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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 14:50:28 UTC

Update Date

2022-03-07 02:51:03 UTC

HMDB ID

HMDB0011152

Secondary Accession Numbers

HMDB11152

Metabolite Identification

Common Name

LysoPE(P-16:0/0:0)

Description

1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an phospho-ether lipid. 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. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.

Structure

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

  Mrv1652304202021112D          

 30 29  0  0  1  0            999 V2000
   21.5537   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8786   -6.4867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.2035   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2288   -6.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5283   -6.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3518   -7.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9039   -6.0969    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.5142   -5.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2937   -6.7720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5790   -5.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2541   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9292   -5.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6044   -6.0969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4663   -7.2960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8113   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0943   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3772   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6601   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9431   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2261   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5090   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8034   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0863   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6522   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9352   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2181   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5011   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7841   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0666   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
  5 15  1  0  0  0  0
M  END

HMDB0011152
     RDKit          3D
LysoPE(P-16:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
  -10.6209   -0.3732   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7493   -1.5876   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3171   -0.9994   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3585   -2.0879   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9999   -1.7019   -1.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1577   -0.8444   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320    0.5591   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    1.3656    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3180    1.5017    0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785    0.3016    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.5954    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.6454    1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    1.8584    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005    2.3074    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7960    2.4920    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618    1.8160   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    0.9095   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -0.3669   -1.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703   -1.3264   -0.7163 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0427   -2.5426   -1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.8947    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278   -0.7449   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.2667    0.4324 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7738    1.0212    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.4856    1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4687   -0.0546   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6740   -0.1859    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7963    0.0245   -0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0641   -0.1006   -0.2367 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6332   -0.6491    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0710    0.2495    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6347    0.2159   -0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7339   -2.2861    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0065   -2.0495   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4260   -0.2671   -1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1151   -0.5924    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -2.6928   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3250   -2.8193    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -2.6811   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9271   -1.3322   -2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9574   -1.3538    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572   -0.8232   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    1.0823   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072    0.8064    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0530    1.0137    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1853    2.4409    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739    2.3159    1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319    1.8954   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -0.6213    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    0.0669    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    0.9253   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604   -0.3688    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986    1.3549    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    2.6094    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    0.9121    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298    2.5841    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677    3.3326    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    1.6237   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2256    3.2071    0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.9930   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -0.2781   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -0.8008   -2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -1.5363   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -2.9798   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6691    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311    0.0389    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7511   -2.2816    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6839    0.6283    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7249   -1.1615    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7123    1.0705   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7099   -0.6781   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7524   -0.6090   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9489   -0.6703    0.6542 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  1
 20 64  1  0
 21 65  1  0
 21 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END

  Mrv1652304202021112D          

 30 29  0  0  1  0            999 V2000
   21.5537   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8786   -6.4867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.2035   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2288   -6.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5283   -6.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3518   -7.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9039   -6.0969    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.5142   -5.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2937   -6.7720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5790   -5.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2541   -6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9292   -5.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6044   -6.0969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4663   -7.2960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8113   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0943   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3772   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6601   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9431   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2261   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5090   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8034   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0863   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6522   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9352   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2181   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5011   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7841   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0666   -6.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
  5 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011152

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/b17-15-/t21-/m1/s1

> <INCHI_KEY>
QYTPGOPLNFESQC-NUTQULCTSA-N

> <FORMULA>
C21H44NO6P

> <MOLECULAR_WEIGHT>
437.5509

> <EXACT_MASS>
437.290624657

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.64536480940502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
3.922636067612286

