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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (61) Show 61 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-29 14:20:42 UTC

Update Date

2022-11-30 19:03:55 UTC

HMDB ID

HMDB0011145

Secondary Accession Numbers

HMDB11145

Metabolite Identification

Common Name

PA(O-16:0/18:0)

Description

2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is an intermediate in ether lipid metabolism. 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is converted from 1-octadecyl-glycerone-3-phosphate via 1-acylglycerol-3-phosphate O-acyltransferase. (EC: 2.3.1.51). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked bilayers.

Structure

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

m4
  Mrv1572012171518022D          

 46 45  0  0  1  0            999 V2000
   -0.1691    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8792    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    0.6480    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1560    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8701    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5843    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2984    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0125    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7266    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4407    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1549    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8690    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5831    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2972    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0113    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8941   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6082   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3223   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0364   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7505   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4646   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1788   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8929   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6070   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3212   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0353   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7494   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4635   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 12  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 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
 28  5  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 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
M  END

HMDB0011145
     RDKit          3D
PA(O-16:0/18:0)
120119  0  0  0  0  0  0  0  0999 V2000
  -15.8611   -0.3878   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9092    0.8937   -1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3737    2.0668   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9221    1.8606   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0981    1.6959   -1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6435    1.4656   -1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1054    2.6009   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6865    2.4717   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2171    1.4361    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3406   -0.0004    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7023   -0.4734   -0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2384   -0.2507   -0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4978   -0.9571    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9751   -0.7317    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2412   -1.4238    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.2958    1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    0.1354    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7966    0.0864    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705    1.1901    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -1.0639    1.2474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671   -1.1103    1.2788 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9595   -1.8885    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654   -1.9535    0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2064   -1.0499   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875    0.2296    0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4604    1.0767    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643    1.6288   -0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.6913   -1.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4722   -0.1061   -1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354   -1.0973   -2.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1821   -1.8641   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3197   -0.9753   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3945   -1.8668   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5671   -1.0891   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1985   -0.2992   -1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3882    0.5085   -0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9789    1.4833    0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9460    2.4713   -0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6200    3.3830    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198   -1.6742    2.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -2.9592    2.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -3.6201    4.2770 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7860   -3.2505    5.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813   -5.3160    4.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131   -3.0786    4.7560 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0130   -0.2146    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6478   -1.0532   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8932   -0.9190   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9891    1.1213   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3938    0.7767   -2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9553    2.2620    0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4017    2.9668   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6231    2.8307    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8008    1.0772    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3815    0.8614   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1137    2.6719   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5680    0.5324   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0613    1.3896   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1795    3.5829   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6858    2.7852    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4260    3.4844    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0952    2.4996   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7953    1.5948    1.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1573    1.6802    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3077   -0.4814    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7065   -0.5123    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2695   -0.1460   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8480   -1.5981   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508    0.8241   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9254   -0.7110   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6371   -2.0686    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7906   -0.6943    1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7353   -1.1044   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367    0.3483    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6981   -1.1589    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719   -2.5232    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659   -1.8206    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -1.8569    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.7363    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168    0.6075    2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.0738    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -1.4746   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -2.9420    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.9006   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.5709    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    0.9113    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215    0.0343    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.9971    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717    0.6238    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    2.3791   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7624    2.3392   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    1.3475   -2.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066    0.0675   -2.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2872   -0.5571   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.6633   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3922   -0.5922   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942   -1.8619   -2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5247   -2.6684   -2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7342   -2.4119   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7353   -0.4790   -2.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9216   -0.2650   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9295   -2.4365    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6969   -2.5896   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2850   -1.8318    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1841   -0.3996    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4930    0.4052   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5264   -0.9860   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8345    1.0826   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1567   -0.1740   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8856    2.0513    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325    0.9644    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3513    3.1309   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0301    2.0162   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2194    4.3149    0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8390    2.8649    1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5182    3.5802    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

m4
  Mrv1572012171518022D          

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M  END
> <DATABASE_ID>
HMDB0011145

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C37H75O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36H,3-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1

> <INCHI_KEY>
BIMPCBJDAYKNLD-PSXMRANNSA-N

> <FORMULA>
C37H75O7P

> <MOLECULAR_WEIGHT>
662.974

> <EXACT_MASS>
662.525041753

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
84.1898855917419

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
9.40

> <JCHEM_LOGP>
13.149460676666665

> <ALOGPS_LOGS>
-6.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.344941703576107

