NP-MRD: Showing NP-Card for 6-O-methylpretazettine (NP0026171)

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Record Information

Version

2.0

Created at

2021-06-19 18:06:06 UTC

Updated at

2021-06-29 23:51:33 UTC

NP-MRD ID

NP0026171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-methylpretazettine

Provided By

JEOL Database JEOL Logo

Description

6-O-methylpretazettine is found in Eucharis amazonica, Lycoris squamigera and Narcissus tazetta. 6-O-methylpretazettine was first documented in 2003 (Cabezas, F., et al.). Based on a literature review very few articles have been published on (3S,13bS)-3,8beta-Dimethoxy-5-methyl-3,4,4abeta,5,6,6abeta-hexahydro-8H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indole.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120063D          

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M  END

     RDKit          3D

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  Mrv1652306192120063D          

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  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  6  5  1  6  0  0  0
 21 44  1  1  0  0  0
  6 21  1  0  0  0  0
 17 38  1  1  0  0  0
 21 22  1  0  0  0  0
 13 14  1  0  0  0  0
 22  3  1  0  0  0  0
  2  1  1  0  0  0  0
  9 25  1  0  0  0  0
 14 15  1  0  0  0  0
 25 24  1  0  0  0  0
 19 20  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
  3 29  1  6  0  0  0
 11 33  1  0  0  0  0
  8 32  1  0  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
 13 34  1  6  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2OC([H])([H])OC2=C([H])C2=C1[C@]([H])(OC([H])([H])[H])O[C@@]1([H])C([H])([H])N(C([H])([H])[H])[C@@]3([H])C([H])([H])[C@]([H])(OC([H])([H])[H])C([H])=C([H])[C@@]213

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO5/c1-20-9-17-19(5-4-11(21-2)6-16(19)20)13-8-15-14(23-10-24-15)7-12(13)18(22-3)25-17/h4-5,7-8,11,16-18H,6,9-10H2,1-3H3/t11-,16+,17+,18-,19+/m1/s1

> <INCHI_KEY>
MWGLYQGPZVUKHO-HVEWUWHJSA-N

> <FORMULA>
C19H23NO5

> <MOLECULAR_WEIGHT>
345.395

> <EXACT_MASS>
345.157622845

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.245112166690376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11R,13R,16S,18S)-11,18-dimethoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,19-tetraene

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.747778225

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.966745523722374

> <JCHEM_POLAR_SURFACE_AREA>
49.39

> <JCHEM_REFRACTIVITY>
91.63640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11R,13R,16S,18S)-11,18-dimethoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,19-tetraene

