NP-MRD: Showing NP-Card for (1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione (NP0265377)

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Record Information

Version

2.0

Created at

2022-09-08 09:19:59 UTC

Updated at

2022-09-08 09:19:59 UTC

NP-MRD ID

NP0265377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione

Description

Novacine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Novacine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione is found in Strychnos icaja, Strychnos nux-vomica and Strychnos wallichiana. (1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione was first documented in 1993 (PMID: 7912074). Based on a literature review a small amount of articles have been published on novacine (PMID: 30079716).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211202D          

 31 36  0  0  1  0            999 V2000
    6.6571    0.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6794   -0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2510   -0.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5479   -0.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702   -1.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9986   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7240   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7462   -2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -1.5817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9586   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -3.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971   -3.3043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -4.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -0.0097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.1956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5784    0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009    0.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8676    1.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -0.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -1.0039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4675   -0.9399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7962   -1.4196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3565   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508   -3.2505    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  6  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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  1  0  0  0
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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 26 25  1  6  0  0  0
 11 26  1  0  0  0  0
 27 26  1  1  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
    5.7819   -2.4092    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263   -1.0186    0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -0.6306    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1534   -1.5190    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -1.1261    0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5336    0.2147   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6040    1.1160   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.7114    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618    1.6190    0.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    3.0123   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573    0.4271   -0.1607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2528    1.1654   -1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712    2.4572   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    2.3780   -0.4996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202    3.6829   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.3977   -0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492    0.1462   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.7496   -0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782   -2.2153   -0.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -2.7428   -0.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -2.5908    0.7273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9969   -3.6360    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151   -3.2116    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718   -4.1285    0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046   -1.8574    0.0762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987   -0.9689   -0.1973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4813   -1.2489    0.9365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4527   -0.1094    1.0975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7162    1.0420    1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4135    1.2224    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114    2.1200    1.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8633   -2.5736    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -2.9765   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -2.8374    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -2.5909    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3600    2.1753   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3520    3.2334   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    3.6290    0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589    3.3291    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886    0.4677   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    1.4098   -1.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848    3.1378   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1027    2.9209   -2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5246    4.3022    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    3.5892   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    4.2426   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8232    1.1272   -2.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1536    1.8386   -1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363   -0.3630   -1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4390   -2.3107    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6641   -2.7261   -1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -2.7626    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735   -4.5493    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9202   -4.0380    1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082   -1.1912   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -1.2827    1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192   -0.4385    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4226    0.7247    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2837    1.9634    1.8235 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
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 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
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 17 18  2  0
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 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
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 28 29  1  0
 29 30  1  0
 30 31  2  0
  8  3  1  0
 26 11  1  0
 25  5  1  0
 11 30  1  1
 28 17  1  0
 27 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
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 13 42  1  0
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 15 44  1  0
 15 45  1  0
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 16 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
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 21 52  1  1
 22 53  1  0
 22 54  1  0
 26 55  1  6
 27 56  1  1
 28 57  1  1
 29 58  1  0
 29 59  1  0
M  END


  Mrv1652309082211202D          

 31 36  0  0  1  0            999 V2000
    6.6571    0.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6794   -0.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -0.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2510   -0.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5479   -0.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702   -1.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9986   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7240   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7462   -2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -1.5817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9586   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -3.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971   -3.3043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -4.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -0.0097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.1956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5784    0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009    0.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8676    1.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -0.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -1.0039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4675   -0.9399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7962   -1.4196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3565   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508   -3.2505    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  6  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
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 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 26 25  1  6  0  0  0
 11 26  1  0  0  0  0
 27 26  1  1  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
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 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0265377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@]13CCN(C)CC4=CCO[C@H]5CC(=O)N2[C@H]1[C@H]5[C@H]4CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O5/c1-25-6-5-24-15-9-17(29-2)18(30-3)10-16(15)26-21(28)11-19-22(23(24)26)14(8-20(24)27)13(12-25)4-7-31-19/h4,9-10,14,19,22-23H,5-8,11-12H2,1-3H3/t14-,19-,22-,23-,24+/m0/s1

