NP-MRD: Showing NP-Card for Ergocristam (NP0076516)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 21:41:33 UTC

Updated at

2022-04-28 21:41:33 UTC

NP-MRD ID

NP0076516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergocristam

Description

Ergocristam belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam. Ergocristam is found in Claviceps grohii. Ergocristam was first documented in 2008 (PMID: 18639312). Based on a literature review a small amount of articles have been published on Ergocristam (PMID: 18774762) (PMID: 18461998).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223412D          

 44 50  0  0  1  0            999 V2000
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5658    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237    2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6798    3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 17 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
  4 34  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 36 44  2  0  0  0  0
M  END

     RDKit          3D

 83 89  0  0  0  0  0  0  0  0999 V2000
    1.2659    0.1814   -3.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376    0.1531   -3.0205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4518    1.5260   -2.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -0.5417   -1.6943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7496   -0.4785   -0.8534 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505   -1.6257   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476   -2.7493   -0.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404   -1.5039    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8097   -0.9547   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6411   -0.1557    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8171    0.4132   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8857    0.4210   -1.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0371    0.9791   -2.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0636    1.5013   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9924    1.4926   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7534    1.8885    0.8213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1120    1.5927    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8805    0.9772    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8523    0.9382    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7563    0.4320    2.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4883    0.2454    1.7031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6216   -0.6755    2.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -1.9064    2.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727   -0.8110    1.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192    0.0988   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    1.1683   -0.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -0.2754   -0.8072 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.4674   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489   -2.0063   -2.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296   -2.0785   -0.7621 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3144   -2.9560   -1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7594   -2.9221   -1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9098   -1.6399   -0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -1.0267   -0.5957 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1663    0.3449   -0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544    1.2792   -0.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    0.5433   -0.0267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6616    0.3649    1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6396    1.2325    2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034    0.7820    2.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8309    1.6192    3.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4682    2.9187    3.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2045    3.3641    3.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3081    2.5218    2.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387   -0.7737   -4.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    0.9682   -4.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523    0.4152   -3.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -0.4577   -3.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2316    2.1864   -2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    1.9930   -3.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    1.4533   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575   -1.5926   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805    0.4587   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -2.5497    0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9379   -1.2380   -1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889    0.0199   -2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0978    0.9889   -3.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9311    1.9212   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6761    2.3442    0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4496    1.7788    2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0686   -0.5016    2.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735    1.1656    3.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9198    1.2220    1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436   -1.8862    3.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1963   -2.0184    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6602   -2.7985    2.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448    0.2010    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -1.4385    2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707   -2.5987    0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -2.4520   -2.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -3.9593   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9809   -3.8223   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4142   -2.8410   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1640   -1.9190    0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7066   -0.9790   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    1.6202   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7544   -0.6905    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    0.7174    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1891   -0.2307    2.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8318    1.3015    3.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2188    3.5475    3.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238    4.3640    3.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996    2.8756    2.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8 24  1  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 19  2  0
 11 10  1  0
 10  9  2  0
  4 25  1  0
 25 26  2  0
 25 27  1  0
 27 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 37 35  1  0
 35 36  2  0
 35 34  1  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
  9  8  1  0
 28 27  1  0
 10 21  1  0
 44 39  1  0
 30 34  1  0
 19 18  1  0
 19 15  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  6
  3 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  6
  5 53  1  0
  8 54  1  1
 24 67  1  0
 24 68  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 21 63  1  6
 20 61  1  0
 20 62  1  0
 17 60  1  0
 16 59  1  0
 14 58  1  0
 13 57  1  0
 12 56  1  0
  9 55  1  0
 37 76  1  1
 38 77  1  0
 38 78  1  0
 40 79  1  0
 41 80  1  0
 42 81  1  0
 43 82  1  0
 44 83  1  0
 33 74  1  0
 33 75  1  0
 32 72  1  0
 32 73  1  0
 31 70  1  0
 31 71  1  0
 30 69  1  1
M  END