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
   -2.9899   -4.2419   -3.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112   -3.7242   -3.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7412   -2.3269   -2.9101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3595   -1.8022   -3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824   -0.9452   -2.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -0.3924   -1.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6686   -0.7193    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285   -1.9345    0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -2.1541    1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539   -1.2316    2.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -0.0311    1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912    0.2412    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    1.5809   -0.3731 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6290    2.6177    0.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222    3.8815    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893    1.7551   -1.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    1.1431   -1.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6178    1.3961   -1.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751    0.3093   -1.6431 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    0.7976   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110   -0.7496   -0.8969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1813   -2.1273   -1.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3868   -1.6494    3.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255   -2.9445    3.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -3.2714    2.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905   -3.7288   -4.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -5.3023   -3.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853   -4.1532   -2.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -1.8110   -3.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.1314   -4.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787   -0.6111   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -2.7028    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132    0.6862    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.6434   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711    3.8619   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    4.1779   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    4.6237    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214    1.5114   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    1.3338   -3.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292    2.4027   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.5378   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982   -0.0220   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3953    1.2598    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -0.7196    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -2.9167   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -2.2820   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294   -2.9642    4.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -3.7065    3.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 10  1  0
  7 12  2  0
 10 11  2  0
 11 12  1  0
  4  5  2  0
  7  8  1  0
  7  6  1  0
 12 13  1  0
 13 16  1  0
 16 17  1  0
 17  6  1  0
  8  9  2  0
 21 19  1  0
 10  9  1  0
 17 18  1  0
 19 18  1  0
  4  3  1  0
  3  2  1  0
  6  5  1  6
 21 44  1  1
  6 21  1  0
 17 38  1  1
 21 22  1  0
 13 14  1  0
 22  3  1  0
  2  1  1  0
  9 25  1  0
 14 15  1  0
 25 24  1  0
 19 20  1  0
  4 30  1  0
  5 31  1  0
 22 45  1  0
 22 46  1  0
  3 29  1  6
 11 33  1  0
  8 32  1  0
 24 47  1  0
 24 48  1  0
 13 34  1  6
 18 39  1  0
 18 40  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 20 41  1  0
 20 42  1  0
 20 43  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      -2.990  -4.242  -3.563  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.711  -3.724  -3.222  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.741  -2.327  -2.910  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.360  -1.802  -3.168  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.282  -0.945  -2.358  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.301  -0.392  -1.054  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.669  -0.719   0.076  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.629  -1.935   0.777  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.579  -2.154   1.752  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.554  -1.232   2.043  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.640  -0.031   1.374  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.691   0.241   0.371  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.765   1.581  -0.373  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.629   2.618   0.602  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.022   3.882   0.087  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.789   1.755  -1.413  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.435   1.143  -1.036  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.618   1.396  -1.953  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.575   0.309  -1.643  0.00  0.00           N+0
HETATM   20  C   UNK     0      -3.708   0.798  -0.860  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.811  -0.750  -0.897  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.181  -2.127  -1.456  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.387  -1.649   3.033  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.825  -2.945   3.330  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.676  -3.271   2.523  0.00  0.00           O+0
HETATM   26  H   UNK     0      -3.390  -3.729  -4.442  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.876  -5.302  -3.804  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.685  -4.153  -2.724  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.423  -1.811  -3.598  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.122  -2.131  -4.085  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.279  -0.611  -2.640  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.105  -2.703   0.569  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.413   0.686   1.628  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.754   1.643  -0.846  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.071   3.862  -0.225  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.385   4.178  -0.751  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.912   4.624   0.882  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.721   1.511  -0.037  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.319   1.334  -3.006  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.029   2.403  -1.813  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.276   1.538  -1.435  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.398  -0.022  -0.632  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.395   1.260   0.083  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.074  -0.720   0.170  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.746  -2.917  -0.833  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.265  -2.282  -1.379  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.529  -2.964   4.386  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.596  -3.707   3.168  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   22   29                                             
CONECT    4    5    3   30                                                  
CONECT    5    4    6   31                                                  
CONECT    6    7   17    5   21                                             
CONECT    7   12    8    6                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   25                                                  
CONECT   10   23   11    9                                                  
CONECT   11   10   12   33                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   16   14   34                                             
CONECT   14   13   15                                                       
CONECT   15   14   35   36   37                                             
CONECT   16   13   17                                                       
CONECT   17   16    6   18   38                                             
CONECT   18   17   19   39   40                                             
CONECT   19   21   18   20                                                  
CONECT   20   19   41   42   43                                             
CONECT   21   19   44    6   22                                             
CONECT   22   21    3   45   46                                             
CONECT   23   24   10                                                       
CONECT   24   23   25   47   48                                             
CONECT   25    9   24                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    8                                                            
CONECT   33   11                                                            
CONECT   34   13                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

