NP-MRD: Showing NP-Card for macrogentine (NP0029881)

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Record Information

Version

2.0

Created at

2021-06-19 21:23:26 UTC

Updated at

2021-06-29 23:57:31 UTC

NP-MRD ID

NP0029881

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macrogentine

Provided By

JEOL Database JEOL Logo

Description

macrogentine is found in Alstonia angustifolia, Alstonia angustifolia var.latifolia, Alstonia macrophylla and Alstonia muelleriana. macrogentine was first documented in 2017 (PMID: 28875520). Based on a literature review very few articles have been published on Macrogentine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123233D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192123233D          

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   -0.8750    3.6440    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -0.0420   -2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.4647   -3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.2481   -3.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5685    1.4433   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863    3.1881   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8220    2.9509   -2.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    3.7388   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1  0  0  0
 14 12  1  0  0  0  0
 22 23  1  0  0  0  0
  4  2  1  0  0  0  0
 23 24  1  0  0  0  0
  2  3  2  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
 22 46  1  6  0  0  0
 24 25  1  0  0  0  0
  5 32  1  1  0  0  0
  7  8  1  0  0  0  0
  7 35  1  1  0  0  0
 22  9  1  0  0  0  0
  9  8  1  0  0  0  0
 12 13  2  0  0  0  0
  7 11  1  0  0  0  0
 14 15  1  0  0  0  0
 22  5  1  0  0  0  0
  9 36  1  6  0  0  0
 21 16  2  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 10  1  0  0  0  0
 18 19  1  0  0  0  0
 16 14  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  8 25  1  0  0  0  0
  5  4  1  0  0  0  0
 21 11  1  0  0  0  0
 25 26  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 25 49  1  1  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(C([H])=C1[H])[C@]1(C(=O)N2C([H])([H])[H])C([H])([H])[C@]2([H])N3[C@@]1([H])C([H])([H])[C@@]([H])(C([H])([H])C(=O)C([H])([H])[H])[C@@]2([H])C([H])([H])O[C@]3([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-12(24)8-14-9-19-21(10-18-15(14)11-26-13(2)23(18)19)16-6-4-5-7-17(16)22(3)20(21)25/h4-7,13-15,18-19H,8-11H2,1-3H3/t13-,14-,15-,18+,19+,21-/m1/s1

> <INCHI_KEY>
FUFCKBIZSJGNAI-RKBASDMCSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.632878258471784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2'S,3R,4'S,7'S,9'R)-1,9'-dimethyl-2'-(2-oxopropyl)-1,2-dihydro-10'-oxa-8'-azaspiro[indole-3,5'-tricyclo[5.4.0.0^{4,8}]undecane]-2-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.481517444333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.499909738090285