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3191155385434845

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1410029745884644

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
188.01919999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.40e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011145
     RDKit          3D
PA(O-16:0/18:0)
120119  0  0  0  0  0  0  0  0999 V2000
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   -2.3622   -1.8569    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.7363    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168    0.6075    2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.0738    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -1.4746   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -2.9420    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.9006   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.5709    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    0.9113    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215    0.0343    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.9971    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717    0.6238    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    2.3791   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7624    2.3392   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    1.3475   -2.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066    0.0675   -2.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2872   -0.5571   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.6633   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3922   -0.5922   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942   -1.8619   -2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5247   -2.6684   -2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7342   -2.4119   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7353   -0.4790   -2.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9216   -0.2650   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9295   -2.4365    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6969   -2.5896   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2850   -1.8318    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1841   -0.3996    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4930    0.4052   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5264   -0.9860   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8345    1.0826   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1567   -0.1740   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8856    2.0513    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325    0.9644    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3513    3.1309   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0301    2.0162   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2194    4.3149    0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8390    2.8649    1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5182    3.5802    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -1.0175    3.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -1.6910    2.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -5.6288    3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183   -3.5845    4.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
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 44119  1  0
 45120  1  0
M  END

HEADER    PROTEIN                                 17-DEC-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: m4                                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-DEC-15         0                                  
HETATM    1  C   UNK     0      -0.316   0.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.641   1.436   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.967   0.673   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0       0.451  -0.652   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0      -1.082  -0.652   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.010   1.439   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.336   0.673   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.618   0.641   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       4.222   1.210   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       3.547   0.039   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.222   2.605   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.293   1.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.626   0.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.959   1.436   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.292   0.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.625   1.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.958   0.665   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.291   1.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.624   0.665   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.957   1.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -16.290   0.665   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -17.623   1.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -18.956   0.665   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -20.289   1.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -21.622   0.665   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -22.955   1.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -24.288   0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.471  -1.436   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.471  -2.876   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.804  -0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.137  -1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.470  -0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.803  -1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.136  -0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -10.469  -1.436   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -11.802  -0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -13.135  -1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -14.468  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -15.801  -1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -17.134  -0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -18.467  -1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -19.800  -0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -21.133  -1.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -22.466  -0.665   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -23.799  -1.436   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -25.132  -0.665   0.000  0.00  0.00           C+0
CONECT    1    2    5    4    6                                             
CONECT    2    1    3                                                       
CONECT    3    2   12                                                       
CONECT    4    1                                                            
CONECT    5    1   28                                                       
CONECT    6    1    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    8   10   11    7                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   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                                                            
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   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                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   90    0
END

