NP-MRD: Showing NP-Card for kopsine (NP0031116)

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Record Information

Version

2.0

Created at

2021-06-19 22:17:19 UTC

Updated at

2021-06-29 23:59:30 UTC

NP-MRD ID

NP0031116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kopsine

Provided By

JEOL Database JEOL Logo

Description

Kopsine belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. kopsine is found in Kopsia dasyrachis and Kopsia fruticosa. kopsine was first documented in 2005 (PMID: 15818570). Based on a literature review a small amount of articles have been published on Kopsine (PMID: 28230294) (PMID: 26717050).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100173D          

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     RDKit          3D

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   -1.4774   -0.0913    3.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    1.8923    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    2.9669    3.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    3.6465    1.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    1.6517   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    3.7112   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420    2.8591   -1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  1  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 21  5  1  6  0  0  0
 18 24  1  0  0  0  0
 11 10  2  0  0  0  0
 21 22  1  0  0  0  0
 24 22  1  0  0  0  0
 13 14  1  0  0  0  0
 10  9  1  0  0  0  0
 12 21  1  0  0  0  0
 12 11  1  6  0  0  0
 11  6  1  0  0  0  0
 14 28  1  0  0  0  0
 28 27  1  0  0  0  0
 27 12  1  0  0  0  0
 12 13  1  0  0  0  0
 22 25  1  0  0  0  0
 21 20  1  0  0  0  0
 13 36  1  1  0  0  0
 20 19  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 13 18  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  2  0  0  0  0
  3  4  2  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  1  0  0  0
  8  7  1  0  0  0  0
 25 26  2  0  0  0  0
  7  6  2  0  0  0  0
 27 25  1  0  0  0  0
 18 19  1  0  0  0  0
  9 34  1  0  0  0  0
  8 33  1  0  0  0  0
  7 32  1  0  0  0  0
 10 35  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 28 51  1  0  0  0  0
 28 52  1  0  0  0  0
 27 50  1  6  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 23 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)[C@@]3([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]5(C([H])([H])C([H])([H])[C@@]11N(C(=O)OC([H])([H])[H])C6=C([H])C([H])=C([H])C([H])=C6[C@@]31[C@@]45[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O4/c1-28-18(26)24-15-6-3-2-5-13(15)22-14-11-23-10-4-7-19(17(22)23)8-9-21(22,24)20(27,12-19)16(14)25/h2-3,5-6,14,17,27H,4,7-12H2,1H3/t14-,17+,19-,20-,21-,22+/m1/s1

> <INCHI_KEY>
YROYAGSZNDUMIF-MQVQQYNVSA-N

> <FORMULA>
C22H24N2O4

> <MOLECULAR_WEIGHT>
380.444

> <EXACT_MASS>
380.173607261

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.686128602559535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,3R,11S,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
1.5731823516666663

