101

> <ALOGPS_LOGS>
-7.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.700289304677696

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.871228359113159

> <JCHEM_PKA_STRONGEST_BASIC>
0.025414091912352887

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
223.2979

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R)-3-hydroxy-2-(octadec-11-enamido)octadecyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      28.696  18.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.030  17.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.364  18.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.697  17.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.031  18.108   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.365  17.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.698  18.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.032  17.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.366  18.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.699  17.338   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.033  18.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.367  17.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      44.701  18.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.034  17.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.368  18.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.702  17.338   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      48.702  15.798   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      50.035  18.108   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      50.035  19.648   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      51.369  20.418   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      51.369  21.958   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      49.829  21.958   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      52.909  21.958   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      51.369  23.498   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      52.703  24.268   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      52.703  25.808   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      54.036  26.578   0.000  0.00  0.00           N+1
HETATM   28  C   UNK     0      54.806  25.244   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      53.266  27.912   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      55.370  27.348   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      51.369  17.338   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      52.703  18.108   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      52.703  19.648   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      54.036  17.338   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      55.370  18.108   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      56.704  17.338   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      58.037  18.108   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      59.371  17.338   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      60.705  18.108   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      62.038  17.338   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      63.372  18.108   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      64.706  17.338   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      66.039  18.108   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      67.373  17.338   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      68.707  18.108   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      68.707  19.648   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      70.040  20.418   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      70.040  21.958   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      71.374  22.728   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      71.374  24.268   0.000  0.00  0.00           C+0
HETATM   51  H   UNK     0      47.368  16.568   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      51.369  18.878   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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   18   51                                             
CONECT   17   16                                                            
CONECT   18   16   19   31   52                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   18   32                                                       
CONECT   32   31   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                                                            
CONECT   51   16                                                            
CONECT   52   18                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  102    0
END

View in JSmol

Synonyms

Value	Source
Sphingomyelin	MetBuilder
N-(11Z-Octadecenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/18:1(11Z))	MetBuilder
N-(11Z-Octadecenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(11Z-Octadecenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₄₁H₈₃N₂O₆P

Average Mass

731.0813 Da

Monoisotopic Mass

730.59887 Da

IUPAC Name

(2-{[(2S,3R)-3-hydroxy-2-(octadec-11-enamido)octadecyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-3-hydroxy-2-(octadec-11-enamido)octadecyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h16,18,39-40,44H,6-15,17,19-38H2,1-5H3,(H-,42,45,46,47)/t39-,40+/m0/s1

InChI Key

HHAUPBIWIXBMEU-IOLBBIBUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic zwitterion
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.41	ALOGPS
logP	8.8	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.025	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	38	ChemAxon
Refractivity	223.3 m³·mol⁻¹	ChemAxon
Polarizability	93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028755

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for SM(d18:0/18:1(11Z)) (NP0091902)

MOL for NP0091902 (SM(d18:0/18:1(11Z)))

3D MOL for NP0091902 (SM(d18:0/18:1(11Z)))

3D SDF for NP0091902 (SM(d18:0/18:1(11Z)))

3D-SDF for NP0091902 (SM(d18:0/18:1(11Z)))

PDB for NP0091902 (SM(d18:0/18:1(11Z)))

3D PDB for NP0091902 (SM(d18:0/18:1(11Z)))

SMILES for NP0091902 (SM(d18:0/18:1(11Z)))

INCHI for NP0091902 (SM(d18:0/18:1(11Z)))

Structure for NP0091902 (SM(d18:0/18:1(11Z)))

3D Structure for NP0091902 (SM(d18:0/18:1(11Z)))