COMPND    HMDB0011145
HETATM    1  C1  UNL     1     -15.861  -0.388  -0.908  1.00  0.00           C  
HETATM    2  C2  UNL     1     -15.909   0.894  -1.678  1.00  0.00           C  
HETATM    3  C3  UNL     1     -15.374   2.067  -0.889  1.00  0.00           C  
HETATM    4  C4  UNL     1     -13.922   1.861  -0.474  1.00  0.00           C  
HETATM    5  C5  UNL     1     -13.098   1.696  -1.702  1.00  0.00           C  
HETATM    6  C6  UNL     1     -11.644   1.466  -1.303  1.00  0.00           C  
HETATM    7  C7  UNL     1     -11.105   2.601  -0.536  1.00  0.00           C  
HETATM    8  C8  UNL     1      -9.687   2.472  -0.141  1.00  0.00           C  
HETATM    9  C9  UNL     1      -9.217   1.436   0.772  1.00  0.00           C  
HETATM   10  C10 UNL     1      -9.341  -0.000   0.477  1.00  0.00           C  
HETATM   11  C11 UNL     1      -8.702  -0.473  -0.780  1.00  0.00           C  
HETATM   12  C12 UNL     1      -7.238  -0.251  -0.909  1.00  0.00           C  
HETATM   13  C13 UNL     1      -6.498  -0.957   0.191  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.975  -0.732   0.023  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.241  -1.424   1.135  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.765  -1.296   1.118  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.279   0.135   1.186  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.797   0.086   1.206  1.00  0.00           C  
HETATM   19  O1  UNL     1      -0.171   1.190   1.185  1.00  0.00           O  
HETATM   20  O2  UNL     1      -0.062  -1.064   1.247  1.00  0.00           O  
HETATM   21  C19 UNL     1       1.367  -1.110   1.279  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.959  -1.888   0.144  1.00  0.00           C  
HETATM   23  O3  UNL     1       3.265  -1.954   0.143  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.206  -1.050  -0.106  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.288   0.230   0.602  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.460   1.077   0.366  1.00  0.00           C  
HETATM   27  C24 UNL     1       5.864   1.629  -0.915  1.00  0.00           C  
HETATM   28  C25 UNL     1       6.300   0.691  -1.985  1.00  0.00           C  
HETATM   29  C26 UNL     1       7.472  -0.106  -1.437  1.00  0.00           C  
HETATM   30  C27 UNL     1       8.035  -1.097  -2.399  1.00  0.00           C  
HETATM   31  C28 UNL     1       9.182  -1.864  -1.779  1.00  0.00           C  
HETATM   32  C29 UNL     1      10.320  -0.975  -1.332  1.00  0.00           C  
HETATM   33  C30 UNL     1      11.395  -1.867  -0.741  1.00  0.00           C  
HETATM   34  C31 UNL     1      12.567  -1.089  -0.235  1.00  0.00           C  
HETATM   35  C32 UNL     1      13.198  -0.299  -1.328  1.00  0.00           C  
HETATM   36  C33 UNL     1      14.388   0.509  -0.842  1.00  0.00           C  
HETATM   37  C34 UNL     1      13.979   1.483   0.242  1.00  0.00           C  
HETATM   38  C35 UNL     1      12.946   2.471  -0.219  1.00  0.00           C  
HETATM   39  C36 UNL     1      12.620   3.383   0.952  1.00  0.00           C  
HETATM   40  C37 UNL     1       1.820  -1.674   2.625  1.00  0.00           C  
HETATM   41  O4  UNL     1       1.309  -2.959   2.816  1.00  0.00           O  
HETATM   42  P1  UNL     1       1.777  -3.620   4.277  1.00  0.00           P  
HETATM   43  O5  UNL     1       0.786  -3.250   5.382  1.00  0.00           O  
HETATM   44  O6  UNL     1       1.781  -5.316   4.166  1.00  0.00           O  
HETATM   45  O7  UNL     1       3.313  -3.079   4.756  1.00  0.00           O  
HETATM   46  H1  UNL     1     -16.013  -0.215   0.179  1.00  0.00           H  
HETATM   47  H2  UNL     1     -16.648  -1.053  -1.286  1.00  0.00           H  
HETATM   48  H3  UNL     1     -14.893  -0.919  -1.007  1.00  0.00           H  
HETATM   49  H4  UNL     1     -16.989   1.121  -1.858  1.00  0.00           H  
HETATM   50  H5  UNL     1     -15.394   0.777  -2.630  1.00  0.00           H  
HETATM   51  H6  UNL     1     -15.955   2.262   0.017  1.00  0.00           H  
HETATM   52  H7  UNL     1     -15.402   2.967  -1.526  1.00  0.00           H  
HETATM   53  H8  UNL     1     -13.623   2.831   0.023  1.00  0.00           H  
HETATM   54  H9  UNL     1     -13.801   1.077   0.279  1.00  0.00           H  
HETATM   55  H10 UNL     1     -13.382   0.861  -2.341  1.00  0.00           H  
HETATM   56  H11 UNL     1     -13.114   2.672  -2.260  1.00  0.00           H  
HETATM   57  H12 UNL     1     -11.568   0.532  -0.764  1.00  0.00           H  
HETATM   58  H13 UNL     1     -11.061   1.390  -2.263  1.00  0.00           H  
HETATM   59  H14 UNL     1     -11.180   3.583  -1.107  1.00  0.00           H  
HETATM   60  H15 UNL     1     -11.686   2.785   0.422  1.00  0.00           H  
HETATM   61  H16 UNL     1      -9.426   3.484   0.350  1.00  0.00           H  
HETATM   62  H17 UNL     1      -9.095   2.500  -1.115  1.00  0.00           H  
HETATM   63  H18 UNL     1      -9.795   1.595   1.757  1.00  0.00           H  
HETATM   64  H19 UNL     1      -8.157   1.680   1.138  1.00  0.00           H  
HETATM   65  H20 UNL     1     -10.308  -0.481   0.642  1.00  0.00           H  
HETATM   66  H21 UNL     1      -8.706  -0.512   1.317  1.00  0.00           H  
HETATM   67  H22 UNL     1      -9.269  -0.146  -1.699  1.00  0.00           H  
