NP-MRD: Showing NP-Card for n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0147454)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 03:03:55 UTC

Updated at

2022-09-02 03:03:55 UTC

NP-MRD ID

NP0147454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

Description

Ergocryptine belongs to the class of organic compounds known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Ergocryptine is a very strong basic compound (based on its pKa). Ergocryptine is a potentially toxic compound. Ergocryptine is an alkaloid of the ergoline family. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. As well as seizures there can be hallucinations and mental effects including mania or psychosis. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid is found in Claviceps purpurea and Claviceps zizaniae. Ergometrine is also known to have a non-receptor specific oxytocic activity.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212302D          

 42 48  0  0  0  0            999 V2000
    1.0554   -8.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -8.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735   -8.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -7.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -6.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -7.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918   -8.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -6.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -7.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0910   -6.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -5.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -6.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -5.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -6.0019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -5.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200   -5.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310   -4.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -4.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -4.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589   -3.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976   -4.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -3.8687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -5.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  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  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 30 38  1  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 40  1  0  0  0  0
 27 41  1  0  0  0  0
 13 42  1  0  0  0  0
M  END

     RDKit          3D

 83 89  0  0  0  0  0  0  0  0999 V2000
   -3.2670   -3.9340    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -2.9214   -0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4645   -2.9173   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2746   -1.6470   -0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542   -0.4548   -1.4275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0431   -0.0002   -1.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9781   -0.5043   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3681    1.0278   -0.3026 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    1.2638    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3658    2.6740    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8625    2.7992    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4062    2.0665   -0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0409    1.4252    0.1069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1006    0.6519    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    2.4096    0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985    2.0966   -0.5950 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1007    1.5119    0.1243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504    1.0631   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.1212   -1.7818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543    0.4743    0.2469 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5104    0.0647   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4671   -0.5850    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6444   -1.0316   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598   -0.7188   -2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0201   -1.2234   -2.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9321   -2.0006   -1.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6973   -2.3023   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3158   -2.9885    0.4376 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5314   -2.8949    1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4099   -2.1407    1.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -1.7897   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594   -1.7358    2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -0.8241    1.4558 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9551   -1.3525    1.7609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -1.3011    3.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164   -0.7682    0.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837    3.3585   -1.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737    4.0536   -2.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698    4.2966   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181    1.1176   -1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    0.7570   -2.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350    0.6362   -1.0269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607   -4.9642   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -3.7408    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1928   -3.6757    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9013   -3.3296   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6221   -3.8694    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1006   -3.1031   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7749   -2.1244    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2811   -1.4300    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -1.9088   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4594   -0.5733   -2.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034    0.5870    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4307    1.2602   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7606    3.4461    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8575    2.8042    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5310    3.8567    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    2.2472    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    2.7098   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3868    0.8572    1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350    1.4235    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7748    1.1822    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    0.2801   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872   -0.1383   -2.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2889   -1.0430   -3.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8324   -2.3810   -2.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2123   -3.4762    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7627   -3.3436    2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7947   -2.6419    2.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218   -1.1817    2.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2876    0.1991    1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4436   -0.7237    3.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674   -0.8668    3.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6080   -2.3568    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -1.5549    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -0.5212    1.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3112    3.1125   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    3.2687   -2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639    4.8037   -1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    4.5552   -2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    4.8577    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596    4.9630   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725    3.7015    0.7421 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 42  1  0
 42 40  1  0
 40 41  2  0
 40 16  1  0
 16 17  1  1
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 36  1  0
 36 34  1  0
 34 35  1  0
 34 33  1  0
 33 32  1  0
 32 30  1  0
 30 29  2  0
 29 28  1  0
 28 27  1  0
 27 26  2  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 31  2  0
 23 22  1  0
 22 21  2  0
 16 15  1  0
 15 13  1  0
 13 14  1  1
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
 16 37  1  0
 37 38  1  0
 37 39  1  0
  6  5  1  0
 13 42  1  0
  8 12  1  0
 21 20  1  0
 22 33  1  0
 31 30  1  0
 31 27  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  3 47  1  0
  3 48  1  0
  3 49  1  0
  4 50  1  0
  4 51  1  0
  5 52  1  6
 17 61  1  0
 20 62  1  1
 36 75  1  0
 36 76  1  0
 35 72  1  0
 35 73  1  0
 35 74  1  0
 33 71  1  1
 32 69  1  0
 32 70  1  0
 29 68  1  0
 28 67  1  0
 26 66  1  0
 25 65  1  0
 24 64  1  0
 21 63  1  0
 14 60  1  0
 12 59  1  6
 11 57  1  0
 11 58  1  0
 10 55  1  0
 10 56  1  0
  9 53  1  0
  9 54  1  0
 37 77  1  0
 38 78  1  0
 38 79  1  0
 38 80  1  0
 39 81  1  0
 39 82  1  0
 39 83  1  0
M  END