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.610015663242574

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.241485674148677

> <JCHEM_PKA_STRONGEST_BASIC>
8.76979511415103

> <JCHEM_POLAR_SURFACE_AREA>
70.08000000000001

> <JCHEM_REFRACTIVITY>
100.06939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3R,11S,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 58  0  0  0  0  0  0  0  0999 V2000
   -5.4338   -1.1617    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -1.1337   -0.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137   -0.2944    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223    0.3907    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -0.2368    0.2254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322   -1.0421   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217   -2.1545   -1.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -2.8015   -2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -2.3340   -2.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369   -1.2077   -1.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.5781   -0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.6948    0.0059 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5130    1.0300    0.7518 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2359    1.8887   -0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3654    2.5961    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    3.2758    1.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906    2.3209    2.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1425    1.6756    2.1220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5976    0.5277    2.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.1130    2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833    0.5973    0.9830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2426    2.1112    1.2353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3960    2.4442    1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    2.6982    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033    2.6476   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424    3.5746   -0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149    1.9114   -0.9235 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2810    2.7160   -0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773   -0.1740   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9041   -1.8678   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113   -1.5073    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -2.5604   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9626   -3.6804   -2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -2.8476   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -0.8249   -1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    0.1296    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    3.3281   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    1.8649    0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042    3.6393    2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4408    4.1602    1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1100    1.5415    3.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    2.8606    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -0.2354    3.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146    0.8964    3.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4059   -1.1757    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774   -0.0913    3.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    1.8923    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    2.9669    3.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    3.6465    1.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    1.6517   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    3.7112   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420    2.8591   -1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  1
 17 16  1  0
 16 15  1  0
 15 14  1  0
 21  5  1  6
 18 24  1  0
 11 10  2  0
 21 22  1  0
 24 22  1  0
 13 14  1  0
 10  9  1  0
 12 21  1  0
 12 11  1  6
 11  6  1  0
 14 28  1  0
 28 27  1  0
 27 12  1  0
 12 13  1  0
 22 25  1  0
 21 20  1  0
 13 36  1  1
 20 19  1  0
  5  3  1  0
  3  2  1  0
 13 18  1  0
  2  1  1  0
  9  8  2  0
  3  4  2  0
  6  5  1  0
 22 23  1  1
  8  7  1  0
 25 26  2  0
  7  6  2  0
 27 25  1  0
 18 19  1  0
  9 34  1  0
  8 33  1  0
  7 32  1  0
 10 35  1  0
 20 45  1  0
 20 46  1  0
 19 43  1  0
 19 44  1  0
 17 41  1  0
 17 42  1  0
 16 39  1  0
 16 40  1  0
 15 37  1  0
 15 38  1  0
 24 48  1  0
 24 49  1  0
 28 51  1  0
 28 52  1  0
 27 50  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 47  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.434  -1.162   0.020  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.034  -1.134  -0.264  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.314  -0.294   0.525  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.822   0.391   1.407  0.00  0.00           O+0
HETATM    5  N   UNK     0      -1.968  -0.237   0.225  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.232  -1.042  -0.685  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.622  -2.155  -1.411  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.672  -2.801  -2.212  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.647  -2.334  -2.286  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.037  -1.208  -1.565  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.090  -0.578  -0.770  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.230   0.695   0.006  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.513   1.030   0.752  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.236   1.889  -0.183  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.365   2.596   0.412  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.067   3.276   1.751  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.391   2.321   2.739  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.143   1.676   2.122  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.598   0.528   2.999  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.619  -0.113   2.317  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.983   0.597   0.983  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.243   2.111   1.235  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.396   2.444   1.963  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.035   2.698   2.029  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.103   2.648  -0.187  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.742   3.575  -0.667  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.015   1.911  -0.924  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.281   2.716  -0.917  0.00  0.00           C+0
HETATM   29  H   UNK     0      -5.877  -0.174  -0.141  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.904  -1.868  -0.670  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.611  -1.507   1.043  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.625  -2.560  -1.370  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.963  -3.680  -2.784  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.367  -2.848  -2.919  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.051  -0.825  -1.644  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.117   0.130   0.927  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.773   3.328  -0.296  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.168   1.865   0.572  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.004   3.639   2.188  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.441   4.160   1.589  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.110   1.542   3.022  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.135   2.861   3.659  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.368  -0.235   3.167  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.315   0.896   3.993  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.406  -1.176   2.143  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.477  -0.091   3.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.145   1.892   1.655  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.352   2.967   3.047  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.288   3.647   1.587  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.356   1.652  -1.931  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.153   3.711  -0.478  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.642   2.859  -1.941  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   21    3    6                                                  
CONECT    6   11    5    7                                                  
CONECT    7    8    6   32                                                  
CONECT    8    9    7   33                                                  
CONECT    9   10    8   34                                                  
CONECT   10   11    9   35                                                  
CONECT   11   10   12    6                                                  
CONECT   12   21   11   27   13                                             
CONECT   13   14   12   36   18                                             
CONECT   14   15   13   28                                                  
CONECT   15   16   14   37   38                                             
CONECT   16   17   15   39   40                                             
CONECT   17   18   16   41   42                                             
CONECT   18   17   24   13   19                                             
CONECT   19   20   18   43   44                                             
CONECT   20   21   19   45   46                                             
CONECT   21    5   22   12   20                                             
CONECT   22   21   24   25   23                                             
CONECT   23   22   47                                                       
CONECT   24   18   22   48   49                                             
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   28   12   25   50                                             
CONECT   28   14   27   51   52                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   27                                                            
CONECT   51   28                                                            
CONECT   52   28                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  116    0
END