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.662854416437519

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8690840302483096

> <JCHEM_PKA_STRONGEST_BASIC>
9.999834950611536

> <JCHEM_POLAR_SURFACE_AREA>
111.24

> <JCHEM_REFRACTIVITY>
117.75099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy((2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011152
     RDKit          3D
LysoPE(P-16:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
  -10.6209   -0.3732   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7493   -1.5876   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3171   -0.9994   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3585   -2.0879   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9999   -1.7019   -1.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1577   -0.8444   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320    0.5591   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    1.3656    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3180    1.5017    0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785    0.3016    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.5954    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.6454    1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    1.8584    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005    2.3074    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7960    2.4920    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618    1.8160   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    0.9095   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -0.3669   -1.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703   -1.3264   -0.7163 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0427   -2.5426   -1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.8947    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278   -0.7449   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.2667    0.4324 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7738    1.0212    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.4856    1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4687   -0.0546   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6740   -0.1859    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7963    0.0245   -0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0641   -0.1006   -0.2367 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6332   -0.6491    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0710    0.2495    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6347    0.2159   -0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7339   -2.2861    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0065   -2.0495   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4260   -0.2671   -1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1151   -0.5924    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -2.6928   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3250   -2.8193    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -2.6811   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9271   -1.3322   -2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9574   -1.3538    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572   -0.8232   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    1.0823   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072    0.8064    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0530    1.0137    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1853    2.4409    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739    2.3159    1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319    1.8954   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -0.6213    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    0.0669    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    0.9253   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604   -0.3688    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986    1.3549    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    2.6094    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    0.9121    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298    2.5841    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677    3.3326    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    1.6237   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2256    3.2071    0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.9930   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -0.2781   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -0.8008   -2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -1.5363   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -2.9798   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6691    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311    0.0389    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7511   -2.2816    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6839    0.6283    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7249   -1.1615    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7123    1.0705   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7099   -0.6781   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7524   -0.6090   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9489   -0.6703    0.6542 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  1
 20 64  1  0
 21 65  1  0
 21 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      40.234 -11.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      38.973 -12.109   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.713 -11.381   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      41.494 -12.109   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      36.453 -12.109   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.990 -13.564   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      42.754 -11.381   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      42.027 -10.121   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      43.482 -12.641   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      44.014 -10.653   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      45.274 -11.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.535 -10.653   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      47.795 -11.381   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      40.070 -13.619   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      35.114 -11.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.776 -11.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.437 -12.109   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.099 -11.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.760 -12.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.422 -11.347   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.083 -12.109   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.766 -11.347   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.428 -12.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.089 -11.347   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.751 -12.109   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.412 -11.347   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.074 -12.109   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.735 -11.347   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.397 -12.109   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.058 -11.347   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   15                                                       
