NP-MRD: Showing NP-Card for SM(d19:1/24:1(15Z)) (NP0091569)

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Record Information

Version

2.0

Created at

2022-05-11 18:41:33 UTC

Updated at

2022-05-11 18:41:33 UTC

NP-MRD ID

NP0091569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

SM(d19:1/24:1(15Z))

Description

SM(d19:1/24:1(15Z)) 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(d19:1/24:1(15Z)) consists of an unsaturated 19-carbon sphingoid base with an attached unsaturated 15Z-tetracosenoyl 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 02251204262D          

 59 58  0  0  1  0            999 V2000
    1.2375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000   -5.7158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3125   -6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3125   -5.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3125   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000   -2.8579    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.6145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375   -5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5500   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7875   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -6.4303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250   -4.2868    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
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 22 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
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 19 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 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
 48 47  1  4  0  0  0
 48 49  2  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
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 17 58  1  1  0  0  0
 19 59  1  1  0  0  0
M  CHG  1  28   1
M  END

     RDKit          3D

153152  0  0  0  0  0  0  0  0999 V2000
    2.6615    1.8027    5.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108    2.0377    4.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2863    3.5237    4.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    3.8753    3.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    5.3622    3.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    5.7758    2.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8252    5.3272    1.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    5.8756    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    5.5136   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366    4.8108   -1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8164    4.2381   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    2.7431   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041    2.0885   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5767    0.5977   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2685   -0.1048   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7286    0.3556   -1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.3464   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843    0.0157   -2.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -0.3219   -3.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -1.8190   -3.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -2.3719   -5.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -3.8732   -4.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746   -4.2341   -3.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -3.7525   -4.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -3.3865   -5.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -3.6919   -3.5378 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.2691   -3.7963 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0669   -1.7727   -3.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2901   -1.2091   -4.8419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880    0.4245   -5.0196 P   0  0  1  0  0  5  0  0  0  0  0  0
    3.2453    1.0928   -3.8997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    0.7829   -6.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    1.2644   -5.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551    1.1823   -6.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7245    1.9341   -6.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280    1.9493   -7.9233 N   0  0  1  0  0  4  0  0  0  0  0  0
   -0.8584    3.0473   -8.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2691    0.7152   -8.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596    2.2327   -7.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -4.0152   -2.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7963   -5.3905   -3.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971   -3.9149   -1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9163   -4.6242   -0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4435   -4.4653    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464   -4.0278    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339   -3.9075    3.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2994   -5.1992    3.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -5.0789    5.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029   -4.1111    5.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -4.0876    6.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -3.1363    6.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -3.5318    5.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183   -2.5636    5.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377   -3.0746    4.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620   -2.2214    4.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144   -2.8070    3.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0240   -2.8391    2.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781    2.2141    5.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    2.3623    6.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952    0.7049    5.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734    1.5511    4.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7391    1.5817    3.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366    3.9788    4.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617    3.9152    5.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    3.4641    4.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    3.4284    2.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2789    5.7625    4.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9450    5.9040    3.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728    5.3142    2.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529    6.8795    2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9264    4.2275    1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445    5.7502    0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    7.0037    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224    5.6574    1.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    5.8792   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    4.6004   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7982    4.6900   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7044    4.3783    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1766    2.5257   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    2.3098    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    2.3236    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    2.5339   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9365    0.4760   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    0.1805    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -1.1905   -0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295    0.0003    0.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972    1.4352   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.1733   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8703   -1.4227   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -0.0307   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  1  36   1
M  END


  Mrv0541 02251204262D          

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M  CHG  1  28   1
M  END
> <DATABASE_ID>
NP0091569

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C48H95N2O6P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-28-30-32-34-36-38-40-42-48(52)49-46(45-56-57(53,54)55-44-43-50(3,4)5)47(51)41-39-37-35-33-31-29-21-19-17-15-13-11-9-7-2/h20,22,39,41,46-47,51H,6-19,21,23-38,40,42-45H2,1-5H3,(H-,49,52,53,54)/p+1/t46-,47+/m0/s1

> <INCHI_KEY>
BJXQFQDUJVIUAH-KBRGEABDSA-O

> <FORMULA>
C48H96N2O6P

> <MOLECULAR_WEIGHT>
828.2594

> <EXACT_MASS>
827.700600326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
107.98406041028406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,3R)-3-hydroxy-2-(tetracos-15-enamido)nonadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

> <ALOGPS_LOGP>
6.42

> <JCHEM_LOGP>
11.704598164528413

> <ALOGPS_LOGS>
-7.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.499201320641198