  Mrv0541 02241212302D          

 42 48  0  0  0  0            999 V2000
    1.0554   -8.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -8.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735   -8.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -7.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -6.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -7.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918   -8.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -6.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -7.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0910   -6.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -5.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -6.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -5.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -6.0019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -5.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200   -5.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310   -4.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -4.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -4.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589   -3.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976   -4.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -3.8687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -5.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  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  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 30 38  1  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 40  1  0  0  0  0
 27 41  1  0  0  0  0
 13 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC1N2C(=O)C(NC(=O)C3CN(C)C4CC5=CNC6=CC=CC(=C56)C4=C3)(OC2(O)C2CCCN2C1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)

> <INCHI_KEY>
YDOTUXAWKBPQJW-UHFFFAOYSA-N

> <FORMULA>
C32H41N5O5

> <MOLECULAR_WEIGHT>
575.6984

> <EXACT_MASS>
575.310769447

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
61.175277896085085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.311811306739158

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.711893609776439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.6959932809536

> <JCHEM_PKA_STRONGEST_BASIC>
7.780497513320139

> <JCHEM_POLAR_SURFACE_AREA>
118.21000000000002

> <JCHEM_REFRACTIVITY>
158.1076

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ergocryptine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.970 -15.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.629 -15.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.697 -15.823   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.615 -13.501   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.726 -12.744   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.052 -13.526   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.038 -15.066   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -3.393 -12.768   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.853 -13.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.770 -12.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.876 -10.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.407 -11.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.081 -10.446   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.740 -11.204   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.395 -10.163   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.904 -10.469   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.245  -8.762   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.775  -8.937   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.074  -7.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.043  -6.426   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.422  -8.709   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.243  -7.222   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.910  -7.218   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -2.905  -2.598   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.239  -4.142   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.237  -1.827   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.335  -9.552   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   18   42                                             
CONECT   14   13    5   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   22                                             
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   40                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   41                                                  
CONECT   28   27   29   39                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37   30   33                                                  
CONECT   39   37   28   40                                                  
CONECT   40   39   25                                                       
CONECT   41   27                                                            
CONECT   42   13                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Ergocryptine phosphate, (5'alpha)-isomer	MeSH
Ergocryptine mesylate	MeSH
Ergokryptin	MeSH
Ergocryptine monomethanesulfonate, (5'alpha,8alpha)-isomer	MeSH
Ergocryptine, (5'alpha(S),8alpha)-isomer	MeSH
Ergocryptine sulfate, (1:1) salt, (5'alpha)-isomer	MeSH
Ergocryptine citrate, (5'alpha)-isomer	MeSH
Ergocryptine monomethanesulfonate, (5'alpha)-isomer	MeSH
Ergocryptine tartrate, (5'alpha)-isomer	MeSH
Ergocryptine, (5'alpha,8alpha)-isomer	MeSH
alpha-Ergocryptine	MeSH

Chemical Formula

C₃₂H₄₁N₅O₅

Average Mass

575.6984 Da

Monoisotopic Mass

575.31077 Da

IUPAC Name

N-[2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

ergocryptine

CAS Registry Number

Not Available

SMILES

CC(C)CC1N2C(=O)C(NC(=O)C3CN(C)C4CC5=CNC6=CC=CC(=C56)C4=C3)(OC2(O)C2CCCN2C1=O)C(C)C

InChI Identifier

InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)

InChI Key

YDOTUXAWKBPQJW-UHFFFAOYSA-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

Species Name	Source	Reference
Claviceps purpurea	LOTUS Database	35616633
Claviceps zizaniae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergopeptines

Alternative Parents

Substituents

Hybrid peptide
Ergopeptine
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Benzenoid
Oxazolidinone
Piperazine
Pyrrolidine
Pyrrole
Heteroaromatic compound
Tertiary carboxylic acid amide
Oxazolidine
Carboxamide group
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Tertiary amine
Orthocarboxylic acid derivative
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Alkanolamine
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	3.29	ALOGPS
logP	3.31	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	158.11 m³·mol⁻¹	ChemAxon
Polarizability	61.18 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	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergocryptine

METLIN ID

Not Available

PubChem Compound

99049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0147454)

MOL for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D MOL for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D SDF for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D-SDF for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

PDB for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D PDB for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

SMILES for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

INCHI for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

Structure for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D Structure for NP0147454 (n-[2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)