HETATM   68  H23 UNL     1      -8.848  -1.598  -0.797  1.00  0.00           H  
HETATM   69  H24 UNL     1      -6.951   0.824  -0.910  1.00  0.00           H  
HETATM   70  H25 UNL     1      -6.925  -0.711  -1.892  1.00  0.00           H  
HETATM   71  H26 UNL     1      -6.637  -2.069   0.103  1.00  0.00           H  
HETATM   72  H27 UNL     1      -6.791  -0.694   1.207  1.00  0.00           H  
HETATM   73  H28 UNL     1      -4.735  -1.104  -0.969  1.00  0.00           H  
HETATM   74  H29 UNL     1      -4.737   0.348   0.066  1.00  0.00           H  
HETATM   75  H30 UNL     1      -4.698  -1.159   2.123  1.00  0.00           H  
HETATM   76  H31 UNL     1      -4.472  -2.523   1.020  1.00  0.00           H  
HETATM   77  H32 UNL     1      -2.366  -1.821   0.221  1.00  0.00           H  
HETATM   78  H33 UNL     1      -2.362  -1.857   1.985  1.00  0.00           H  
HETATM   79  H34 UNL     1      -2.659   0.736   0.324  1.00  0.00           H  
HETATM   80  H35 UNL     1      -2.717   0.608   2.088  1.00  0.00           H  
HETATM   81  H36 UNL     1       1.685  -0.074   1.249  1.00  0.00           H  
HETATM   82  H37 UNL     1       1.509  -1.475  -0.836  1.00  0.00           H  
HETATM   83  H38 UNL     1       1.541  -2.942   0.119  1.00  0.00           H  
HETATM   84  H39 UNL     1       4.217  -0.901  -1.244  1.00  0.00           H  
HETATM   85  H40 UNL     1       5.212  -1.571   0.048  1.00  0.00           H  
HETATM   86  H41 UNL     1       3.399   0.911   0.352  1.00  0.00           H  
HETATM   87  H42 UNL     1       4.222   0.034   1.699  1.00  0.00           H  
HETATM   88  H43 UNL     1       5.298   1.997   1.065  1.00  0.00           H  
HETATM   89  H44 UNL     1       6.372   0.624   0.921  1.00  0.00           H  
HETATM   90  H45 UNL     1       5.100   2.379  -1.328  1.00  0.00           H  
HETATM   91  H46 UNL     1       6.762   2.339  -0.774  1.00  0.00           H  
HETATM   92  H47 UNL     1       6.730   1.347  -2.854  1.00  0.00           H  
HETATM   93  H48 UNL     1       5.607   0.068  -2.488  1.00  0.00           H  
HETATM   94  H49 UNL     1       7.287  -0.557  -0.456  1.00  0.00           H  
HETATM   95  H50 UNL     1       8.275   0.663  -1.265  1.00  0.00           H  
HETATM   96  H51 UNL     1       8.392  -0.592  -3.323  1.00  0.00           H  
HETATM   97  H52 UNL     1       7.294  -1.862  -2.724  1.00  0.00           H  
HETATM   98  H53 UNL     1       9.525  -2.668  -2.467  1.00  0.00           H  
HETATM   99  H54 UNL     1       8.734  -2.412  -0.906  1.00  0.00           H  
HETATM  100  H55 UNL     1      10.735  -0.479  -2.223  1.00  0.00           H  
HETATM  101  H56 UNL     1       9.922  -0.265  -0.586  1.00  0.00           H  
HETATM  102  H57 UNL     1      10.930  -2.436   0.095  1.00  0.00           H  
HETATM  103  H58 UNL     1      11.697  -2.590  -1.519  1.00  0.00           H  
HETATM  104  H59 UNL     1      13.285  -1.832   0.198  1.00  0.00           H  
HETATM  105  H60 UNL     1      12.184  -0.400   0.555  1.00  0.00           H  
HETATM  106  H61 UNL     1      12.493   0.405  -1.774  1.00  0.00           H  
HETATM  107  H62 UNL     1      13.526  -0.986  -2.133  1.00  0.00           H  
HETATM  108  H63 UNL     1      14.834   1.083  -1.670  1.00  0.00           H  
HETATM  109  H64 UNL     1      15.157  -0.174  -0.435  1.00  0.00           H  
HETATM  110  H65 UNL     1      14.886   2.051   0.532  1.00  0.00           H  
HETATM  111  H66 UNL     1      13.632   0.964   1.156  1.00  0.00           H  
HETATM  112  H67 UNL     1      13.351   3.131  -1.013  1.00  0.00           H  
HETATM  113  H68 UNL     1      12.030   2.016  -0.630  1.00  0.00           H  
HETATM  114  H69 UNL     1      13.219   4.315   0.944  1.00  0.00           H  
HETATM  115  H70 UNL     1      12.839   2.865   1.908  1.00  0.00           H  
HETATM  116  H71 UNL     1      11.518   3.580   0.909  1.00  0.00           H  
HETATM  117  H72 UNL     1       1.442  -1.018   3.403  1.00  0.00           H  
HETATM  118  H73 UNL     1       2.917  -1.691   2.616  1.00  0.00           H  
HETATM  119  H74 UNL     1       1.871  -5.629   3.237  1.00  0.00           H  
HETATM  120  H75 UNL     1       4.018  -3.585   4.279  1.00  0.00           H  
CONECT    1    2   46   47   48
CONECT    2    3   49   50
CONECT    3    4   51   52
CONECT    4    5   53   54
CONECT    5    6   55   56
CONECT    6    7   57   58
CONECT    7    8   59   60
CONECT    8    9   61   62
CONECT    9   10   63   64
CONECT   10   11   65   66
CONECT   11   12   67   68
CONECT   12   13   69   70
CONECT   13   14   71   72
CONECT   14   15   73   74
CONECT   15   16   75   76
CONECT   16   17   77   78
CONECT   17   18   79   80
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   40   81
CONECT   22   23   82   83
CONECT   23   24
CONECT   24   25   84   85
CONECT   25   26   86   87
CONECT   26   27   88   89
CONECT   27   28   90   91
CONECT   28   29   92   93
CONECT   29   30   94   95
CONECT   30   31   96   97
CONECT   31   32   98   99
CONECT   32   33  100  101
CONECT   33   34  102  103
CONECT   34   35  104  105
CONECT   35   36  106  107
CONECT   36   37  108  109
CONECT   37   38  110  111
CONECT   38   39  112  113
CONECT   39  114  115  116
CONECT   40   41  117  118
CONECT   41   42
CONECT   42   43   43   44   45
CONECT   44  119
CONECT   45  120
END