CONECT    6    2                                                            
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
CONECT   15   16    5                                                       
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   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0011152
HETATM    1  C1  UNL     1     -10.621  -0.373  -0.004  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.749  -1.588  -0.247  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.317  -0.999  -0.484  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.359  -2.088  -0.735  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.000  -1.702  -1.086  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.158  -0.844  -0.212  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.532   0.559  -0.021  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.780   1.366   0.974  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.318   1.502   0.848  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.478   0.302   1.092  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.985   0.595   0.898  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.460   1.645   1.815  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.999   1.858   1.600  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.300   2.307   0.196  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.796   2.492   0.145  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.562   1.816  -0.682  1.00  0.00           C  
HETATM   17  O1  UNL     1       3.020   0.910  -1.536  1.00  0.00           O  
HETATM   18  C17 UNL     1       3.473  -0.367  -1.855  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.570  -1.326  -0.716  1.00  0.00           C  
HETATM   20  O2  UNL     1       4.043  -2.543  -1.261  1.00  0.00           O  
HETATM   21  C19 UNL     1       4.673  -0.895   0.257  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.828  -0.745  -0.511  1.00  0.00           O  
HETATM   23  P1  UNL     1       7.143  -0.267   0.432  1.00  0.00           P  
HETATM   24  O4  UNL     1       6.774   1.021   1.140  1.00  0.00           O  
HETATM   25  O5  UNL     1       7.419  -1.486   1.582  1.00  0.00           O  
HETATM   26  O6  UNL     1       8.469  -0.055  -0.583  1.00  0.00           O  
HETATM   27  C20 UNL     1       9.674  -0.186   0.111  1.00  0.00           C  
HETATM   28  C21 UNL     1      10.796   0.024  -0.901  1.00  0.00           C  
HETATM   29  N1  UNL     1      12.064  -0.101  -0.237  1.00  0.00           N  
HETATM   30  H1  UNL     1     -11.633  -0.649   0.344  1.00  0.00           H  
HETATM   31  H2  UNL     1     -10.071   0.250   0.753  1.00  0.00           H  
HETATM   32  H3  UNL     1     -10.635   0.216  -0.936  1.00  0.00           H  
HETATM   33  H4  UNL     1      -9.734  -2.286   0.591  1.00  0.00           H  
HETATM   34  H5  UNL     1     -10.006  -2.049  -1.218  1.00  0.00           H  
HETATM   35  H6  UNL     1      -8.426  -0.267  -1.267  1.00  0.00           H  
HETATM   36  H7  UNL     1      -8.115  -0.592   0.548  1.00  0.00           H  
HETATM   37  H8  UNL     1      -7.797  -2.693  -1.611  1.00  0.00           H  
HETATM   38  H9  UNL     1      -7.325  -2.819   0.144  1.00  0.00           H  
HETATM   39  H10 UNL     1      -5.400  -2.681  -1.187  1.00  0.00           H  
HETATM   40  H11 UNL     1      -5.927  -1.332  -2.176  1.00  0.00           H  
HETATM   41  H12 UNL     1      -4.957  -1.354   0.733  1.00  0.00           H  
HETATM   42  H13 UNL     1      -4.157  -0.823  -0.836  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.335   1.082  -1.063  1.00  0.00           H  
HETATM   44  H15 UNL     1      -6.607   0.806   0.093  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.053   1.014   2.035  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.185   2.441   0.994  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.974   2.316   1.560  1.00  0.00           H  
HETATM   48  H19 UNL     1      -3.132   1.895  -0.214  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.677  -0.621   0.602  1.00  0.00           H  
HETATM   50  H21 UNL     1      -2.598   0.067   2.213  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.830   0.925  -0.167  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.460  -0.369   1.011  1.00  0.00           H  
HETATM   53  H24 UNL     1      -0.599   1.355   2.886  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.027   2.609   1.675  1.00  0.00           H  
HETATM   55  H26 UNL     1       1.584   0.912   1.785  1.00  0.00           H  
HETATM   56  H27 UNL     1       1.430   2.584   2.342  1.00  0.00           H  
HETATM   57  H28 UNL     1       0.868   3.333   0.069  1.00  0.00           H  
HETATM   58  H29 UNL     1       0.973   1.624  -0.586  1.00  0.00           H  
HETATM   59  H30 UNL     1       3.226   3.207   0.819  1.00  0.00           H  
HETATM   60  H31 UNL     1       4.619   1.993  -0.669  1.00  0.00           H  
HETATM   61  H32 UNL     1       4.489  -0.278  -2.310  1.00  0.00           H  
HETATM   62  H33 UNL     1       2.787  -0.801  -2.618  1.00  0.00           H  
HETATM   63  H34 UNL     1       2.629  -1.536  -0.211  1.00  0.00           H  
HETATM   64  H35 UNL     1       4.690  -2.980  -0.675  1.00  0.00           H  
HETATM   65  H36 UNL     1       4.806  -1.669   1.047  1.00  0.00           H  
HETATM   66  H37 UNL     1       4.431   0.039   0.779  1.00  0.00           H  
HETATM   67  H38 UNL     1       7.751  -2.282   1.113  1.00  0.00           H  
HETATM   68  H39 UNL     1       9.684   0.628   0.864  1.00  0.00           H  
HETATM   69  H40 UNL     1       9.725  -1.161   0.602  1.00  0.00           H  
HETATM   70  H41 UNL     1      10.712   1.070  -1.267  1.00  0.00           H  
HETATM   71  H42 UNL     1      10.710  -0.678  -1.747  1.00  0.00           H  
HETATM   72  H43 UNL     1      12.752  -0.609  -0.861  1.00  0.00           H  
HETATM   73  H44 UNL     1      11.949  -0.670   0.654  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   47   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   53   54
CONECT   13   14   55   56
CONECT   14   15   57   58
CONECT   15   16   16   59
CONECT   16   17   60
CONECT   17   18
CONECT   18   19   61   62
CONECT   19   20   21   63
CONECT   20   64
CONECT   21   22   65   66
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   67
CONECT   26   27
CONECT   27   28   68   69
CONECT   28   29   70   71
CONECT   29   72   73
END