> <JCHEM_PKA_STRONGEST_BASIC>
7.524043522162603

> <JCHEM_POLAR_SURFACE_AREA>
49.85000000000001

> <JCHEM_REFRACTIVITY>
98.13020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,3R,4'S,7'S,9'R)-1,9'-dimethyl-2'-(2-oxopropyl)-10'-oxa-8'-azaspiro[indole-3,5'-tricyclo[5.4.0.0^{4,8}]undecane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    1.0931   -3.8380   -2.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -2.9017   -2.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669   -2.4876   -4.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -2.4461   -1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -1.1715   -1.2218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5697   -0.8965   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.5180    0.5626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4906    1.5580   -0.4907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535    1.3557   -1.2496 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8041    1.2320   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8351    1.1207 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6617   -0.3195    1.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -1.4232    1.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    0.1303    3.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558   -0.6572    4.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    1.4588    3.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    2.2515    4.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934    3.5705    4.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127    4.0671    3.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4791    3.2518    2.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342    1.9402    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190    0.0903   -2.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6086    0.3631   -3.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935    0.5380   -2.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060    1.5756   -1.2976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8967    2.9427   -1.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -4.7450   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741   -4.1157   -3.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -3.3452   -1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -2.3224   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -3.2621   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -1.3865   -0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6084   -1.0310   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -1.6563    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.6761    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    2.2213   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055    2.1979    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    0.5068   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742   -1.6688    3.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897   -0.1874    4.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.7196    5.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.8758    5.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369    4.2206    5.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    5.0970    3.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750    3.6440    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -0.0420   -2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.4647   -3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.2481   -3.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5685    1.4433   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863    3.1881   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8220    2.9509   -2.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    3.7388   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1
 14 12  1  0
 22 23  1  0
  4  2  1  0
 23 24  1  0
  2  3  2  0
  5  6  1  0
  2  1  1  0
  6  7  1  0
 22 46  1  6
 24 25  1  0
  5 32  1  1
  7  8  1  0
  7 35  1  1
 22  9  1  0
  9  8  1  0
 12 13  2  0
  7 11  1  0
 14 15  1  0
 22  5  1  0
  9 36  1  6
 21 16  2  0
  9 10  1  0
 16 17  1  0
 17 18  2  0
 11 10  1  0
 18 19  1  0
 16 14  1  0
 19 20  2  0
 20 21  1  0
  8 25  1  0
  5  4  1  0
 21 11  1  0
 25 26  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  1
  4 30  1  0
  4 31  1  0
  6 33  1  0
  6 34  1  0
 10 37  1  0
 10 38  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.093  -3.838  -2.411  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.037  -2.902  -2.938  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.067  -2.488  -4.097  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.031  -2.446  -1.965  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.609  -1.172  -1.222  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.570  -0.897  -0.041  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.410   0.518   0.563  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.491   1.558  -0.491  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.254   1.356  -1.250  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.804   1.232  -0.135  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.001   0.835   1.121  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.662  -0.320   1.923  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.974  -1.423   1.500  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.865   0.130   3.228  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.456  -0.657   4.279  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.469   1.459   3.380  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.542   2.252   4.512  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.093   3.571   4.418  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.413   4.067   3.207  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.479   3.252   2.074  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.034   1.940   2.172  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.419   0.090  -2.118  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.609   0.363  -3.042  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.793   0.538  -2.272  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.706   1.576  -1.298  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.897   2.943  -1.960  0.00  0.00           C+0
HETATM   27  H   UNK     0       0.621  -4.745  -2.026  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.774  -4.116  -3.221  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.664  -3.345  -1.621  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.974  -2.322  -2.506  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.202  -3.262  -1.252  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.379  -1.387  -0.802  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.608  -1.031  -0.368  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.427  -1.656   0.737  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.184   0.676   1.323  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.020   2.221  -1.881  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.306   2.198   0.005  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.583   0.507  -0.394  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.674  -1.669   3.925  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.390  -0.187   4.601  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.760  -0.720   5.121  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.935   1.876   5.449  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.137   4.221   5.289  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.758   5.097   3.150  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.875   3.644   1.142  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.481  -0.042  -2.731  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.778  -0.465  -3.735  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.435   1.248  -3.665  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.568   1.443  -0.633  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.086   3.188  -2.653  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.822   2.951  -2.546  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.956   3.739  -1.210  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    2    5   30   31                                             
CONECT    5    6   32   22    4                                             
CONECT    6    5    7   33   34                                             
CONECT    7    6    8   35   11                                             
CONECT    8    7    9   25                                                  
CONECT    9   22    8   36   10                                             
CONECT   10    9   11   37   38                                             
CONECT   11   12    7   10   21                                             
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   39   40   41                                             
CONECT   16   21   17   14                                                  
CONECT   17   16   18   42                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   44                                                  
CONECT   20   19   21   45                                                  
CONECT   21   16   20   11                                                  
CONECT   22   23   46    9    5                                             
CONECT   23   22   24   47   48                                             
CONECT   24   23   25                                                       
CONECT   25   24    8   26   49                                             
CONECT   26   25   50   51   52                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
    1.0931   -3.8380   -2.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -2.9017   -2.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669   -2.4876   -4.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -2.4461   -1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -1.1715   -1.2218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5697   -0.8965   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.5180    0.5626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4906    1.5580   -0.4907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535    1.3557   -1.2496 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8041    1.2320   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8351    1.1207 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6617   -0.3195    1.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -1.4232    1.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    0.1303    3.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558   -0.6572    4.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    1.4588    3.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    2.2515    4.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934    3.5705    4.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127    4.0671    3.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4791    3.2518    2.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342    1.9402    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190    0.0903   -2.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6086    0.3631   -3.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935    0.5380   -2.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060    1.5756   -1.2976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8967    2.9427   -1.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -4.7450   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741   -4.1157   -3.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -3.3452   -1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -2.3224   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -3.2621   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -1.3865   -0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6084   -1.0310   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -1.6563    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.6761    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    2.2213   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055    2.1979    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    0.5068   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742   -1.6688    3.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897   -0.1874    4.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -0.7196    5.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.8758    5.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369    4.2206    5.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    5.0970    3.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750    3.6440    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -0.0420   -2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.4647   -3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.2481   -3.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5685    1.4433   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863    3.1881   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8220    2.9509   -2.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    3.7388   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1
 14 12  1  0
 22 23  1  0
  4  2  1  0
 23 24  1  0
  2  3  2  0
  5  6  1  0
  2  1  1  0
  6  7  1  0
 22 46  1  6
 24 25  1  0
  5 32  1  1
  7  8  1  0
  7 35  1  1
 22  9  1  0
  9  8  1  0
 12 13  2  0
  7 11  1  0
 14 15  1  0
 22  5  1  0
  9 36  1  6
 21 16  2  0
  9 10  1  0
 16 17  1  0
 17 18  2  0
 11 10  1  0
 18 19  1  0
 16 14  1  0
 19 20  2  0
 20 21  1  0
  8 25  1  0
  5  4  1  0
 21 11  1  0
 25 26  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  1
  4 30  1  0
  4 31  1  0
  6 33  1  0
  6 34  1  0
 10 37  1  0
 10 38  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

