NP-MRD: Showing NP-Card for Usambarine (NP0050916)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:23:01 UTC

Updated at

2022-04-27 22:23:01 UTC

NP-MRD ID

NP0050916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Usambarine

Description

(2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11,13,15-tetraene 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. Usambarine is found in Strychnos usambarensis. Based on a literature review very few articles have been published on (2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11,13,15-tetraene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200232D          

 34 40  0  0  1  0            999 V2000
    2.7440    1.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -0.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031    0.6508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3580    1.4354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8060    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990    1.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170    0.9938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4621    0.2092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6551    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -0.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7592   -1.1885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3112   -1.8016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6972   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847   -0.8751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -1.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5240    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7789    1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    1.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 12 14  1  1  0  0  0
 15 14  1  6  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  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  2  0  0  0  0
 16 28  1  0  0  0  0
 11 29  1  1  0  0  0
 29 30  2  0  0  0  0
  3 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  2 34  2  0  0  0  0
M  END

     RDKit          3D

 68 74  0  0  0  0  0  0  0  0999 V2000
   -0.4956   -3.5163   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8872   -2.2956   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -1.3711    0.7588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9171   -0.9915    1.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -0.6686    1.3581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786   -0.6681    2.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5838   -0.6698    1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    0.4856    0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3755    1.0608    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298    2.0677   -0.6260 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0631    2.1376   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9256    2.9638   -1.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2914    2.7930   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8631    1.8041   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0170    0.9841    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6382    1.1534    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.5778    0.6676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1385    0.4360   -0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2246   -0.1205   -0.0609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0021   -0.3891   -1.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4065   -0.9076   -1.1221 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3280    0.1440   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    1.4984   -0.5856 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3977    2.0043   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8787    3.2737    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1398    3.4382    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9872    2.3836    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5150    1.1010    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2567    0.9602    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596   -0.1748   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -1.6321   -0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503   -2.2778    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -2.1457   -0.4758 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590   -3.2502   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -4.2242   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4494   -3.8700    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8498   -1.9517   -0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.8101    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -1.8751    2.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269   -0.0761    2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2224   -1.5971    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2907    0.2322    2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6666   -1.6253    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702   -0.6274    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0886    2.7378   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5003    3.7470   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9499    3.4505   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9400    1.7268   -0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4357    0.2061    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790    1.2908    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327    1.4432   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -0.1672   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.6532    0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -1.1323   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    0.5245   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280   -1.0829   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4293    2.0367   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2094    4.0984   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4778    4.4590    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9771    2.5407    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1468    0.2484    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -2.0342   -1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7264   -1.8077    0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190   -3.3399    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4854   -1.8160    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538   -3.0344   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383   -3.3743   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9783   -4.1378   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 21 33  1  0
  3 19  1  0
 29 30  1  0
  9 17  1  0
 16 11  1  0
 29 24  1  0
 16  8  1  0
 34 66  1  0
 34 67  1  0
 34 68  1  0
 32 64  1  0
 32 65  1  0
 31 62  1  0
 31 63  1  0
 23 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 21 56  1  6
 20 54  1  0
 20 55  1  0
 19 53  1  1
 18 51  1  0
 18 52  1  0
 17 50  1  1
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
 10 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
  4 39  1  0
  4 40  1  0
  3 38  1  1
  2 37  1  0
  1 35  1  0
  1 36  1  0
M  END


  Mrv1652304282200232D          

 34 40  0  0  1  0            999 V2000
    2.7440    1.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -0.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031    0.6508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3580    1.4354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8060    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990    1.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170    0.9938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4621    0.2092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6551    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -0.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7592   -1.1885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3112   -1.8016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6972   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847   -0.8751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -1.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5240    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7789    1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    1.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 12 14  1  1  0  0  0
 15 14  1  6  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  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  2  0  0  0  0
 16 28  1  0  0  0  0
 11 29  1  1  0  0  0
 29 30  2  0  0  0  0
  3 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  2 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=C(NC3=CC=CC=C23)[C@@H]1C[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC=C32)C[C@H]1C=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H34N4/c1-3-19-18-34-15-13-24-22-9-5-7-11-26(22)32-30(24)28(34)17-20(19)16-27-29-23(12-14-33(27)2)21-8-4-6-10-25(21)31-29/h3-11,19-20,27-28,31-32H,1,12-18H2,2H3/t19-,20+,27+,28+/m1/s1

> <INCHI_KEY>
JICXOAIUPFUZPK-MVOSJVTLSA-N

> <FORMULA>
C30H34N4

> <MOLECULAR_WEIGHT>
450.63

> <EXACT_MASS>
450.278347111

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.217748949014805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
5.235528402

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.67617948013882

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.07411939607355

> <JCHEM_PKA_STRONGEST_BASIC>
7.8267691941002955

> <JCHEM_POLAR_SURFACE_AREA>
38.06

> <JCHEM_REFRACTIVITY>
141.16469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.122   2.039   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.715   1.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.876  -0.119   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.383  -0.439   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.153   0.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.659   1.215   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.135   2.679   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.104   3.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.598   3.504   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.641   3.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.672   1.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.196   0.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.689   0.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.226  -0.754   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.750  -2.219   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.781  -3.363   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      11.305  -4.828   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.799  -5.148   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.768  -4.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.244  -2.539   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       7.998  -1.634   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       6.752  -2.539   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.228  -4.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.198  -5.148   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.691  -4.828   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.215  -3.363   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.246  -2.219   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.287  -3.043   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.178   2.175   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.654   3.640   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.630  -1.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.224  -0.398   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.063   1.134   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.309   2.039   0.000  0.00  0.00           C+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    6                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   19   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   16                                                            
CONECT   29   11   30                                                       
CONECT   30   29                                                            
CONECT   31    3   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄N₄

Average Mass

450.6300 Da

Monoisotopic Mass

450.27835 Da

IUPAC Name

(2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene

Traditional Name

(2S,4S,5S)-5-ethenyl-4-{[(1S)-2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene

CAS Registry Number

Not Available

SMILES

CN1CCC2=C(NC3=CC=CC=C23)[C@@H]1C[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC=C32)C[C@H]1C=C

InChI Identifier

InChI=1S/C30H34N4/c1-3-19-18-34-15-13-24-22-9-5-7-11-26(22)32-30(24)28(34)17-20(19)16-27-29-23(12-14-33(27)2)21-8-4-6-10-25(21)31-29/h3-11,19-20,27-28,31-32H,1,12-18H2,2H3/t19-,20+,27+,28+/m1/s1

InChI Key

JICXOAIUPFUZPK-MVOSJVTLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strychnos usambarensis	Plant	KNApSAcK

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
Pyridoindole
Beta-carboline
3-alkylindole
Quinolizine
Indole or derivatives
Indole
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
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	4.72	ALOGPS
logP	5.24	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.07	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	38.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	141.16 m³·mol⁻¹	ChemAxon
Polarizability	55.22 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

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

163049096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Usambarine (NP0050916)

MOL for NP0050916 (Usambarine)

3D MOL for NP0050916 (Usambarine)

3D SDF for NP0050916 (Usambarine)

3D-SDF for NP0050916 (Usambarine)

PDB for NP0050916 (Usambarine)

3D PDB for NP0050916 (Usambarine)

SMILES for NP0050916 (Usambarine)

INCHI for NP0050916 (Usambarine)

Structure for NP0050916 (Usambarine)

3D Structure for NP0050916 (Usambarine)