HMDB0011152
     RDKit          3D
LysoPE(P-16:0/0:0)
 73 72  0  0  0  0  0  0  0  0999 V2000
  -10.6209   -0.3732   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7493   -1.5876   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3171   -0.9994   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3585   -2.0879   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9999   -1.7019   -1.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1577   -0.8444   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320    0.5591   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    1.3656    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3180    1.5017    0.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785    0.3016    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.5954    0.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.6454    1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    1.8584    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005    2.3074    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7960    2.4920    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618    1.8160   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    0.9095   -1.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -0.3669   -1.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703   -1.3264   -0.7163 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0427   -2.5426   -1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.8947    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278   -0.7449   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.2667    0.4324 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7738    1.0212    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.4856    1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4687   -0.0546   -0.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6740   -0.1859    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7963    0.0245   -0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0641   -0.1006   -0.2367 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6332   -0.6491    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0710    0.2495    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6347    0.2159   -0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7339   -2.2861    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0065   -2.0495   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4260   -0.2671   -1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1151   -0.5924    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7967   -2.6928   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3250   -2.8193    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -2.6811   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9271   -1.3322   -2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9574   -1.3538    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572   -0.8232   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    1.0823   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072    0.8064    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0530    1.0137    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1853    2.4409    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739    2.3159    1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319    1.8954   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -0.6213    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    0.0669    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    0.9253   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604   -0.3688    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986    1.3549    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    2.6094    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    0.9121    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298    2.5841    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677    3.3326    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    1.6237   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2256    3.2071    0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6194    1.9930   -0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -0.2781   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -0.8008   -2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -1.5363   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -2.9798   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -1.6691    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311    0.0389    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7511   -2.2816    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6839    0.6283    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7249   -1.1615    0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7123    1.0705   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7099   -0.6781   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7524   -0.6090   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9489   -0.6703    0.6542 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  1
 20 64  1  0
 21 65  1  0
 21 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(1Z-Hexadecenyl)-lysophosphatidylethanolamine	HMDB
1-(1Z-Hexadecenyl)-sn-glycero-3-phosphoethanolamine	HMDB
LPE(16:1)	HMDB
LPE(p-16:0)	HMDB
LPE(p-16:0/0:0)	HMDB
Lysophosphatidylethanolamine(16:1)	HMDB
Lysophosphatidylethanolamine(p-16:0)	HMDB
Lysophosphatidylethanolamine(p-16:0/0:0)	HMDB
LysoPE(16:1)	HMDB
LysoPE(p-16:0)	HMDB
LysoPE(O-16:1(1Z))	HMDB
LysoPE(O-16:1(1Z)/0:0)	HMDB
1-(1Z-Hexadecenyl)-gpe	HMDB
GPE(16:1)	HMDB
GPE(O-16:1(1Z))	HMDB
GPE(O-16:1(1Z)/0:0)	HMDB
GPE(p-16:0)	HMDB
GPE(p-16:0/0:0)	HMDB
LPE(O-16:1(1Z))	HMDB
LPE(O-16:1(1Z)/0:0)	HMDB
Lysophosphatidylethanolamine(O-16:1(1Z))	HMDB
Lysophosphatidylethanolamine(O-16:1(1Z)/0:0)	HMDB
1-(1-Enyl-palmitoyl)-gpe	HMDB
LysoPE(P-16:0/0:0)	HMDB

