NP-MRD: Showing NP-Card for (2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol (NP0146270)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:38:07 UTC

Updated at

2022-09-02 01:38:07 UTC

NP-MRD ID

NP0146270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol

Description

(2S,4S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-15-[(2S)-1-methylpyrrolidin-2-yl]-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11(16),12,14-tetraen-14-ol belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. (2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol is found in Strychnos usambarensis. Based on a literature review very few articles have been published on (2S,4S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-15-[(2S)-1-methylpyrrolidin-2-yl]-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11(16),12,14-tetraen-14-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203382D          

 41 48  0  0  1  0            999 V2000
    0.1515   -1.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -1.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145   -1.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665   -2.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -3.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636   -3.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774   -4.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311   -4.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7860   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340   -6.1881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4135   -6.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -6.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910   -7.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -6.9950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -7.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -5.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8479   -6.5311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450   -5.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8901   -4.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -4.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -3.0212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5046   -3.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526   -2.5796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1456   -2.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -3.5358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9163   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -3.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -3.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102   -4.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552   -4.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -5.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -4.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712   -4.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -5.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1878   -4.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427   -4.1489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
 11 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 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
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 23  1  0  0  0  0
 11 23  1  0  0  0  0
 24  9  1  1  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 84 91  0  0  0  0  0  0  0  0999 V2000
   -0.1026   -0.0762   -3.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.7749   -2.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793   -1.9473   -1.7267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7229   -2.4576   -1.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -2.9387   -0.2056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -3.8211   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9274   -3.4085    1.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260   -2.0141    0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414   -1.1556    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.0460    0.3010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920    0.0243    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    1.0098    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7187    2.3876   -0.1744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8661    3.0972   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1709    4.1455   -1.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9051    3.3839   -2.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5298    2.6973   -0.8778 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7070    3.6543   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526    0.6250    0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4418    1.4798    0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7259   -0.6879    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7915   -1.6520    0.7999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571   -1.2595    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -1.8140    0.7089 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2446   -0.8956    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340   -1.7579   -0.3032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6399   -1.3805   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.1856    0.9362 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8133   -0.9185    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9439   -1.6712    0.7146 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279   -0.8931    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3674   -1.1481    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2712   -0.1373    0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8424    1.1667   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4833    1.4293    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5974    0.4044    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2304    0.3644    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136    1.4367    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.1805    1.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721   -0.1514    1.6965 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7388   -0.4389    3.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -0.2391   -3.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.7900   -3.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764   -0.4175   -2.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2755   -2.7871   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -1.6427   -1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9144   -3.3198   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -3.8744   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695   -4.8244    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611   -3.4741    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -4.0820    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    0.8680    0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    2.9110    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4674    2.4474   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5352    3.6472   -0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    4.3762   -2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196    5.0643   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675    2.6630   -2.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0901    4.0969   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9151    4.6958   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    3.6124    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366    3.4344   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3946    1.2072    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7654   -0.9795    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0298   -2.6816    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020   -2.2331    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -0.1016   -0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117   -0.4360    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676   -2.8005    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -2.2167   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023   -0.5018   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855   -2.1683    1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666   -2.7010    0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6982   -2.1887    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3405   -0.3372    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5739    1.9170   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1372    2.4395   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215    1.5855   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    2.4404    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    1.5853    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2537    1.7693    1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350   -1.5199    3.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.1999    3.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9812    0.2289    3.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 26  1  0
 26 27  1  0
 27 28  1  0
 28 40  1  0
 40 41  1  0
 40 39  1  0
 39 38  1  0
 38 37  1  0
 37 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 26 25  1  0
 25 24  1  0
  8 23  1  0
 23 22  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 13 17  1  0
 19 12  1  0
 23 11  1  0
 24  9  1  0
 24  5  1  0
 29 28  1  0
 36 31  1  0
 36 37  1  0
 18 60  1  0
 18 61  1  0
 18 62  1  0
 16 58  1  0
 16 59  1  0
 15 56  1  0
 15 57  1  0
 14 54  1  0
 14 55  1  0
 13 53  1  1
 10 52  1  0
  7 50  1  0
  7 51  1  0
  6 48  1  0
  6 49  1  0
  4 46  1  0
  4 47  1  0
  3 45  1  6
  2 44  1  0
  1 42  1  0
  1 43  1  0
 26 69  1  1
 27 70  1  0
 27 71  1  0
 28 72  1  1
 41 82  1  0
 41 83  1  0
 41 84  1  0
 39 80  1  0
 39 81  1  0
 38 78  1  0
 38 79  1  0
 30 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  0
 35 77  1  0
 25 67  1  0
 25 68  1  0
 24 66  1  1
 22 65  1  0
 21 64  1  0
 20 63  1  0
M  END


