NP-MRD: Showing NP-Card for alstophyllal (NP0027140)

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Record Information

Version

2.0

Created at

2021-06-19 18:50:46 UTC

Updated at

2021-06-29 23:53:05 UTC

NP-MRD ID

NP0027140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alstophyllal

Provided By

JEOL Database JEOL Logo

Description

alstophyllal is found in Alstonia macrophylla. alstophyllal was first documented in 2004 (PMID: 15104482). Based on a literature review very few articles have been published on Alstophyllal.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120503D          

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     RDKit          3D

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    3.6595    3.6321   -0.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    0.7962    0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616    2.4592    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6470    0.9074    2.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398   -0.1345    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.2309    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0525    2.7670    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2994    4.0219    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
 23 15  1  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
  3 12  2  0  0  0  0
  7  8  2  0  0  0  0
  7  6  1  0  0  0  0
 11  9  1  0  0  0  0
 23 22  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9  8  1  0  0  0  0
 19 20  1  0  0  0  0
 11  6  2  0  0  0  0
 16 17  1  0  0  0  0
 15 40  1  1  0  0  0
 11 12  1  0  0  0  0
 23 47  1  1  0  0  0
  7 25  1  0  0  0  0
 13 37  1  6  0  0  0
  8 13  1  0  0  0  0
 24 48  1  1  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 24  1  0  0  0  0
  9 10  1  0  0  0  0
 24 25  1  0  0  0  0
 17 18  2  0  0  0  0
  6  5  1  0  0  0  0
 17 41  1  0  0  0  0
 13 14  1  0  0  0  0
  3  2  1  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
  5 32  1  0  0  0  0
  4 31  1  0  0  0  0
 12 36  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)C1=C(OC([H])([H])[C@@]2([H])[C@@]3([H])N(C([H])([H])[H])[C@]([H])(C4=C(C5=C(C([H])=C(OC([H])([H])[H])C([H])=C5[H])N4C([H])([H])[H])C3([H])[H])C([H])([H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3/c1-12-17(10-25)15-8-21-22-16(9-20(23(21)2)18(15)11-27-12)14-6-5-13(26-4)7-19(14)24(22)3/h5-7,10,15,18,20-21H,8-9,11H2,1-4H3/t15-,18+,20-,21-/m0/s1

> <INCHI_KEY>
OKOHMBRGHIAYBH-MTOHEIAKSA-N

> <FORMULA>
C22H26N2O3

> <MOLECULAR_WEIGHT>
366.461

> <EXACT_MASS>
366.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.12431762912267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,13R,18R)-6-methoxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
1.7964189713333338