> <INCHI_KEY>
POLBLONFVZXVPI-SVFVWZOVSA-N

> <FORMULA>
C24H28N2O5

> <MOLECULAR_WEIGHT>
424.497

> <EXACT_MASS>
424.19982201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.13420601237763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S,11R,12S,22R)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

> <JCHEM_LOGP>
0.656129441333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.924745212917262

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.221080548967706

> <JCHEM_PKA_STRONGEST_BASIC>
8.282736757017046

> <JCHEM_POLAR_SURFACE_AREA>
68.31

> <JCHEM_REFRACTIVITY>
114.8731

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S,11R,12S,22R)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      12.427   1.377   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.468  -0.162   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.156  -0.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.802  -0.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.489  -1.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.531  -2.580   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.885  -3.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.197  -2.508   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.551  -3.241   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.593  -4.781   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.241  -2.953   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.389  -4.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.518  -5.755   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.035  -6.168   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.915  -7.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.633  -5.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.969  -4.141   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.230  -2.515   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.235  -0.975   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.441  -0.018   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.942  -0.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.813   0.905   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.348   0.785   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.220   2.055   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.012  -0.604   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.141  -1.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.606  -1.754   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.353  -2.650   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.399  -4.414   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.934  -4.533   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.068  -6.068   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   26   30                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25   11   27                                                  
CONECT   27   26   21   28                                                  
CONECT   28   27   17   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   11   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dimethoxy-19-methyl-16,19-seco-strychnidine-10,16-dione	ChEBI

Chemical Formula

C₂₄H₂₈N₂O₅

Average Mass

424.4970 Da

Monoisotopic Mass

424.19982 Da

IUPAC Name

(1S,10S,11R,12S,22R)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

Traditional Name

(1S,10S,11R,12S,22R)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@]13CCN(C)CC4=CCO[C@H]5CC(=O)N2[C@H]1[C@H]5[C@H]4CC3=O

InChI Identifier

InChI=1S/C24H28N2O5/c1-25-6-5-24-15-9-17(29-2)18(30-3)10-16(15)26-21(28)11-19-22(23(24)26)14(8-20(24)27)13(12-25)4-7-31-19/h4,9-10,14,19,22-23H,5-8,11-12H2,1-3H3/t14-,19-,22-,23-,24+/m0/s1

InChI Key

POLBLONFVZXVPI-SVFVWZOVSA-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
Strychnos icaja	LOTUS Database	35616633
Strychnos nux-vomica	LOTUS Database	35616633
Strychnos wallichiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Quinolidine
Anisole
Phenol ether
Alkyl aryl ether
Delta-lactam
Aralkylamine
Piperidinone
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Ketone
Lactam
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
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	0.66	ChemAxon
pKa (Strongest Acidic)	17.22	ChemAxon
pKa (Strongest Basic)	8.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.87 m³·mol⁻¹	ChemAxon
Polarizability	45.13 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28643229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314414

PDB ID

Not Available

ChEBI ID

132669

Good Scents ID

Not Available

References

General References

Yang XW, Yan ZK: [Studies on the chemical constituents of alkaloids in seeds of Strychnos nux-vomica L]. Zhongguo Zhong Yao Za Zhi. 1993 Dec;18(12):739-40, 763-4. [PubMed:7912074 ]
Xie BX, Tang WZ, Wang LH, Wang XJ: [Study on Chemical Constituents of Strychnos nux-vomica]. Zhong Yao Cai. 2016 Jan;39(1):86-9. [PubMed:30079716 ]
LOTUS database [Link]

Showing NP-Card for (1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione (NP0265377)

MOL for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

3D MOL for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

3D SDF for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

3D-SDF for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

PDB for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

3D PDB for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

SMILES for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

INCHI for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

Structure for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)

3D Structure for NP0265377 ((1s,10s,11r,12s,22r)-16,17-dimethoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14(19),15,17-tetraene-20,23-dione)