NP-MRD: Showing NP-Card for Vobtusine (NP0050923)

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Record Information

Version

1.0

Created at

2022-04-27 22:23:21 UTC

Updated at

2022-04-27 22:23:21 UTC

NP-MRD ID

NP0050923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vobtusine

Description

Vobtusine belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. Vobtusine is found in Tabernaemontana sphaerocarpa, Voacanga africana Stapf. , Voacanga obtusa, Voacanga spp. and Voacanga thouarsii. It was first documented in 2009 (PMID: 19921789). Based on a literature review a significant number of articles have been published on vobtusine (PMID: 22822667) (PMID: 35164343) (PMID: 33462757) (PMID: 21546135).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200232D          

 53 65  0  0  1  0            999 V2000
    2.5228    5.3200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7973    4.9273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0944    5.3593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1442    6.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427    6.5767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5455    6.1447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2711    6.5374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    7.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    7.4014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0880    7.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    7.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    6.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8033    5.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    5.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3689    4.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    4.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0491    3.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    4.1026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7644    4.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1205    4.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9431    4.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095    4.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    3.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308    3.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    2.5825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0521    2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    4.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494    4.4485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265    3.6427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6171    3.0865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1692    3.3361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6496    2.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601    2.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805    2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898    2.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128    3.3931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7244    3.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413    3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109    2.5067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1242    3.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902    4.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    4.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905    4.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    4.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5439    0.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482    0.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    4.4953    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
  3  4  1  6  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  6  0  0  0
  3 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 35  1  6  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 39 38  1  1  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 38 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 40 46  1  0  0  0  0
 39 47  1  0  0  0  0
 47 48  1  0  0  0  0
 29 48  1  0  0  0  0
 37 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
  2 53  1  6  0  0  0
M  END

     RDKit          3D

103115  0  0  0  0  0  0  0  0999 V2000
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    5.9483   -2.5286    2.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8051    1.9754   -0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823    0.5896   -0.6415 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.6899    0.7093    0.1971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4096    1.9555    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4650   -1.1935    0.9761 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0398   -1.2875    2.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7525   -2.1167    1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4770    1.3491   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 13 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 18  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 33 32  1  1
 33 46  1  0
 33 34  1  0
 34 41  2  0
 41 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  1
 41 38  1  0
 38 39  1  0
 39 40  1  0
 38 37  2  0
 37 36  1  0
 36 35  2  0
 19 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 51 50  1  1
 51 52  1  0
 51 53  1  0
 52  5  1  0
 14  6  1  0
 53 14  1  0
  9  8  1  0
 53 17  1  0
 43 19  1  0
 51 47  1  0
 44 21  1  0
 27 23  1  0
 46 30  1  0
 35 34  1  0
 46 23  1  0
 44 33  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  7 57  1  0
 12 61  1  0
 11 60  1  0
 10 59  1  0
  9 58  1  0
 15 62  1  0
 15 63  1  0
 16 64  1  0
 16 65  1  0
 18 66  1  0
 18 67  1  0
 20 68  1  0
 20 69  1  0
 21 70  1  6
 22 71  1  0
 22 72  1  0
 24 73  1  0
 24 74  1  0
 25 75  1  0
 25 76  1  0
 27 77  1  6
 28 78  1  0
 28 79  1  0
 29 80  1  0
 29 81  1  0
 31 82  1  0
 31 83  1  0
 32 84  1  0
 32 85  1  0
 46 95  1  6
 43 92  1  0
 43 93  1  0
 45 94  1  0
 40 89  1  0
 40 90  1  0
 40 91  1  0
 37 88  1  0
 36 87  1  0
 35 86  1  0
 47 96  1  6
 49 97  1  0
 49 98  1  0
 50 99  1  0
 50100  1  0
 52101  1  0
 52102  1  0
 53103  1  1
M  END


  Mrv1652304282200232D          

 53 65  0  0  1  0            999 V2000
    2.5228    5.3200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7973    4.9273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0944    5.3593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1442    6.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427    6.5767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5455    6.1447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2711    6.5374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    7.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    7.4014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0880    7.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    7.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    6.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8033    5.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    5.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3689    4.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    4.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0491    3.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    4.1026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7644    4.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1205    4.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9431    4.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095    4.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    3.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308    3.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    2.5825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0521    2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    4.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494    4.4485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2265    3.6427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6171    3.0865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1692    3.3361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6496    2.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601    2.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805    2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898    2.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128    3.3931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7244    3.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413    3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109    2.5067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1242    3.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902    4.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    4.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905    4.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    4.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5439    0.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482    0.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253   -0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    4.4953    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
  3  4  1  6  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  6  0  0  0
  3 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 35  1  6  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 39 38  1  1  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 38 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 40 46  1  0  0  0  0
 39 47  1  0  0  0  0
 47 48  1  0  0  0  0
 29 48  1  0  0  0  0
 37 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
  2 53  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=C(C=CC=C3)[C@@]22CCN3C[C@]4(C[C@@H]5C[C@]67CCO[C@H]6CCN6CC[C@]8([C@H]76)C6=C(N(C4)[C@@]58O)C(OC)=CC=C6)[C@@H]4OCC[C@]4(C1)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C43H50N4O6/c1-50-30-9-5-7-28-32(30)47-24-38(20-25-21-39-13-18-52-31(39)10-15-45-17-12-42(28,36(39)45)43(25,47)49)23-46-16-11-41-27-6-3-4-8-29(27)44-33(41)26(34(48)51-2)22-40(35(41)46)14-19-53-37(38)40/h3-9,25,31,35-37,44,49H,10-24H2,1-2H3/t25-,31+,35+,36+,37+,38+,39-,40+,41+,42-,43-/m1/s1