HMDB0011145
     RDKit          3D
PA(O-16:0/18:0)
120119  0  0  0  0  0  0  0  0999 V2000
  -15.8611   -0.3878   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9092    0.8937   -1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3737    2.0668   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9221    1.8606   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0981    1.6959   -1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6435    1.4656   -1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1054    2.6009   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6865    2.4717   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2171    1.4361    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3406   -0.0004    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7023   -0.4734   -0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2384   -0.2507   -0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4978   -0.9571    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9751   -0.7317    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2412   -1.4238    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.2958    1.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    0.1354    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7966    0.0864    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705    1.1901    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -1.0639    1.2474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671   -1.1103    1.2788 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9595   -1.8885    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654   -1.9535    0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2064   -1.0499   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875    0.2296    0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4604    1.0767    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643    1.6288   -0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.6913   -1.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4722   -0.1061   -1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354   -1.0973   -2.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1821   -1.8641   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3197   -0.9753   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3945   -1.8668   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5671   -1.0891   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1985   -0.2992   -1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3882    0.5085   -0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9789    1.4833    0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9460    2.4713   -0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6200    3.3830    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198   -1.6742    2.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -2.9592    2.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -3.6201    4.2770 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7860   -3.2505    5.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813   -5.3160    4.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131   -3.0786    4.7560 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0130   -0.2146    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6478   -1.0532   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8932   -0.9190   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9891    1.1213   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3938    0.7767   -2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9553    2.2620    0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4017    2.9668   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6231    2.8307    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8008    1.0772    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3815    0.8614   -2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1137    2.6719   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5680    0.5324   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0613    1.3896   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1795    3.5829   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6858    2.7852    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4260    3.4844    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0952    2.4996   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7953    1.5948    1.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1573    1.6802    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3077   -0.4814    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7065   -0.5123    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2695   -0.1460   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8480   -1.5981   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508    0.8241   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9254   -0.7110   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6371   -2.0686    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7906   -0.6943    1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7353   -1.1044   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367    0.3483    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6981   -1.1589    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719   -2.5232    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659   -1.8206    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -1.8569    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.7363    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168    0.6075    2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.0738    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -1.4746   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -2.9420    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.9006   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.5709    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    0.9113    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215    0.0343    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.9971    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717    0.6238    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    2.3791   -1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7624    2.3392   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    1.3475   -2.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066    0.0675   -2.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2872   -0.5571   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    0.6633   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3922   -0.5922   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942   -1.8619   -2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5247   -2.6684   -2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7342   -2.4119   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7353   -0.4790   -2.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9216   -0.2650   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9295   -2.4365    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6969   -2.5896   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2850   -1.8318    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1841   -0.3996    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4930    0.4052   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5264   -0.9860   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8345    1.0826   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1567   -0.1740   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8856    2.0513    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325    0.9644    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3513    3.1309   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0301    2.0162   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2194    4.3149    0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8390    2.8649    1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5182    3.5802    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -1.0175    3.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -1.6910    2.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -5.6288    3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183   -3.5845    4.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 21 40  1  0
 40 41  1  0
 41 42  1  0
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 42 44  1  0
 42 45  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  3 51  1  0
  3 52  1  0
  4 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  6 57  1  0
  6 58  1  0
  7 59  1  0
  7 60  1  0
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  8 62  1  0
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 31 98  1  0
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 32100  1  0
 32101  1  0
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 33103  1  0
 34104  1  0
 34105  1  0
 35106  1  0
 35107  1  0
 36108  1  0
 36109  1  0
 37110  1  0
 37111  1  0
 38112  1  0
 38113  1  0
 39114  1  0
 39115  1  0
 39116  1  0
 40117  1  0
 40118  1  0
 44119  1  0
 45120  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate	HMDB
PA(O-16:0/18:0)	HMDB