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.602058291048934

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
106.57229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13R,18R)-6-methoxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.9983   -4.1494    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -4.1181    1.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0530   -3.0509    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -3.0970    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -2.0824    2.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348   -0.9942    1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.1716    1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155    0.9011    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    0.2057   -0.2761 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090    0.5799   -1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -0.9552    0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -1.9757    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    2.1972   -0.4217 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3970    1.9429   -1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534    1.0927   -1.3713 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5914    1.0686   -2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1633    0.2589   -3.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.3368   -3.7817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.6959   -2.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7838    1.6594   -3.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2378    2.4426   -1.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    2.7970   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3936    1.5913   -0.1091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4466    1.9385    1.0707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8844    0.6590    1.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071    2.8773    0.5729 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    3.4850    1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -4.1860   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -3.3007    0.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -5.0647    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -3.9376    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105   -2.1394    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658    1.4841   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -0.2387   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    0.7583   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -1.9099   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2869    2.8639   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.4473   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    2.9098   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395    0.0585   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8610    0.2183   -4.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6765    2.2443   -3.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    0.6341   -3.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3589    2.0889   -4.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7993    3.1732    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595    3.6321   -0.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    0.7962    0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616    2.4592    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6470    0.9074    2.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398   -0.1345    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.2309    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0525    2.7670    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2994    4.0219    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 23 15  1  0
  5  4  2  0
  4  3  1  0
  3 12  2  0
  7  8  2  0
  7  6  1  0
 11  9  1  0
 23 22  1  0
 15 16  1  0
 16 19  2  0
 19 21  1  0
 21 22  1  0
  9  8  1  0
 19 20  1  0
 11  6  2  0
 16 17  1  0
 15 40  1  1
 11 12  1  0
 23 47  1  1
  7 25  1  0
 13 37  1  6
  8 13  1  0
 24 48  1  1
 13 26  1  0
 26 27  1  0
 26 24  1  0
  9 10  1  0
 24 25  1  0
 17 18  2  0
  6  5  1  0
 17 41  1  0
 13 14  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
  5 32  1  0
  4 31  1  0
 12 36  1  0
 25 49  1  0
 25 50  1  0
 14 38  1  0
 14 39  1  0
 22 45  1  0
 22 46  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
  1 28  1  0
  1 29  1  0
  1 30  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      -3.998  -4.149   0.505  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.908  -4.118   1.417  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.053  -3.051   1.324  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.981  -3.097   2.215  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.017  -2.082   2.244  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.135  -0.994   1.360  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.635   0.172   1.125  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.016   0.901   0.130  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.093   0.206  -0.276  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.009   0.580  -1.331  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.215  -0.955   0.474  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.187  -1.976   0.438  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.539   2.197  -0.422  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.397   1.943  -1.673  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.653   1.093  -1.371  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.591   1.069  -2.560  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.163   0.259  -3.736  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.093  -0.337  -3.782  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.786   1.696  -2.555  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.784   1.659  -3.679  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.238   2.443  -1.482  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.253   2.797  -0.504  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.394   1.591  -0.109  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.447   1.938   1.071  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.884   0.659   1.778  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.407   2.877   0.573  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.634   3.485   1.655  0.00  0.00           C+0
HETATM   28  H   UNK     0      -3.647  -4.186  -0.531  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.671  -3.301   0.666  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.567  -5.065   0.695  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.888  -3.938   2.898  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.811  -2.139   2.944  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.666   1.484  -1.836  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.057  -0.239  -2.054  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.991   0.758  -0.885  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.008  -1.910  -0.264  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.287   2.864  -0.697  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.789   1.447  -2.440  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.693   2.910  -2.104  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.340   0.059  -1.176  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.861   0.218  -4.587  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.676   2.244  -3.431  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.113   0.634  -3.876  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.359   2.089  -4.592  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.799   3.173   0.368  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.660   3.632  -0.895  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.082   0.796   0.213  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.062   2.459   1.818  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.647   0.907   2.820  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.640  -0.135   1.797  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.060   4.231   1.251  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.053   2.767   2.242  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.299   4.022   2.340  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3    4   12    2                                                  
CONECT    4    5    3   31                                                  
CONECT    5    4    6   32                                                  
CONECT    6    7   11    5                                                  
CONECT    7    8    6   25                                                  
CONECT    8    7    9   13                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9   33   34   35                                             
CONECT   11    9    6   12                                                  
CONECT   12    3   11   36                                                  
CONECT   13   37    8   26   14                                             
CONECT   14   15   13   38   39                                             
CONECT   15   14   23   16   40                                             
CONECT   16   15   19   17                                                  
CONECT   17   16   18   41                                                  
CONECT   18   17                                                            
CONECT   19   16   21   20                                                  
CONECT   20   19   42   43   44                                             
CONECT   21   19   22                                                       
CONECT   22   23   21   45   46                                             
CONECT   23   15   22   47   24                                             
CONECT   24   48   26   25   23                                             
CONECT   25    7   24   49   50                                             
CONECT   26   13   27   24                                                  
CONECT   27   26   51   52   53                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