  Mrv1652304282223412D          

 44 50  0  0  1  0            999 V2000
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5658    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237    2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6798    3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 17 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
  4 34  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 36 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0076516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H39N5O4/c1-20(2)31(35(44)40-29(15-21-9-5-4-6-10-21)33(42)39-14-8-13-27(39)34(40)43)37-32(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-28(25)38(3)19-23/h4-7,9-12,16,18,20,23,27-29,31,36H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28-,29+,31+/m1/s1

> <INCHI_KEY>
KMDKLWZQLMBIBS-HVWSGMRBSA-N

> <FORMULA>
C35H39N5O4

> <MOLECULAR_WEIGHT>
593.728

> <EXACT_MASS>
593.300204756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
64.35548574729845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.346373715666666

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.075343474805106

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.680791043104605

> <JCHEM_PKA_STRONGEST_BASIC>
7.956909273944205

> <JCHEM_POLAR_SURFACE_AREA>
105.82

> <JCHEM_REFRACTIVITY>
167.73999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      10.122   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.789   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.123  -0.770   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      12.789   1.540   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      14.123   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.123   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.456   4.620   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      12.789   4.620   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.122   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.311   4.880   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.937   6.287   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.469   6.126   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.456   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.790   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.790   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.124   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.457   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.457   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.124   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   38                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20                                                       
CONECT   27   17   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34    4                                                            
CONECT   35    3   36                                                       
CONECT   36   35   37   44                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37    2   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   36                                                       
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₉N₅O₄

Average Mass

593.7280 Da

Monoisotopic Mass

593.30020 Da

IUPAC Name

(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]2C1=O

InChI Identifier

InChI=1S/C35H39N5O4/c1-20(2)31(35(44)40-29(15-21-9-5-4-6-10-21)33(42)39-14-8-13-27(39)34(40)43)37-32(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-28(25)38(3)19-23/h4-7,9-12,16,18,20,23,27-29,31,36H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28-,29+,31+/m1/s1

InChI Key

KMDKLWZQLMBIBS-HVWSGMRBSA-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

Species Name	Source	Reference
Claviceps grohii	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergopeptams

Alternative Parents

Substituents

Ergopeptam-skeleton
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
N-acyl-alpha amino acid or derivatives
Quinoline-3-carboxamide
Pyrroloquinoline
Valine or derivatives
Alpha-amino acid amide
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Isoindole or derivatives
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Aralkylamine
N-alkylpiperazine
Piperazine
Carboxylic acid imide, n-substituted
1,4-diazinane
Monocyclic benzene moiety
Benzenoid
Carboxylic acid imide
Dicarboximide
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Lactam
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Amine
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.28	ALOGPS
logP	3.35	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	167.74 m³·mol⁻¹	ChemAxon
Polarizability	64.36 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039138

Chemspider ID

58828136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101428704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uhlig S, Petersen D: Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses. Toxicon. 2008 Jul;52(1):175-85. doi: 10.1016/j.toxicon.2008.05.002. Epub 2008 May 29. [PubMed:18639312 ]
Olsovska J, Sulc M, Novak P, Pazoutova S, Flieger M: Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Oct 1;873(2):165-72. doi: 10.1016/j.jchromb.2008.08.004. Epub 2008 Aug 15. [PubMed:18774762 ]
Pazoutova S, Olsovska J, Sulc M, Chudickova M, Flieger M: Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement. J Nat Prod. 2008 Jun;71(6):1085-8. doi: 10.1021/np8001173. Epub 2008 May 8. [PubMed:18461998 ]

Showing NP-Card for Ergocristam (NP0076516)

MOL for NP0076516 (Ergocristam)

3D MOL for NP0076516 (Ergocristam)

3D SDF for NP0076516 (Ergocristam)

3D-SDF for NP0076516 (Ergocristam)

PDB for NP0076516 (Ergocristam)

3D PDB for NP0076516 (Ergocristam)

SMILES for NP0076516 (Ergocristam)

INCHI for NP0076516 (Ergocristam)

Structure for NP0076516 (Ergocristam)

3D Structure for NP0076516 (Ergocristam)