RDKit          3D

52 58  0  0  0  0  0  0  0  0999 V2000
   -5.4338   -1.1617    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -1.1337   -0.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137   -0.2944    0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223    0.3907    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -0.2368    0.2254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322   -1.0421   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217   -2.1545   -1.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -2.8015   -2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -2.3340   -2.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369   -1.2077   -1.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.5781   -0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.6948    0.0059 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5130    1.0300    0.7518 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2359    1.8887   -0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3654    2.5961    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    3.2758    1.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906    2.3209    2.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1425    1.6756    2.1220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5976    0.5277    2.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.1130    2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833    0.5973    0.9830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2426    2.1112    1.2353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3960    2.4442    1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    2.6982    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033    2.6476   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424    3.5746   -0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149    1.9114   -0.9235 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2810    2.7160   -0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773   -0.1740   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9041   -1.8678   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113   -1.5073    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -2.5604   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9626   -3.6804   -2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -2.8476   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -0.8249   -1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    0.1296    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    3.3281   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    1.8649    0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042    3.6393    2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4408    4.1602    1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1100    1.5415    3.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    2.8606    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -0.2354    3.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146    0.8964    3.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4059   -1.1757    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774   -0.0913    3.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    1.8923    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    2.9669    3.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    3.6465    1.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    1.6517   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    3.7112   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420    2.8591   -1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  1
 17 16  1  0
 16 15  1  0
 15 14  1  0
 21  5  1  6
 18 24  1  0
 11 10  2  0
 21 22  1  0
 24 22  1  0
 13 14  1  0
 10  9  1  0
 12 21  1  0
 12 11  1  6
 11  6  1  0
 14 28  1  0
 28 27  1  0
 27 12  1  0
 12 13  1  0
 22 25  1  0
 21 20  1  0
 13 36  1  1
 20 19  1  0
  5  3  1  0
  3  2  1  0
 13 18  1  0
  2  1  1  0
  9  8  2  0
  3  4  2  0
  6  5  1  0
 22 23  1  1
  8  7  1  0
 25 26  2  0
  7  6  2  0
 27 25  1  0
 18 19  1  0
  9 34  1  0
  8 33  1  0
  7 32  1  0
 10 35  1  0
 20 45  1  0
 20 46  1  0
 19 43  1  0
 19 44  1  0
 17 41  1  0
 17 42  1  0
 16 39  1  0
 16 40  1  0
 15 37  1  0
 15 38  1  0
 24 48  1  0
 24 49  1  0
 28 51  1  0
 28 52  1  0
 27 50  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 47  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄N₂O₄

Average Mass

380.4440 Da

Monoisotopic Mass

380.17361 Da

IUPAC Name

methyl (1R,2S,3R,11S,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

Traditional Name

methyl (1R,2S,3R,11S,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=O)[C@@]3([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]5(C([H])([H])C([H])([H])[C@@]11N(C(=O)OC([H])([H])[H])C6=C([H])C([H])=C([H])C([H])=C6[C@@]31[C@@]45[H])C2([H])[H]

InChI Identifier

InChI=1S/C22H24N2O4/c1-28-18(26)24-15-6-3-2-5-13(15)22-14-11-23-10-4-7-19(17(22)23)8-9-21(22,24)20(27,12-19)16(14)25/h2-3,5-6,14,17,27H,4,7-12H2,1H3/t14-,17+,19-,20-,21-,22+/m1/s1

InChI Key

YROYAGSZNDUMIF-MQVQQYNVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Kopsia dasyrachis	Plant	KNApSAcK
Kopsia fruticosa	JEOL database	Glover, R. P., et al, Magn. Reson. Chem. 43, 483 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Aspidosperma alkaloid
Carbazole
Indolecarboxylic acid
Indolecarboxylic acid derivative
2,3-cyclopentanoindoline
Azaspirodecane
Quinolidine
Indole or derivatives
Indolizidine
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Cyclic alcohol
Carbamic acid ester
Pyrrolidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Ketone
Carbonic acid derivative
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Amine
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	0.9	ALOGPS
logP	1.57	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.07 m³·mol⁻¹	ChemAxon
Polarizability	39.69 Å³	ChemAxon
Number of Rings	7	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

16735868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20054949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Leng L, Zhou X, Liao Q, Wang F, Song H, Zhang D, Liu XY, Qin Y: Asymmetric Total Syntheses of Kopsia Indole Alkaloids. Angew Chem Int Ed Engl. 2017 Mar 20;56(13):3703-3707. doi: 10.1002/anie.201700831. Epub 2017 Feb 23. [PubMed:28230294 ]
Yap WS, Gan CY, Sim KS, Lim SH, Low YY, Kam TS: Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora. J Nat Prod. 2016 Jan 22;79(1):230-9. doi: 10.1021/acs.jnatprod.5b00992. Epub 2015 Dec 30. [PubMed:26717050 ]
Glover RP, Yoganathan K, Butler MS: NMR spectral assignments of three aspidofractinine alkaloids, kopsine, fruticosine and fruticosamine. Magn Reson Chem. 2005 Jun;43(6):483-5. doi: 10.1002/mrc.1580. [PubMed:15818570 ]
Glover, R. P., et al. (2005). Glover, R. P., et al, Magn. Reson. Chem. 43, 483 (2005). Mag. Reson. Chem..

Showing NP-Card for kopsine (NP0031116)

MOL for NP0031116 (kopsine)

3D MOL for NP0031116 (kopsine)

3D SDF for NP0031116 (kopsine)

3D-SDF for NP0031116 (kopsine)

PDB for NP0031116 (kopsine)

3D PDB for NP0031116 (kopsine)

SMILES for NP0031116 (kopsine)

INCHI for NP0031116 (kopsine)

Structure for NP0031116 (kopsine)

3D Structure for NP0031116 (kopsine)