NP-MRD: Showing NP-Card for methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-2-enoyl)oxy]ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0195943)

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Record Information

Version

2.0

Created at

2022-09-04 13:54:44 UTC

Updated at

2022-09-04 13:54:44 UTC

NP-MRD ID

NP0195943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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

Echitovenidine 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. methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-2-enoyl)oxy]ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate is found in Alstonia venenata. Based on a literature review very few articles have been published on Echitovenidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215542D          

 32 36  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
    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  1  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4929    3.2096    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
   -1.2634    2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    3.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    4.2493    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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
 14 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  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 21 31  1  0  0  0  0
  5 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 17  1  1  0  0  0
 14 32  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
   -0.5458    4.3714   -3.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    2.9953   -3.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450    2.6546   -1.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377    3.5951   -0.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045    1.2873   -1.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498    0.9604   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104    1.7140    1.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677    0.8341    2.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307    1.1232    3.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745    0.0795    4.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4593   -1.2084    4.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001   -1.4776    2.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4563   -0.4423    1.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035   -0.4407    0.2897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9234   -0.8608   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449   -2.2180   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855   -2.5903   -0.3808 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8801   -3.7145   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657   -3.4283   -2.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -2.0630   -2.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495   -0.9569   -1.7728 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2779   -0.4599   -1.6868 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8361    0.0857   -2.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498    0.5628   -0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645    0.4317    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -0.6331    0.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941    1.4110    1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0947    1.2350    2.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340    0.0219    2.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1671    2.3065    3.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.2028   -2.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.3910   -0.4121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5446    4.8760   -3.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    4.4421   -4.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390    4.8372   -2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5829    2.7695    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218    2.1431    3.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    0.2772    5.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158   -2.0130    4.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088   -2.4855    2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825   -0.9474    0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4318   -0.1280   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9978   -2.2923   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3973   -2.9662   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -4.2895   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4411   -4.4145   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -4.1647   -3.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -3.5163   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967   -2.0572   -3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6598   -1.9038   -3.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.2712   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9131    1.2111   -2.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8945   -0.2180   -3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -0.0688   -3.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142    2.3048    1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6612   -0.0196    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.1529    3.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.8927    2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1297    2.2727    4.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593    3.3124    3.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    2.1184    4.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686   -0.1316   -2.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999    0.6251   -3.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -1.5494    0.2207 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  6
 21 31  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  3
 28 29  1  0
 28 30  1  0
 21 32  1  0
 31  5  1  0
 14  6  1  0
 32 14  1  0
 13  8  1  0
 32 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
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 20 49  1  0
 20 50  1  0
 31 62  1  0
 31 63  1  0
 22 51  1  1
 23 52  1  0
 23 53  1  0
 23 54  1  0
 27 55  1  0
 29 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 32 64  1  1
M  END


  Mrv1652309042215542D          

 32 36  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
    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  1  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4929    3.2096    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
   -1.2634    2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    3.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    4.2493    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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
 14 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
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 21 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 21 31  1  0  0  0  0
  5 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 17  1  1  0  0  0
 14 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195943

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N2O4/c1-16(2)14-21(29)32-17(3)25-10-7-12-28-13-11-26(24(25)28)19-8-5-6-9-20(19)27-22(26)18(15-25)23(30)31-4/h5-6,8-9,14,17,24,27H,7,10-13,15H2,1-4H3/t17-,24+,25+,26+/m1/s1

> <INCHI_KEY>
JJCJKGZUGDPHMN-XRNKBYASSA-N

> <FORMULA>
C26H32N2O4

> <MOLECULAR_WEIGHT>
436.552

> <EXACT_MASS>
436.236207518

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.93236404509535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12R,19R)-12-[(1R)-1-[(3-methylbut-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>
3.545814892666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.072512659088634

> <JCHEM_PKA_STRONGEST_BASIC>
9.980516044031798

> <JCHEM_POLAR_SURFACE_AREA>
67.87

> <JCHEM_REFRACTIVITY>
125.63239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12R,19R)-12-[(1R)-1-[(3-methylbut-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                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  C   UNK     0       8.799   1.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.312   1.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.915   3.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.544   4.181   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.512   2.983   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.672   1.692   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.863   2.110   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.425   1.559   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.229   2.530   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.472   4.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.910   4.601   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.714   5.571   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.957   7.092   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.276   5.021   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.920   5.991   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.677   7.512   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.358   5.441   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.554   6.411   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.992   5.861   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.312   7.932   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.152   6.122   0.000  0.00  0.00           C+0
HETATM   32  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   31                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15   32                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31   32                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   21    5                                                       
CONECT   32   21   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂N₂O₄

Average Mass

436.5520 Da

Monoisotopic Mass

436.23621 Da

IUPAC Name

methyl (1R,12R,19R)-12-[(1R)-1-[(3-methylbut-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)-12-[(1R)-1-[(3-methylbut-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=CC=C3[C@@]22CCN3CCC[C@](C1)([C@@H](C)OC(=O)C=C(C)C)[C@@H]23

InChI Identifier

InChI=1S/C26H32N2O4/c1-16(2)14-21(29)32-17(3)25-10-7-12-28-13-11-26(24(25)28)19-8-5-6-9-20(19)27-22(26)18(15-25)23(30)31-4/h5-6,8-9,14,17,24,27H,7,10-13,15H2,1-4H3/t17-,24+,25+,26+/m1/s1

InChI Key

JJCJKGZUGDPHMN-XRNKBYASSA-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
Alstonia venenata	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
Plumeran-type alkaloid
Carbazole
Indole or derivatives
Dihydroindole
Indolizidine
Fatty acid ester
Aralkylamine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Fatty acyl
Piperidine
Benzenoid
N-alkylpyrrolidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Pyrrolidine
Enoate ester
Methyl ester
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Enamine
Azacycle
Organoheterocyclic compound
Amine
Organopnictogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen 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	3.55	ChemAxon
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	9.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.87 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.63 m³·mol⁻¹	ChemAxon
Polarizability	46.93 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

108341242

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134714947

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)-12-[(1r)-1-[(3-methylbut-2-enoyl)oxy]ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0195943)

MOL for NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-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 NP0195943 (methyl (1r,12r,19r)-12-[(1r)-1-[(3-methylbut-2-enoyl)oxy]ethyl]-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)