NP-MRD: Showing NP-Card for LysoPE(P-16:0/0:0) (NP0136831)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:24:46 UTC

Updated at

2022-05-12 15:24:46 UTC

NP-MRD ID

NP0136831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

LysoPE(P-16:0/0:0), Also known as lpe(16:1) Or lpe(p-16:0/0:0), 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. Thus, lysope(p-16:0/0:0) Is considered to be a glycerophosphoethanolamine lipid molecule. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. LysoPE(P-16:0/0:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 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. 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. 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. Plasmalogens are glycerol ether phospholipids. Ethanolamine plasmalogen is prevalent in myelin. Three major classes of plasmalogens have been identified: Choline, ethanolamine and serine derivatives. PE synthesis can occur via two pathways.

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 73 72  0  0  0  0  0  0  0  0999 V2000
   10.3842    0.8506    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1672   -0.6447    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6722   -0.8658    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9139   -0.5794   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4206   -0.7707   -0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364    0.3193    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5843    1.6058   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3366    1.6497   -0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181    1.3039   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -0.1111    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789   -0.6210    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5479   -0.2846    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091   -1.0339    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3319   -0.3085   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111    0.8124    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4095    0.3308    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090   -1.0212    0.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2031   -1.5711   -0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4520   -0.9122   -0.7455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2292    0.5506   -0.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5209   -0.9836   -1.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5485   -0.4287   -1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1431    1.1126   -1.5138 P   0  0  2  0  0  5  0  0  0  0  0  0
   -7.8889    1.6538   -2.7928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6693    2.1778   -0.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8536    0.7549   -1.1672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6621    0.5320    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5877   -0.5425    0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4799   -0.7749    2.1017 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4692    1.3857    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5606    1.1295   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2288    1.1953    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5966   -1.2329   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068   -0.8692    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2025   -0.5032    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5989   -2.0242    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1026    0.3772   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541   -1.3924   -1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715   -1.7356    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -0.8387   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9351    0.6333    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228    0.0516    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968    2.4211    0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4605    1.8979   -0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595    2.5426   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4047    0.8159   -1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240    1.4569   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    2.0390    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    0.0422    1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -0.7862   -0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -0.4806   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970   -1.7829    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2900    0.7423    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7593   -0.8585    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -1.2550    1.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856   -1.9933    0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087    0.3550   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -0.8094   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684    1.8194    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    1.0602    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5883   -1.4594   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2881   -2.6859   -0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9738   -1.0998    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7717    0.7031   -1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7459   -2.1229   -1.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063   -0.6674   -2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873    2.7122   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2249    1.5007    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7020    0.6473    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5104   -0.5956    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0550   -1.5495    0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8787   -0.0480    2.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4469   -0.9384    2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 19 21  1  0
 21 22  1  0
 23 22  1  1
 23 25  1  0
 23 24  2  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 19 63  1  1
 20 64  1  0
 18 61  1  0
 18 62  1  0
 16 60  1  0
 15 59  1  0
 14 57  1  0
 14 58  1  0
 13 55  1  0
 13 56  1  0
 12 53  1  0
 12 54  1  0
 11 51  1  0
 11 52  1  0
 10 49  1  0
 10 50  1  0
  9 47  1  0
  9 48  1  0
  8 45  1  0
  8 46  1  0
  7 43  1  0
  7 44  1  0
  6 41  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  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>
NP0136831

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

437.5509 Da

Monoisotopic Mass

437.29062 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	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

External Links

HMDB ID

HMDB0011152

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Showing NP-Card for LysoPE(P-16:0/0:0) (NP0136831)

MOL for NP0136831 (LysoPE(P-16:0/0:0))

3D MOL for NP0136831 (LysoPE(P-16:0/0:0))

3D SDF for NP0136831 (LysoPE(P-16:0/0:0))

3D-SDF for NP0136831 (LysoPE(P-16:0/0:0))

PDB for NP0136831 (LysoPE(P-16:0/0:0))

3D PDB for NP0136831 (LysoPE(P-16:0/0:0))

SMILES for NP0136831 (LysoPE(P-16:0/0:0))

INCHI for NP0136831 (LysoPE(P-16:0/0:0))

Structure for NP0136831 (LysoPE(P-16:0/0:0))

3D Structure for NP0136831 (LysoPE(P-16:0/0:0))