Chemical Formula

C₂₁H₄₄NO₆P

Average Molecular Weight

437.5509

Monoisotopic Molecular Weight

437.290624657

IUPAC Name

(2-aminoethoxy)[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy]phosphinic acid

Traditional Name

2-aminoethoxy((2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy)phosphinic acid

CAS Registry Number

174062-72-7

SMILES

[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN

InChI Identifier

InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/b17-15-/t21-/m1/s1

InChI Key

QYTPGOPLNFESQC-NUTQULCTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphoethanolamines. These are glycerophosphoglycerophosphates that carry exactly one 1Z-alkenyl chain attached to the glycerol moiety through an ether linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

1-(1Z-alkenyl)-glycero-3-phosphoethanolamines

Alternative Parents

Substituents

1-(1z-alkenyl)-glycero-3-phosphoethanolamine
Glycerol vinyl ether
Phosphoethanolamine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1Z-alkenylglycerophosphoethanolamines (LMGP02070001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22685041)

Organ

Placenta (HMDB: HMDB0011152)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Extracellular (HMDB: HMDB0011152)
Membrane (HMDB: HMDB0011152)

Source

Exogenous

Exogenous (HMDB: HMDB0011152)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0011152)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	4.63	ALOGPS
logP	3.92	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.24 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	117.75 m³·mol⁻¹	ChemAxon
Polarizability	50.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	212.611	31661259
DarkChem	[M-H]-	206.072	31661259
DeepCCS	[M+H]+	187.312	30932474
DeepCCS	[M-H]-	184.386	30932474
DeepCCS	[M-2H]-	220.222	30932474
DeepCCS	[M+Na]+	194.999	30932474
AllCCS	[M+H]+	212.1	32859911
AllCCS	[M+H-H2O]+	210.2	32859911
AllCCS	[M+NH4]+	213.8	32859911
AllCCS	[M+Na]+	214.3	32859911
AllCCS	[M-H]-	208.5	32859911
AllCCS	[M+Na-2H]-	210.8	32859911
AllCCS	[M+HCOO]-	213.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPE(P-16:0/0:0)	[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN	3633.2	Standard polar	33892256
LysoPE(P-16:0/0:0)	[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN	2973.9	Standard non polar	33892256
LysoPE(P-16:0/0:0)	[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCC)COP(O)(=O)OCCN	3334.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPE(P-16:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN)O[Si](C)(C)C	3293.0	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),1TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN)O[Si](C)(C)C	3269.4	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),1TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN[Si](C)(C)C	3380.6	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	3269.2	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	3044.3	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	4338.3	Standard polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	3341.3	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	3200.7	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	4351.3	Standard polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	3322.3	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	3222.0	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	3844.0	Standard polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	3525.0	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	3253.3	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	4412.2	Standard polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3305.9	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3208.5	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3551.8	Standard polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3496.6	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3257.4	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	4078.2	Standard polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3503.1	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3277.7	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3676.7	Standard polar	33892256
LysoPE(P-16:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3491.8	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3250.6	Standard non polar	33892256
LysoPE(P-16:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3420.9	Standard polar	33892256
LysoPE(P-16:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN)O[Si](C)(C)C(C)(C)C	3514.5	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),1TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C	3466.8	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),1TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C	3595.6	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3682.0	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3295.8	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4296.9	Standard polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3770.8	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3475.0	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4296.5	Standard polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3760.2	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3477.2	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3917.9	Standard polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3963.9	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3521.3	Standard non polar	33892256
LysoPE(P-16:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4346.9	Standard polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3967.9	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3593.1	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3705.1	Standard polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4225.9	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3662.0	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4057.7	Standard polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4173.2	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3656.6	Standard non polar	33892256
LysoPE(P-16:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCC/C=C\OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3788.7	Standard polar	33892256
LysoPE(P-16:0/0:0),4TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4405.5	Semi standard non polar	33892256
LysoPE(P-16:0/0:0),4TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3753.1	Standard non polar	33892256
LysoPE(P-16:0/0:0),4TBDMS,isomer #1	CCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3634.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPE(P-16:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-4911100000-d1601c2704b1a1e118ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPE(P-16:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0it9-7491200000-2eb4e80e5df4cef2110d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPE(P-16:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 10V, Positive-QTOF	splash10-0006-9020200000-e163fc5a1ee5330da77d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 20V, Positive-QTOF	splash10-0006-9120000000-fe3ce0f563cf0b8c447a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 40V, Positive-QTOF	splash10-0006-9130000000-e797e3149b9f3935a2a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 10V, Negative-QTOF	splash10-000i-3485900000-e3410801ae2e61ac63ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 20V, Negative-QTOF	splash10-004l-9541000000-76579d705c9a17b33cff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 40V, Negative-QTOF	splash10-01t9-9000000000-c2853fc10de5a9dc0647	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 10V, Negative-QTOF	splash10-000i-0000900000-d8db21ed47b93cb4b7a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 20V, Negative-QTOF	splash10-000i-0111900000-929406e3ce92241cadcf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(P-16:0/0:0) 40V, Negative-QTOF	splash10-000i-0000900000-d8db21ed47b93cb4b7a1	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22685041	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Kidney cancer	22685041	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Kidney cancer
Lin L, Huang Z, Gao Y, Chen Y, Hang W, Xing J, Yan X: LC-MS-based serum metabolic profiling for genitourinary cancer classification and cancer type-specific biomarker discovery. Proteomics. 2012 Aug;12(14):2238-46. doi: 10.1002/pmic.201200016. [PubMed:22685041 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027927