> <INCHI_KEY>
IIMPGJMHQMBXKL-OPDPKHDKSA-N

> <FORMULA>
C43H50N4O6

> <MOLECULAR_WEIGHT>
718.895

> <EXACT_MASS>
718.373035346

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
79.78870397275814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,1'R,7S,11R,12'R,13R,15S,16'S,22'R,24R,25S)-24-hydroxy-19-methoxy-8,15'-dioxa-4,8',17,19'-tetraazaspiro[heptacyclo[11.10.1.1^{1,4}.0^{7,11}.0^{17,24}.0^{18,23}.0^{11,25}]pentacosane-15,17'-hexacyclo[10.9.1.0^{1,9}.0^{2,7}.0^{12,16}.0^{19,22}]docosane]-2'(7'),3',5',9',18(23),19,21-heptaene-10'-carboxylate

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
2.7881974576666653

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.081911259131836

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.406969938611272

> <JCHEM_PKA_STRONGEST_BASIC>
10.152750702540194

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
200.65129999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,1'R,7S,11R,12'R,13R,15S,16'S,22'R,24R,25S)-24-hydroxy-19-methoxy-8,15'-dioxa-4,8',17,19'-tetraazaspiro[heptacyclo[11.10.1.1^{1,4}.0^{7,11}.0^{17,24}.0^{18,23}.0^{11,25}]pentacosane-15,17'-hexacyclo[10.9.1.0^{1,9}.0^{2,7}.0^{12,16}.0^{19,22}]docosane]-2'(7'),3',5',9',18(23),19,21-heptaene-10'-carboxylate

> <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       4.709   9.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.355   9.198   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.043  10.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.136  11.332   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.440  12.276   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.752  11.470   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.106  12.203   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.148  13.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.836  14.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.482  13.816   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.031  14.332   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.092  13.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.962  11.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.099  10.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.160   9.415   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.689   9.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.646   7.732   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.958   6.925   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.313   7.658   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.160   7.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.825   8.869   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.360   8.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.231   7.718   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.566   6.329   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.031   6.210   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.366   4.821   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.831   4.702   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.491   8.770   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -1.959   8.304   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -2.289   6.800   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.152   5.762   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.316   6.227   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.213   4.975   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.299   3.736   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.951   4.272   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.482   4.257   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.950   3.791   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.088   4.830   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.757   6.334   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.086   7.113   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.237   6.090   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      -5.620   4.679   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      -7.698   6.576   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.008   8.085   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.857   9.107   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -5.396   8.621   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.654   7.586   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.740   8.826   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.281   2.287   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -4.749   1.821   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -2.143   1.249   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -2.474  -0.255   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       4.667   8.391   0.000  0.00  0.00           O+0
CONECT    1    2    6   15   21                                             
CONECT    2    1    3   19   53                                             
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   13                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5                                                       
CONECT   14    7   15                                                       
CONECT   15   14    1                                                       
CONECT   16    3   17                                                       
CONECT   17   16   18   28   32                                             
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20    1   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   17   29                                                       
CONECT   29   28   30   48                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   32   35   36                                             
CONECT   32   31   17   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
CONECT   36   31   37                                                       
CONECT   37   36   38   49                                                  
CONECT   38   37   39   42                                                  
CONECT   39   38   30   40   47                                             
CONECT   40   39   41   46                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41   38                                                       
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   40                                                       
CONECT   47   39   48                                                       
CONECT   48   47   29                                                       
CONECT   49   37   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51                                                            
CONECT   53    2                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  130    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₅₀N₄O₆

Average Mass

718.8950 Da

Monoisotopic Mass

718.37304 Da

IUPAC Name

methyl (1R,1'R,7S,11R,12'R,13R,15S,16'S,22'R,24R,25S)-24-hydroxy-19-methoxy-8,15'-dioxa-4,8',17,19'-tetraazaspiro[heptacyclo[11.10.1.1^{1,4}.0^{7,11}.0^{17,24}.0^{18,23}.0^{11,25}]pentacosane-15,17'-hexacyclo[10.9.1.0^{1,9}.0^{2,7}.0^{12,16}.0^{19,22}]docosane]-2'(7'),3',5',9',18(23),19,21-heptaene-10'-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=C(C=CC=C3)[C@@]22CCN3C[C@]4(C[C@@H]5C[C@]67CCO[C@H]6CCN6CC[C@]8([C@H]76)C6=C(N(C4)[C@@]58O)C(OC)=CC=C6)[C@@H]4OCC[C@]4(C1)[C@@H]23

InChI Identifier

InChI=1S/C43H50N4O6/c1-50-30-9-5-7-28-32(30)47-24-38(20-25-21-39-13-18-52-31(39)10-15-45-17-12-42(28,36(39)45)43(25,47)49)23-46-16-11-41-27-6-3-4-8-29(27)44-33(41)26(34(48)51-2)22-40(35(41)46)14-19-53-37(38)40/h3-9,25,31,35-37,44,49H,10-24H2,1-2H3/t25-,31+,35+,36+,37+,38+,39-,40+,41+,42-,43-/m1/s1

InChI Key

IIMPGJMHQMBXKL-OPDPKHDKSA-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
Tabernaemontana sphaerocarpa	LOTUS Database	35616633
Voacanga africana Stapf.	Plant	KNApSAcK
Voacanga obtusa	Plant	KNApSAcK
Voacanga spp.	Plant	KNApSAcK
Voacanga thouarsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Carbazole
Azaspirodecane
Quinolidine
Indole or derivatives
Dihydroindole
Indolizidine
Anisole
Dialkylarylamine
Alkyl aryl ether
Aralkylamine
Secondary aliphatic/aromatic amine
Piperidine
Benzenoid
N-alkylpyrrolidine
Cyclic alcohol
Vinylogous amide
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Methyl ester
Enoate ester
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Alkanolamine
Dialkyl ether
Enamine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

spiro compound (CHEBI:10016 )
methyl ester (CHEBI:10016 )
hemiaminal (CHEBI:10016 )
indole alkaloid fundamental parent (CHEBI:10016 )
alkaloid ester (CHEBI:10016 )
vinca alkaloid (CHEBI:10016 )

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	3.6	ALOGPS
logP	2.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	200.65 m³·mol⁻¹	ChemAxon
Polarizability	79.79 Å³	ChemAxon
Number of Rings	13	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

C00001787

Chemspider ID

66217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vobtusine

METLIN ID

Not Available

PubChem Compound

73534

PDB ID

Not Available

ChEBI ID

10016

Good Scents ID

Not Available

References

General References

Mei L, Deng Y, Li F, Guo DL, Lu CY: [Study on the alkaloids constituents from Voacanga africana]. Zhong Yao Cai. 2012 Feb;35(2):226-9. [PubMed:22822667 ]
de Jesus MSM, Macabeo APG, Ramos JDA, de Leon VNO, Asamitsu K, Okamoto T: Voacanga globosa Spirobisindole Alkaloids Exert Antiviral Activity in HIV Latently Infected Cell Lines by Targeting the NF-kB Cascade: In Vitro and In Silico Investigations. Molecules. 2022 Feb 5;27(3):1078. doi: 10.3390/molecules27031078. [PubMed:35164343 ]
Nugroho AE, Ono Y, Jin E, Hirasawa Y, Kaneda T, Rahman A, Kusumawati I, Tougan T, Horii T, Zaini NC, Morita H: Bisindole alkaloids from Voacanga grandifolia leaves. J Nat Med. 2021 Mar;75(2):408-414. doi: 10.1007/s11418-020-01475-w. Epub 2021 Jan 19. [PubMed:33462757 ]
Macabeo AP, Vidar WS, Chen X, Decker M, Heilmann J, Wan B, Franzblau SG, Galvez EV, Aguinaldo MA, Cordell GA: Mycobacterium tuberculosis and cholinesterase inhibitors from Voacanga globosa. Eur J Med Chem. 2011 Jul;46(7):3118-23. doi: 10.1016/j.ejmech.2011.04.025. Epub 2011 Apr 19. [PubMed:21546135 ]
Hirasawa Y, Miyama S, Hosoya T, Koyama K, Rahman A, Kusumawati I, Zaini NC, Morita H: Alasmontamine A, A first tetrakis monoterpene indole alkaloid from Tabernaemontana elegans. Org Lett. 2009 Dec 17;11(24):5718-21. doi: 10.1021/ol902420s. [PubMed:19921789 ]

Showing NP-Card for Vobtusine (NP0050923)

MOL for NP0050923 (Vobtusine)

3D MOL for NP0050923 (Vobtusine)

3D SDF for NP0050923 (Vobtusine)

3D-SDF for NP0050923 (Vobtusine)

PDB for NP0050923 (Vobtusine)

3D PDB for NP0050923 (Vobtusine)

SMILES for NP0050923 (Vobtusine)

INCHI for NP0050923 (Vobtusine)

Structure for NP0050923 (Vobtusine)

3D Structure for NP0050923 (Vobtusine)