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8709150288593719

> <JCHEM_PKA_STRONGEST_BASIC>
0.011796153944252485

> <JCHEM_POLAR_SURFACE_AREA>
105.09

> <JCHEM_REFRACTIVITY>
257.5892

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.03e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R)-3-hydroxy-2-(tetracos-15-enamido)nonadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid

> <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       2.310  -9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080  -8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.390  -6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.700  -8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.240  -8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.010  -9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.550  -9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.320 -10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.860 -10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.630  -9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.170  -9.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.940 -10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.480 -10.669   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.250 -12.003   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      19.250  -9.336   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.480  -8.002   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      19.250  -6.668   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      18.480  -5.335   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      17.146  -6.105   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      19.814  -4.565   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.710  -4.001   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.480  -2.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.710  -1.334   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      18.480   0.000   0.000  0.00  0.00           N+1
HETATM   29  C   UNK     0      19.814  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.146   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.250   1.334   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      20.790  -9.336   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      21.560  -8.002   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.790  -6.668   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      23.100  -8.002   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.870  -6.668   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.410  -6.668   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      26.180  -5.335   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      27.720  -5.335   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.490  -4.001   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      30.030  -4.001   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      30.800  -2.667   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      32.340  -2.667   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      33.110  -1.334   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      34.650  -1.334   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      35.420   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      36.960   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.730   1.334   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      39.270   1.334   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      40.040   2.667   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      41.580   2.667   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      42.350   1.334   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      43.890   1.334   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      44.660   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      46.200   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      46.970  -1.334   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      48.510  -1.334   0.000  0.00  0.00           C+0
HETATM   58  H   UNK     0      17.710 -12.003   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      20.020  -8.002   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                                                       
CONECT   17   16   18   19   58                                             
CONECT   18   17                                                            
CONECT   19   17   20   32   59                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   19   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   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   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   17                                                            
CONECT   59   19                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  116    0
END

View in JSmol

Synonyms

Value	Source
Sphingomyelin	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecasphing-4-enine	MetBuilder
Sphingomyelin(D19:1/24:1(15Z))	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecasphingosine	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecad-erythro-sphingosine	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadeca4-sphingenine	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecad-sphingosine	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecasphingenine	MetBuilder
N-(15Z-Tetracosenoyl)-1-phosphocholine-nonadecaerythro-4-sphingenine	MetBuilder

Chemical Formula

C₄₈H₉₆N₂O₆P

Average Mass

828.2594 Da

Monoisotopic Mass

827.70060 Da

IUPAC Name

{[(2S,3R)-3-hydroxy-2-(tetracos-15-enamido)nonadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

Traditional Name

[(2S,3R)-3-hydroxy-2-(tetracos-15-enamido)nonadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(C=CCCCCCCCCCCCCCC)[C@]([H])(COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCC=CCCCCCCCC

InChI Identifier

InChI=1S/C48H95N2O6P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-28-30-32-34-36-38-40-42-48(52)49-46(45-56-57(53,54)55-44-43-50(3,4)5)47(51)41-39-37-35-33-31-29-21-19-17-15-13-11-9-7-2/h20,22,39,41,46-47,51H,6-19,21,23-38,40,42-45H2,1-5H3,(H-,49,52,53,54)/p+1/t46-,47+/m0/s1

InChI Key

BJXQFQDUJVIUAH-KBRGEABDSA-O

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 acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
N-acyl-amine
Fatty amide
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Organic cation
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	6.42	ALOGPS
logP	11.7	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.012	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.09 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	257.59 m³·mol⁻¹	ChemAxon
Polarizability	107.98 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

FDB028385

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(d19:1/24:1(15Z)) (NP0091569)

MOL for NP0091569 (SM(d19:1/24:1(15Z)))

3D MOL for NP0091569 (SM(d19:1/24:1(15Z)))

3D SDF for NP0091569 (SM(d19:1/24:1(15Z)))

3D-SDF for NP0091569 (SM(d19:1/24:1(15Z)))

PDB for NP0091569 (SM(d19:1/24:1(15Z)))

3D PDB for NP0091569 (SM(d19:1/24:1(15Z)))

SMILES for NP0091569 (SM(d19:1/24:1(15Z)))

INCHI for NP0091569 (SM(d19:1/24:1(15Z)))

Structure for NP0091569 (SM(d19:1/24:1(15Z)))

3D Structure for NP0091569 (SM(d19:1/24:1(15Z)))