Chemical Formula

C₃₇H₇₅O₇P

Average Molecular Weight

662.974

Monoisotopic Molecular Weight

662.525041753

IUPAC Name

[(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C37H75O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36H,3-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1

InChI Key

BIMPCBJDAYKNLD-PSXMRANNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphates. These are glycerophosphates in which the O-1 atom of the glycerol is bonded to a fatty acid (saturated or unsaturated) through an ether linkage, and the O-2 atom is bonded to another fatty acid through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-alkyl,2-acylglycerophosphates

Alternative Parents

Substituents

1-alkyl,2-acyl-glycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Glycerol ether
Organic phosphoric acid derivative
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-alkyl,2-acylglycerophosphates (LMGP10020082 )

Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0011145)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0011145)
Extracellular (HMDB: HMDB0011145)
Cell membrane (HMDB: HMDB0011145)
Intracellular membrane (HMDB: HMDB0011145)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011145)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011145)

Source

Endogenous

Endogenous (HMDB: HMDB0011145)

Animal

Animal (HMDB: HMDB0011145)

Exogenous

Food

Food (HMDB: HMDB0011145)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0011145)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0011145)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0011145)

Lipid metabolism pathway (HMDB: HMDB0011145)

Cellular process

Cell signaling (HMDB: HMDB0011145)

Biochemical process

Lipid transport (HMDB: HMDB0011145)