  Mrv1652309022203382D          

 41 48  0  0  1  0            999 V2000
    0.1515   -1.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -1.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145   -1.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665   -2.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9256   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -3.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636   -3.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774   -4.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311   -4.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7860   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340   -6.1881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4135   -6.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -6.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910   -7.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055   -6.9950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -7.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -5.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8479   -6.5311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450   -5.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8901   -4.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -4.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -3.0212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5046   -3.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526   -2.5796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1456   -2.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -3.5358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9163   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -3.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581   -3.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102   -4.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552   -4.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -5.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -4.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712   -4.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -5.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1878   -4.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427   -4.1489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
 11 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 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
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 23  1  0  0  0  0
 11 23  1  0  0  0  0
 24  9  1  1  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@H]1C1=C2NC3=C(CCN4CC(C=C)[C@@H](C[C@@H]5N(C)CCC6=C5NC5=CC=CC=C65)C[C@@H]34)C2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H43N5O/c1-4-21-20-40-17-14-26-24-11-12-31(41)32(28-10-7-15-38(28)2)35(24)37-34(26)30(40)19-22(21)18-29-33-25(13-16-39(29)3)23-8-5-6-9-27(23)36-33/h4-6,8-9,11-12,21-22,28-30,36-37,41H,1,7,10,13-20H2,2-3H3/t21?,22-,28-,29-,30-/m0/s1

> <INCHI_KEY>
PHLJPJICTIGOKC-QLDZTMMGSA-N

> <FORMULA>
C35H43N5O

> <MOLECULAR_WEIGHT>
549.763

> <EXACT_MASS>
549.346761025

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
65.41074189888471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,12bS)-3-ethenyl-2-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2S)-1-methylpyrrolidin-2-yl]-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-10-ol

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
3.970156852542162

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.276903838335407

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.05424461413343

> <JCHEM_PKA_STRONGEST_BASIC>
10.273419238516498

> <JCHEM_POLAR_SURFACE_AREA>
61.53

> <JCHEM_REFRACTIVITY>
168.89949999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,12bS)-3-ethenyl-2-{[(1S)-2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2S)-1-methylpyrrolidin-2-yl]-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-10-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.283  -2.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.224  -2.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.254  -3.351   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.760  -3.031   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -4.791  -4.175   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -6.297  -3.855   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.328  -4.999   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.852  -6.464   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.345  -6.784   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -5.184  -8.316   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -6.591  -8.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.067 -10.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.037 -11.551   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.505 -11.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.879 -12.797   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.023 -13.827   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -6.357 -13.057   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -7.764 -13.684   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.574 -10.727   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -9.049 -12.191   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.604  -9.582   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.128  -8.118   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.622  -7.798   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.315  -5.640   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.809  -5.960   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.778  -4.815   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.272  -5.136   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.204  -6.600   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.710  -6.920   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       2.956  -6.015   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       4.202  -6.920   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.709  -6.600   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.739  -7.745   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.263  -9.209   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.757  -9.529   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.726  -8.385   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.186  -8.385   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.156  -9.529   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.351  -9.209   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -0.826  -7.745   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      -2.333  -7.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   12   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    8   11                                                  
CONECT   24    9    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   40                                                  
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36   29   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   28   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₄₃N₅O

Average Mass

549.7630 Da

Monoisotopic Mass

549.34676 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CN1CCC[C@H]1C1=C2NC3=C(CCN4CC(C=C)[C@@H](C[C@@H]5N(C)CCC6=C5NC5=CC=CC=C65)C[C@@H]34)C2=CC=C1O

InChI Identifier

InChI=1S/C35H43N5O/c1-4-21-20-40-17-14-26-24-11-12-31(41)32(28-10-7-15-38(28)2)35(24)37-34(26)30(40)19-22(21)18-29-33-25(13-16-39(29)3)23-8-5-6-9-27(23)36-33/h4-6,8-9,11-12,21-22,28-30,36-37,41H,1,7,10,13-20H2,2-3H3/t21?,22-,28-,29-,30-/m0/s1

InChI Key

PHLJPJICTIGOKC-QLDZTMMGSA-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 usambarensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
2-phenylpyrrolidine
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
N-alkylpyrrolidine
Piperidine
Heteroaromatic compound
Pyrrole
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

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

101624708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol (NP0146270)

MOL for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

3D MOL for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

3D SDF for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

3D-SDF for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

PDB for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

3D PDB for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

SMILES for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

INCHI for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

Structure for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)

3D Structure for NP0146270 ((2s,12bs)-3-ethenyl-2-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-11-[(2s)-1-methylpyrrolidin-2-yl]-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-10-ol)