RDKit          3D

53 57  0  0  0  0  0  0  0  0999 V2000
   -3.9983   -4.1494    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -4.1181    1.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0530   -3.0509    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -3.0970    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -2.0824    2.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348   -0.9942    1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.1716    1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155    0.9011    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    0.2057   -0.2761 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090    0.5799   -1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -0.9552    0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -1.9757    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    2.1972   -0.4217 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3970    1.9429   -1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534    1.0927   -1.3713 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5914    1.0686   -2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1633    0.2589   -3.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.3368   -3.7817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.6959   -2.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7838    1.6594   -3.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2378    2.4426   -1.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    2.7970   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3936    1.5913   -0.1091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4466    1.9385    1.0707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8844    0.6590    1.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071    2.8773    0.5729 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    3.4850    1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -4.1860   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -3.3007    0.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -5.0647    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -3.9376    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105   -2.1394    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658    1.4841   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -0.2387   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    0.7583   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -1.9099   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2869    2.8639   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.4473   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    2.9098   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395    0.0585   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8610    0.2183   -4.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6765    2.2443   -3.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    0.6341   -3.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3589    2.0889   -4.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7993    3.1732    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595    3.6321   -0.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    0.7962    0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616    2.4592    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6470    0.9074    2.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398   -0.1345    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.2309    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0525    2.7670    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2994    4.0219    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 23 15  1  0
  5  4  2  0
  4  3  1  0
  3 12  2  0
  7  8  2  0
  7  6  1  0
 11  9  1  0
 23 22  1  0
 15 16  1  0
 16 19  2  0
 19 21  1  0
 21 22  1  0
  9  8  1  0
 19 20  1  0
 11  6  2  0
 16 17  1  0
 15 40  1  1
 11 12  1  0
 23 47  1  1
  7 25  1  0
 13 37  1  6
  8 13  1  0
 24 48  1  1
 13 26  1  0
 26 27  1  0
 26 24  1  0
  9 10  1  0
 24 25  1  0
 17 18  2  0
  6  5  1  0
 17 41  1  0
 13 14  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
  5 32  1  0
  4 31  1  0
 12 36  1  0
 25 49  1  0
 25 50  1  0
 14 38  1  0
 14 39  1  0
 22 45  1  0
 22 46  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₃

Average Mass

366.4610 Da

Monoisotopic Mass

366.19434 Da

IUPAC Name

(1S,12S,13R,18R)-6-methoxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde

Traditional Name

(1S,12S,13R,18R)-6-methoxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H]C(=O)C1=C(OC([H])([H])[C@@]2([H])[C@@]3([H])N(C([H])([H])[H])[C@]([H])(C4=C(C5=C(C([H])=C(OC([H])([H])[H])C([H])=C5[H])N4C([H])([H])[H])C3([H])[H])C([H])([H])[C@@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H26N2O3/c1-12-17(10-25)15-8-21-22-16(9-20(23(21)2)18(15)11-27-12)14-6-5-13(26-4)7-19(14)24(22)3/h5-7,10,15,18,20-21H,8-9,11H2,1-4H3/t15-,18+,20-,21-/m0/s1

InChI Key

OKOHMBRGHIAYBH-MTOHEIAKSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia macrophylla	JEOL database	Kam, T.-S., et al, J. Nat. Prod. 67, 547 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Beta-carboline
Pyridoindole
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
Substituted pyrrole
Piperidine
N-methylpyrrole
Pyrrole
Heteroaromatic compound
Vinylogous ester
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Aldehyde
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Amine
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
logP	2.71	ALOGPS
logP	1.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.57 m³·mol⁻¹	ChemAxon
Polarizability	41.12 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

10187623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21577244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kam TS, Choo YM: New indole alkaloids from Alstonia macrophylla. J Nat Prod. 2004 Apr;67(4):547-52. doi: 10.1021/np034041v. [PubMed:15104482 ]
Kam, T.-S., et al. (2004). Kam, T.-S., et al, J. Nat. Prod. 67, 547 (2004). J. Nat. Prod..

Showing NP-Card for alstophyllal (NP0027140)

MOL for NP0027140 (alstophyllal)

3D MOL for NP0027140 (alstophyllal)

3D SDF for NP0027140 (alstophyllal)

3D-SDF for NP0027140 (alstophyllal)

PDB for NP0027140 (alstophyllal)

3D PDB for NP0027140 (alstophyllal)

SMILES for NP0027140 (alstophyllal)

INCHI for NP0027140 (alstophyllal)

Structure for NP0027140 (alstophyllal)

3D Structure for NP0027140 (alstophyllal)