NP-MRD: Showing NP-Card for (2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide (NP0148752)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 04:32:51 UTC

Updated at

2022-09-02 04:32:51 UTC

NP-MRD ID

NP0148752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide

Description

Dimerum acid belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide was first documented in 2013 (PMID: 23064341). Based on a literature review a small amount of articles have been published on Dimerum acid (PMID: 32402399) (PMID: 26183915).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206322D          

 34 34  0  0  0  0            999 V2000
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 70 70  0  0  0  0  0  0  0  0999 V2000
   -6.5373    1.4155   -0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2196    1.8269    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4857    1.0538    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465   -0.2264    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1695   -0.6646   -0.4319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1726   -0.9792    1.6353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670   -0.5243    2.8838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -2.2188    1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1700   -2.1025    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261   -1.2430   -0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246   -1.0992   -1.0726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2598   -2.4171   -1.4265 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -3.1177   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -4.3762   -1.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034   -2.5746    0.5231 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5965   -2.8907    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2518   -2.2259   -0.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368   -2.5210   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.9008   -1.5779 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -2.6110   -2.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8305   -0.5825   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3925   -0.1031   -2.5471 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    0.2013   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1124    1.4624   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854    2.0912   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9233    2.1943    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801    3.4342    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142    4.3602    0.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0163   -1.1198    0.5492 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.4438   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601    0.9631   -0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7524    3.1351    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2692    3.0563    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8260    4.2543    1.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1199    0.4720   -0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5862    1.3199   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1465    2.1971   -1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2730    1.3932    2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8018   -0.4308    3.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -2.9831    2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2679   -2.6459    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -3.1423    0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -1.7239    1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -0.2402   -0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132   -1.6728   -1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -0.5483   -2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468   -4.4981   -2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -2.9696    1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -2.4001    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -3.9683    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.1391   -0.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486   -2.6129   -1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9212   -3.6252   -0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1695   -2.1264    0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8697   -3.3421   -2.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1935   -0.1628    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1120    2.1859   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7114    1.5110   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1429    3.1094   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9553    2.4460    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603    1.5631    1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    3.1096    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    3.9115    1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3638    4.8483    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0737    1.4441    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4243    3.3629    1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4158    3.9117    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6616    2.2527    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5989    2.8739   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0076    4.8134    0.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 32  1  0
 32 33  1  0
 33 34  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 15 29  1  0
 29 30  2  0
 30 31  1  0
 30 11  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
 34 70  1  0
  3 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  6
 14 47  1  0
 15 48  1  1
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 20 55  1  0
 23 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 31 65  1  0
M  END


  Mrv1652309022206322D          

 34 34  0  0  0  0            999 V2000
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCO)=C/C(=O)N(O)CCCC1N=C(O)C(CCCN(O)C(=O)\C=C(/C)CCO)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36N4O8/c1-15(7-11-27)13-19(29)25(33)9-3-5-17-21(31)24-18(22(32)23-17)6-4-10-26(34)20(30)14-16(2)8-12-28/h13-14,17-18,27-28,33-34H,3-12H2,1-2H3,(H,23,32)(H,24,31)/b15-13+,16-14+

> <INCHI_KEY>
MKDKGLNKTMDNHY-WXUKJITCSA-N

> <FORMULA>
C22H36N4O8

> <MOLECULAR_WEIGHT>
484.55

> <EXACT_MASS>
484.253314135

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.76719033329823

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-[3-(5-{3-[(2E)-N,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-N,5-dihydroxy-3-methylpent-2-enamide

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-1.9592103983805718

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.146410948383469

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1960166642928742

> <JCHEM_PKA_STRONGEST_BASIC>
5.2930889058794035

> <JCHEM_POLAR_SURFACE_AREA>
186.71999999999997

> <JCHEM_REFRACTIVITY>
125.74319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[3-(5-{3-[(2E)-N,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-N,5-dihydroxy-3-methylpent-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.667   3.080   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.335   3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   15   30                                                       
CONECT   30   29   11   31                                                  
CONECT   31   30                                                            
CONECT   32    2   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
Dimerunic acid	MeSH

Chemical Formula

C₂₂H₃₆N₄O₈

Average Mass

484.5500 Da

Monoisotopic Mass

484.25331 Da

IUPAC Name

(2E)-N-[3-(5-{3-[(2E)-N,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-N,5-dihydroxy-3-methylpent-2-enamide

Traditional Name

(2E)-N-[3-(5-{3-[(2E)-N,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-N,5-dihydroxy-3-methylpent-2-enamide

CAS Registry Number

Not Available

SMILES

C\C(CCO)=C/C(=O)N(O)CCCC1N=C(O)C(CCCN(O)C(=O)\C=C(/C)CCO)N=C1O

InChI Identifier

InChI=1S/C22H36N4O8/c1-15(7-11-27)13-19(29)25(33)9-3-5-17-21(31)24-18(22(32)23-17)6-4-10-26(34)20(30)14-16(2)8-12-28/h13-14,17-18,27-28,33-34H,3-12H2,1-2H3,(H,23,32)(H,24,31)/b15-13+,16-14+

InChI Key

MKDKGLNKTMDNHY-WXUKJITCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
1,4-diazinane
Piperazine
Carboxamide group
Hydroxamic acid
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.18	ALOGPS
logP	-2	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	5.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.72 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	125.74 m³·mol⁻¹	ChemAxon
Polarizability	50.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4947731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang ZH, Liang X, Qi SH: A new iron(III) chelator of coprogen-type siderophore from the deep-sea-derived fungus Mycosphaerella sp. SCSIO z059. Chin J Nat Med. 2020 Apr;18(4):243-249. doi: 10.1016/S1875-5364(20)30029-7. [PubMed:32402399 ]
Arias AA, Lambert S, Martinet L, Adam D, Tenconi E, Hayette MP, Ongena M, Rigali S: Growth of desferrioxamine-deficient Streptomyces mutants through xenosiderophore piracy of airborne fungal contaminations. FEMS Microbiol Ecol. 2015 Jul;91(7):fiv080. doi: 10.1093/femsec/fiv080. Epub 2015 Jul 15. [PubMed:26183915 ]
Lehner SM, Atanasova L, Neumann NK, Krska R, Lemmens M, Druzhinina IS, Schuhmacher R: Isotope-assisted screening for iron-containing metabolites reveals a high degree of diversity among known and unknown siderophores produced by Trichoderma spp. Appl Environ Microbiol. 2013 Jan;79(1):18-31. doi: 10.1128/AEM.02339-12. Epub 2012 Oct 12. [PubMed:23064341 ]
LOTUS database [Link]

Showing NP-Card for (2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide (NP0148752)

MOL for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

3D MOL for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

3D SDF for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

3D-SDF for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

PDB for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

3D PDB for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

SMILES for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

INCHI for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

Structure for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)

3D Structure for NP0148752 ((2e)-n-[3-(5-{3-[(2e)-n,5-dihydroxy-3-methylpent-2-enamido]propyl}-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)propyl]-n,5-dihydroxy-3-methylpent-2-enamide)