Role

Biological role

Energy source (HMDB: HMDB0011145)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0011145)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0011145)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.4e-05 g/L	ALOGPS
logP	9.4	ALOGPS
logP	13.15	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	188.02 m³·mol⁻¹	ChemAxon
Polarizability	84.19 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
DarkChem	[M+H]+	270.145	31661259
DarkChem	[M-H]-	261.957	31661259
DeepCCS	[M+H]+	255.261	30932474
DeepCCS	[M-H]-	252.903	30932474
DeepCCS	[M-2H]-	286.119	30932474
DeepCCS	[M+Na]+	261.355	30932474
AllCCS	[M+H]+	277.1	32859911
AllCCS	[M+H-H2O]+	276.8	32859911
AllCCS	[M+NH4]+	277.4	32859911
AllCCS	[M+Na]+	277.5	32859911
AllCCS	[M-H]-	261.4	32859911
AllCCS	[M+Na-2H]-	265.7	32859911
AllCCS	[M+HCOO]-	270.5	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.	10.43 minutes	32390414
Predicted by Siyang on May 30, 2022	34.077 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	74.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4882.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	628.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	370.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	248.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	966.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1685.0 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	1547.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	226.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3407.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1029.4 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	2787.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1326.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	702.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	791.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	790.0 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PA(O-16:0/18:0)	[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC	4201.2	Standard polar	33892256
PA(O-16:0/18:0)	[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC	3875.9	Standard non polar	33892256
PA(O-16:0/18:0)	[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC	4751.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PA(O-16:0/18:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C	4634.2	Semi standard non polar	33892256
PA(O-16:0/18:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C	4264.4	Standard non polar	33892256
PA(O-16:0/18:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C	5569.9	Standard polar	33892256
PA(O-16:0/18:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4597.7	Semi standard non polar	33892256
PA(O-16:0/18:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4255.8	Standard non polar	33892256
PA(O-16:0/18:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4852.6	Standard polar	33892256
PA(O-16:0/18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C	4900.7	Semi standard non polar	33892256
PA(O-16:0/18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C	4361.3	Standard non polar	33892256
PA(O-16:0/18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C	5531.6	Standard polar	33892256
PA(O-16:0/18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	5147.7	Semi standard non polar	33892256
PA(O-16:0/18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4459.9	Standard non polar	33892256
PA(O-16:0/18:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4943.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PA(O-16:0/18:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9362652000-e3c1e1e26c9d0956f777	2017-09-01	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 - PA(O-16:0/18:0) 10V, Positive-QTOF	splash10-02vj-0095035000-abc1e4ed109c621aad65	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 20V, Positive-QTOF	splash10-00os-1092021000-dfd123715459896c106b	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 40V, Positive-QTOF	splash10-00mt-1290020000-6064c23505566aa5059f	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 10V, Negative-QTOF	splash10-01u1-7196106000-8d7ebe09b68b4da24a2e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 20V, Negative-QTOF	splash10-004i-9020000000-316de4578cc6c723846a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 40V, Negative-QTOF	splash10-004i-9010000000-673edd9596ecce23c64f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 10V, Positive-QTOF	splash10-014i-1031293000-5835d0fa74d0a96f2017	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 20V, Positive-QTOF	splash10-030a-9111583000-3ab27336202728521d55	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 40V, Positive-QTOF	splash10-0a4i-1985100000-406509471bc80dee7a37	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 10V, Negative-QTOF	splash10-03di-1000009000-7ebcbed37497909d70bf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 20V, Negative-QTOF	splash10-004j-9000001000-6ceb500438606d761db0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(O-16:0/18:0) 40V, Negative-QTOF	splash10-004j-9010000000-c1d1f1fe9603beb34469	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027920

KNApSAcK ID

Not Available

Chemspider ID

24766519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52929644

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 61 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Involved in protein binding
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:: PLD2
Uniprot ID:: O14939
Molecular weight:: 104656.485

Enzyme Details

2. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

3. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

Enzyme Details

4. Lipid phosphate phosphohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:: PPAP2C
Uniprot ID:: O43688
Molecular weight:: 32573.435

Enzyme Details

5. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

6. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

7. Lipid phosphate phosphohydrolase 1

General function:: Involved in catalytic activity
Specific function:: Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:: PPAP2A
Uniprot ID:: O14494
Molecular weight:: 32155.715

Enzyme Details

8. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

9. Diacylglycerol kinase iota

General function:: Involved in diacylglycerol kinase activity
Specific function:: ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:: DGKI
Uniprot ID:: O75912
Molecular weight:: 116996.2

Enzyme Details

10. Lipid phosphate phosphohydrolase 3

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:: PPAP2B
Uniprot ID:: O14495
Molecular weight:: 35115.61

Only showing the first 10 proteins. There are 61 proteins in total.

Show all enzymes and transporters

Showing metabocard for PA(O-16:0/18:0) (HMDB0011145)

MOL for HMDB0011145 (PA(O-16:0/18:0))

3D MOL for HMDB0011145 (PA(O-16:0/18:0))

3D SDF for HMDB0011145 (PA(O-16:0/18:0))

3D-SDF for HMDB0011145 (PA(O-16:0/18:0))

PDB for HMDB0011145 (PA(O-16:0/18:0))

3D PDB for HMDB0011145 (PA(O-16:0/18:0))

SMILES for HMDB0011145 (PA(O-16:0/18:0))

INCHI for HMDB0011145 (PA(O-16:0/18:0))

Structure for HMDB0011145 (PA(O-16:0/18:0))

3D Structure for HMDB0011145 (PA(O-16:0/18:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes