NP-MRD: Showing NP-Card for methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0245230)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 06:14:21 UTC

Updated at

2022-09-07 06:14:21 UTC

NP-MRD ID

NP0245230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate

Description

Methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2(7),3,5,9-tetraene-10-carboxylate 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. Based on a literature review very few articles have been published on methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2(7),3,5,9-tetraene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208142D          

 43 48  0  0  1  0            999 V2000
    2.0785    5.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    4.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    4.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    3.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    3.1826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946    1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.2397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4885    1.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.1301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    2.4647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9183    2.9846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076    4.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    4.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    5.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    5.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268    6.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138    6.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839    7.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    8.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    9.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867    8.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166    8.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2240    9.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273    7.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6978    7.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    6.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.9448    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 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  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 30 41  1  0  0  0  0
 22 42  1  0  0  0  0
  5 42  1  0  0  0  0
 22 43  1  0  0  0  0
 43 18  1  1  0  0  0
 15 43  1  0  0  0  0
M  END

     RDKit          3D

 81 86  0  0  0  0  0  0  0  0999 V2000
   -5.2311   -5.5258    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -4.3720    0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6757   -3.1321   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737   -3.0644   -1.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069   -1.9470    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -0.7765   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357   -0.3645   -1.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4113    0.9620   -1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.8084   -2.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846    3.0420   -2.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3916    3.8708   -3.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1645    3.4832   -1.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8848    2.6480   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    1.3961   -0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4513    0.3772    0.3277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1857    1.0030    1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    1.2908    2.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    1.1992    1.7303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592    1.1901    2.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -0.1464    2.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0550   -1.2853    2.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061   -1.2406    1.3285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1079   -2.0281    0.2545 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9112   -3.4764    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1543   -1.4580   -0.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.9665   -1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132   -1.0138   -2.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483   -0.3889   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -0.3531   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.1936   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.7324   -1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8606    1.2320   -1.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962    1.7752   -2.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971    1.7991   -3.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6444    1.2123   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9272    1.7210   -0.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1584    3.0851   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229    0.6727    0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9343    0.6616    1.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4020    0.1084    2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    0.1810    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.9645    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0457    0.1350    0.7773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6166   -6.1779    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5964   -6.0790   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1228   -5.1683   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5332   -0.9442   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4228    1.4434   -3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1659    4.5154   -3.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705    4.4482   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643    2.9916   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533    0.3845    1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6748    1.9602    1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1118    0.6926    3.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641    2.3680    2.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    1.7737    3.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    1.8343    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8827   -0.2868    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441   -0.1772    3.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5051   -2.2351    2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932   -1.3083    3.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -1.9801   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507   -4.0652    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -3.8962   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813   -3.6923    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401    0.0018   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -0.7609    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    0.7553   -2.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    2.3587   -3.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    0.7323   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215    2.3299   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6054    3.5867   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7908    3.2173    0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1948    3.6026   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5686    0.7336    3.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9650   -0.8992    2.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1636   -0.0119    3.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4386   -0.2431    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -2.9912    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295   -1.4536    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    0.3640   -0.0836 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  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  1
 22 42  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 22 43  1  0
 42  5  1  0
 41 30  1  0
 15  6  1  0
 43 15  1  0
 14  8  1  0
 43 18  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  7 47  1  0
  9 48  1  0
 11 49  1  0
 12 50  1  0
 13 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 42 79  1  0
 42 80  1  0
 23 62  1  6
 24 63  1  0
 24 64  1  0
 24 65  1  0
 28 66  1  0
 29 67  1  0
 31 68  1  0
 34 69  1  0
 34 70  1  0
 34 71  1  0
 37 72  1  0
 37 73  1  0
 37 74  1  0
 40 75  1  0
 40 76  1  0
 40 77  1  0
 41 78  1  0
 43 81  1  6
M  END