KNApSAcK ID

Not Available

Chemspider ID

24769219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607469

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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 30 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

References

Enzyme Details

2. Phospholipase D1

General function:: Involved in protein binding
Specific function:: Implicated as a critical step in numerous cellular pathways, including signal transduction, membrane trafficking, and the regulation of mitosis. May be involved in the regulation of perinuclear intravesicular membrane traffic (By similarity).
Gene Name:: PLD1
Uniprot ID:: Q13393
Molecular weight:: 124183.135

References

Enzyme Details

3. Probable phospholipid-transporting ATPase IG

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP11C
Uniprot ID:: Q8NB49
Molecular weight:: 129476.0

References

Enzyme Details

4. Probable phospholipid-transporting ATPase IH

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP11A
Uniprot ID:: P98196
Molecular weight:: 129754.6

References

Enzyme Details

5. Probable phospholipid-transporting ATPase VA

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP10A
Uniprot ID:: O60312
Molecular weight:: 167686.6

References

Enzyme Details

6. Probable phospholipid-transporting ATPase IC

General function:: Involved in ATP binding
Specific function:: May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids in the canicular membrane. May have a role in transport of bile acids into the canaliculus, uptake of bile acids from intestinal contents into intestinal mucosa or both
Gene Name:: ATP8B1
Uniprot ID:: O43520
Molecular weight:: 143694.1

References

Enzyme Details

7. Probable phospholipid-transporting ATPase IIA

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP9A
Uniprot ID:: O75110
Molecular weight:: 118581.5

References

Enzyme Details

8. Probable phospholipid-transporting ATPase VD

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP10D
Uniprot ID:: Q9P241
Molecular weight:: 160272.3

References

Enzyme Details

9. Probable phospholipid-transporting ATPase IB

General function:: Involved in ATP binding
Specific function:: ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:: ATP8A2
Uniprot ID:: Q9NTI2
Molecular weight:: 129240.4

References

Enzyme Details

10. Probable phospholipid-transporting ATPase IA

General function:: Involved in ATP binding
Specific function:: May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:: ATP8A1
Uniprot ID:: Q9Y2Q0
Molecular weight:: 131368.2

References

Only showing the first 10 proteins. There are 30 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPE(P-16:0/0:0) (HMDB0011152)

MOL for HMDB0011152 (LysoPE(P-16:0/0:0))

3D MOL for HMDB0011152 (LysoPE(P-16:0/0:0))

3D SDF for HMDB0011152 (LysoPE(P-16:0/0:0))

3D-SDF for HMDB0011152 (LysoPE(P-16:0/0:0))

PDB for HMDB0011152 (LysoPE(P-16:0/0:0))

3D PDB for HMDB0011152 (LysoPE(P-16:0/0:0))

SMILES for HMDB0011152 (LysoPE(P-16:0/0:0))

INCHI for HMDB0011152 (LysoPE(P-16:0/0:0))

Structure for HMDB0011152 (LysoPE(P-16:0/0:0))

3D Structure for HMDB0011152 (LysoPE(P-16:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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