RDKit          3D

48 52  0  0  0  0  0  0  0  0999 V2000
   -2.9899   -4.2419   -3.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112   -3.7242   -3.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7412   -2.3269   -2.9101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3595   -1.8022   -3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824   -0.9452   -2.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -0.3924   -1.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6686   -0.7193    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285   -1.9345    0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -2.1541    1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539   -1.2316    2.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -0.0311    1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912    0.2412    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    1.5809   -0.3731 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6290    2.6177    0.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222    3.8815    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893    1.7551   -1.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    1.1431   -1.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6178    1.3961   -1.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751    0.3093   -1.6431 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7082    0.7976   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110   -0.7496   -0.8969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1813   -2.1273   -1.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3868   -1.6494    3.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255   -2.9445    3.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -3.2714    2.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905   -3.7288   -4.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -5.3023   -3.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853   -4.1532   -2.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -1.8110   -3.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.1314   -4.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787   -0.6111   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -2.7028    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132    0.6862    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.6434   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711    3.8619   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    4.1779   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    4.6237    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214    1.5114   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    1.3338   -3.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292    2.4027   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.5378   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982   -0.0220   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3953    1.2598    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -0.7196    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -2.9167   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -2.2820   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294   -2.9642    4.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -3.7065    3.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 10  1  0
  7 12  2  0
 10 11  2  0
 11 12  1  0
  4  5  2  0
  7  8  1  0
  7  6  1  0
 12 13  1  0
 13 16  1  0
 16 17  1  0
 17  6  1  0
  8  9  2  0
 21 19  1  0
 10  9  1  0
 17 18  1  0
 19 18  1  0
  4  3  1  0
  3  2  1  0
  6  5  1  6
 21 44  1  1
  6 21  1  0
 17 38  1  1
 21 22  1  0
 13 14  1  0
 22  3  1  0
  2  1  1  0
  9 25  1  0
 14 15  1  0
 25 24  1  0
 19 20  1  0
  4 30  1  0
  5 31  1  0
 22 45  1  0
 22 46  1  0
  3 29  1  6
 11 33  1  0
  8 32  1  0
 24 47  1  0
 24 48  1  0
 13 34  1  6
 18 39  1  0
 18 40  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3S,13BS)-3,8b-Dimethoxy-5-methyl-3,4,4abeta,5,6,6abeta-hexahydro-8H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indole	Generator
(3S,13BS)-3,8Β-dimethoxy-5-methyl-3,4,4abeta,5,6,6abeta-hexahydro-8H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indole	Generator

Chemical Formula

C₁₉H₂₃NO₅

Average Mass

345.3950 Da

Monoisotopic Mass

345.15762 Da

IUPAC Name

(1S,11R,13R,16S,18S)-11,18-dimethoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,19-tetraene

Traditional Name

(1S,11R,13R,16S,18S)-11,18-dimethoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,19-tetraene

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC([H])([H])OC2=C([H])C2=C1[C@]([H])(OC([H])([H])[H])O[C@@]1([H])C([H])([H])N(C([H])([H])[H])[C@@]3([H])C([H])([H])[C@]([H])(OC([H])([H])[H])C([H])=C([H])[C@@]213

InChI Identifier

InChI=1S/C19H23NO5/c1-20-9-17-19(5-4-11(21-2)6-16(19)20)13-8-15-14(23-10-24-15)7-12(13)18(22-3)25-17/h4-5,7-8,11,16-18H,6,9-10H2,1-3H3/t11-,16+,17+,18-,19+/m1/s1

InChI Key

MWGLYQGPZVUKHO-HVEWUWHJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Eucharis amazonica	JEOL database	Cabezas, F., et al, Chem. Pharm. Bull. 51, 315 (2003)
Lycoris squamigera	LOTUS Database	35616633
Narcissus tazetta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Tazettine-type amaryllidaceae alkaloids

Direct Parent

Tazettine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Tazettine alkaloid skeleton
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Indole or derivatives
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Acetal
Oxacycle
Ether
Dialkyl ether
Azacycle
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	1.9	ALOGPS
logP	1.75	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.64 m³·mol⁻¹	ChemAxon
Polarizability	37.25 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

9101269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10926024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cabezas, F., et al. (2003). Cabezas, F., et al, Chem. Pharm. Bull. 51, 315 (2003). Chem. Pharm. Bull..

Showing NP-Card for 6-O-methylpretazettine (NP0026171)

MOL for NP0026171 (6-O-methylpretazettine)

3D MOL for NP0026171 (6-O-methylpretazettine)

3D SDF for NP0026171 (6-O-methylpretazettine)

3D-SDF for NP0026171 (6-O-methylpretazettine)

PDB for NP0026171 (6-O-methylpretazettine)

3D PDB for NP0026171 (6-O-methylpretazettine)

SMILES for NP0026171 (6-O-methylpretazettine)

INCHI for NP0026171 (6-O-methylpretazettine)

Structure for NP0026171 (6-O-methylpretazettine)

3D Structure for NP0026171 (6-O-methylpretazettine)