(1'R,2'S,3R,4'S,7'S,9'R)-1,9'-dimethyl-2'-(2-oxopropyl)-1,2-dihydro-10'-oxa-8'-azaspiro[indole-3,5'-tricyclo[5.4.0.0^{4,8}]undecane]-2-one

Traditional Name

(1'R,2'S,3R,4'S,7'S,9'R)-1,9'-dimethyl-2'-(2-oxopropyl)-10'-oxa-8'-azaspiro[indole-3,5'-tricyclo[5.4.0.0^{4,8}]undecane]-2-one

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(C([H])=C1[H])[C@]1(C(=O)N2C([H])([H])[H])C([H])([H])[C@]2([H])N3[C@@]1([H])C([H])([H])[C@@]([H])(C([H])([H])C(=O)C([H])([H])[H])[C@@]2([H])C([H])([H])O[C@]3([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H26N2O3/c1-12(24)8-14-9-19-21(10-18-15(14)11-26-13(2)23(18)19)16-6-4-5-7-17(16)22(3)20(21)25/h4-7,13-15,18-19H,8-11H2,1-3H3/t13-,14-,15-,18+,19+,21-/m1/s1

InChI Key

FUFCKBIZSJGNAI-RKBASDMCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia angustifolia	Plant	KNApSAcK
Alstonia angustifolia var.latifolia	Plant	KNApSAcK
Alstonia macrophylla	LOTUS Database	35616633
Alstonia muelleriana	JEOL database	Kam, T.-S., et al, Tetrahedron 56, 6143 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
1,3-oxazinane
Oxazinane
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Hemiaminal
Ketone
Lactam
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
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	1.79	ALOGPS
logP	1.48	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.5	ChemAxon
pKa (Strongest Basic)	7.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.85 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.13 m³·mol⁻¹	ChemAxon
Polarizability	38.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

10238242

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15884897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stephen MR, Rahman MT, Tiruveedhula VVNPB, Fonseca GO, Deschamps JR, Cook JM: Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine. Chemistry. 2017 Nov 7;23(62):15805-15819. doi: 10.1002/chem.201703572. Epub 2017 Oct 18. [PubMed:28875520 ]
Kam, T.-S., et al. (2000). Kam, T.-S., et al, Tetrahedron 56, 6143 (2000). Tetrahedron.

Showing NP-Card for macrogentine (NP0029881)

MOL for NP0029881 (macrogentine)

3D MOL for NP0029881 (macrogentine)

3D SDF for NP0029881 (macrogentine)

3D-SDF for NP0029881 (macrogentine)

PDB for NP0029881 (macrogentine)

3D PDB for NP0029881 (macrogentine)

SMILES for NP0029881 (macrogentine)

INCHI for NP0029881 (macrogentine)

Structure for NP0029881 (macrogentine)

3D Structure for NP0029881 (macrogentine)