  Mrv1652309072208142D          

 43 48  0  0  1  0            999 V2000
    2.0785    5.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    4.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    4.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    3.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    3.1826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946    1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.2397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4885    1.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.1301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    2.4647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9183    2.9846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076    4.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    4.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    5.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    5.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268    6.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138    6.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839    7.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    8.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    9.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867    8.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166    8.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2240    9.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273    7.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6978    7.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    6.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.9448    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 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  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 30 41  1  0  0  0  0
 22 42  1  0  0  0  0
  5 42  1  0  0  0  0
 22 43  1  0  0  0  0
 43 18  1  1  0  0  0
 15 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC(O)=CC=C3[C@@]22CCN3CCC[C@](C1)([C@H](C)OC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C33H38N2O8/c1-19(43-27(37)10-7-20-15-25(39-2)28(41-4)26(16-20)40-3)32-11-6-13-35-14-12-33(31(32)35)23-9-8-21(36)17-24(23)34-29(33)22(18-32)30(38)42-5/h7-10,15-17,19,31,34,36H,6,11-14,18H2,1-5H3/b10-7+/t19-,31-,32-,33-/m0/s1

> <INCHI_KEY>
MEYAQWDYSCOEHW-NIPXWFQUSA-N

> <FORMULA>
C33H38N2O8

> <MOLECULAR_WEIGHT>
590.673

> <EXACT_MASS>
590.262816192

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
63.512373398188345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_LOGP>
3.0311163895689894

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.55912850238196

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.44480482490995

> <JCHEM_PKA_STRONGEST_BASIC>
10.076651086168253

> <JCHEM_POLAR_SURFACE_AREA>
115.79

> <JCHEM_REFRACTIVITY>
162.81589999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.880  10.684   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.637   9.163   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.833   8.193   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.271   8.743   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.591   6.672   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.786   5.702   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.308   5.941   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.005   4.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.493   4.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.890   2.680   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.377   2.280   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.799   1.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.312   1.992   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.915   3.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.544   4.181   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.512   2.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.672   1.692   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.863   2.110   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.425   1.559   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.229   2.530   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.472   4.050   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.910   4.601   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.714   5.571   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.276   5.021   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.957   7.092   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.761   8.062   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.677   7.512   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.003   9.583   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.192  10.554   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.050  12.074   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.146  13.045   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.903  14.566   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.099  15.536   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.856  17.057   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.535  15.116   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.778  16.637   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.418  17.607   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.731  14.146   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.169  14.696   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.365  13.725   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.488  12.625   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.152   6.122   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.106   3.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   42                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    6   16   43                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   43                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   42   43                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   41                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   30                                                       
CONECT   42   22    5                                                       
CONECT   43   22   18   15                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₈N₂O₈

Average Mass

590.6730 Da

Monoisotopic Mass

590.26282 Da

IUPAC Name

methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=CC(O)=CC=C3[C@@]22CCN3CCC[C@](C1)([C@H](C)OC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1)[C@@H]23

InChI Identifier

InChI=1S/C33H38N2O8/c1-19(43-27(37)10-7-20-15-25(39-2)28(41-4)26(16-20)40-3)32-11-6-13-35-14-12-33(31(32)35)23-9-8-21(36)17-24(23)34-29(33)22(18-32)30(38)42-5/h7-10,15-17,19,31,34,36H,6,11-14,18H2,1-5H3/b10-7+/t19-,31-,32-,33-/m0/s1

InChI Key

MEYAQWDYSCOEHW-NIPXWFQUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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
Plumeran-type alkaloid
Carbazole
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Indolizidine
Dihydroindole
Indole or derivatives
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Anisole
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
N-alkylpyrrolidine
Monocyclic benzene moiety
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Enamine
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organonitrogen compound
Organopnictogen 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	3.03	ChemAxon
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	162.82 m³·mol⁻¹	ChemAxon
Polarizability	63.51 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163191220

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0245230)

MOL for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D MOL for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D SDF for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D-SDF for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

PDB for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D PDB for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

SMILES for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

INCHI for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

Structure for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D Structure for NP0245230 (methyl (1r,12r,19r)-5-hydroxy-12-[(1s)-1-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)