NP-MRD: Showing NP-Card for R(-)-canadaline (NP0037942)

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Record Information

Version

2.0

Created at

2021-06-20 20:45:13 UTC

Updated at

2021-06-30 00:10:26 UTC

NP-MRD ID

NP0037942

Secondary Accession Numbers

None

Natural Product Identification

Common Name

R(-)-canadaline

Provided By

JEOL Database JEOL Logo

Description

CANADALINE belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. R(-)-canadaline is found in Corydalis cava and Hydrastis canadensis L. . R(-)-canadaline was first documented in 2001 (PMID: 11509983). Based on a literature review a small amount of articles have been published on CANADALINE (PMID: 21615017) (PMID: 14640583) (PMID: 12898417) (PMID: 12852562).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122453D          

 50 53  0  0  0  0            999 V2000
    5.2530    4.3359   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170    3.9633   -3.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    3.2269   -3.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4348    2.7193   -1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689    2.0080   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.7904   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    1.0160   -0.7041 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0961   -0.5008   -1.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.3840   -1.4178    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222   -2.2531    1.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345   -2.5727    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750   -2.0097    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -2.3986    1.1921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6819   -1.4945    0.5287 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.5125   -2.3643   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5356    3.4703   -4.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    2.8912   -5.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    5.2530    4.3359   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202122453D          

 50 53  0  0  0  0            999 V2000
    5.2530    4.3359   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170    3.9633   -3.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    3.2269   -3.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6879    1.8857   -5.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  9  2  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
  7  6  1  0  0  0  0
  8 17  1  0  0  0  0
  6 22  2  0  0  0  0
 17 16  1  0  0  0  0
 22 25  1  0  0  0  0
 16 15  1  0  0  0  0
 25  3  2  0  0  0  0
 11 12  1  0  0  0  0
  3  4  1  0  0  0  0
 11 10  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
 10  9  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 14 13  1  0  0  0  0
 23 47  1  0  0  0  0
 13 12  2  0  0  0  0
 25 26  1  0  0  0  0
 12 19  1  0  0  0  0
 26 27  1  0  0  0  0
 19 20  1  0  0  0  0
  3  2  1  0  0  0  0
 20 21  1  0  0  0  0
  2  1  1  0  0  0  0
 21 11  1  0  0  0  0
  8 35  1  6  0  0  0
 10 36  1  0  0  0  0
 13 37  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
 27 48  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  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>
NP0037942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)C1=C(C([H])=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])[C@@]1([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C2=C1C([H])=C1OC([H])([H])OC1=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(22)8-13-4-5-18(24-2)21(25-3)16(13)11-23/h4-5,9-11,17H,6-8,12H2,1-3H3/t17-/m1/s1

> <INCHI_KEY>
ROAHDZJDHGLGBA-QGZVFWFLSA-N

> <FORMULA>
C21H23NO5

> <MOLECULAR_WEIGHT>
369.417

> <EXACT_MASS>
369.157622845

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.93698933535666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dimethoxy-6-{[(5R)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl}benzaldehyde

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.047825762666667

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.071382851570877

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
102.22540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dimethoxy-6-{[(5R)-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl}benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    5.2530    4.3359   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170    3.9633   -3.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    3.2269   -3.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4348    2.7193   -1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689    2.0080   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.7904   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    1.0160   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -0.5008   -1.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -1.1441   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -0.8523   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840   -1.4178    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222   -2.2531    1.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345   -2.5727    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750   -2.0097    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -2.3986    1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -1.4945    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -1.1823   -0.8803 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -2.3643   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2560   -2.7066    1.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2626   -2.0560    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -1.2367   -0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8808    2.2947   -2.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543    2.1372   -3.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    1.4313   -3.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    2.9847   -3.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    3.4703   -4.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    2.8912   -5.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7900    4.9682   -3.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744    3.4564   -2.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945    4.9228   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056    2.8551   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330    1.6148   -0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    1.1415    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    1.5058   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742   -0.5791   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -0.1964   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -3.2481    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -2.3590    2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -3.4373    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513   -0.5575    1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -1.9520    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -2.8446   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -3.1110   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446   -2.0752   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9024   -2.8244    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8774   -1.4251    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    2.6942   -4.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977    2.8104   -6.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670    3.5487   -6.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6879    1.8857   -5.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  9  2  0
 17 18  1  0
 14 15  1  0
  8  7  1  0
  9  8  1  0
  7  6  1  0
  8 17  1  0
  6 22  2  0
 17 16  1  0
 22 25  1  0
 16 15  1  0
 25  3  2  0
 11 12  1  0
  3  4  1  0
 11 10  2  0
  4  5  2  0
  5  6  1  0
 10  9  1  0
 22 23  1  0
 23 24  2  0
 14 13  1  0
 23 47  1  0
 13 12  2  0
 25 26  1  0
 12 19  1  0
 26 27  1  0
 19 20  1  0
  3  2  1  0
 20 21  1  0
  2  1  1  0
 21 11  1  0
  8 35  1  6
 10 36  1  0
 13 37  1  0
 16 40  1  0
 16 41  1  0
 15 38  1  0
 15 39  1  0
 20 45  1  0
 20 46  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
  7 33  1  0
  7 34  1  0
  4 31  1  0
  5 32  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
  1 28  1  0
  1 29  1  0
  1 30  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       5.253   4.336  -3.195  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.017   3.963  -3.791  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.143   3.227  -3.035  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.435   2.719  -1.770  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.469   2.008  -1.055  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.179   1.790  -1.571  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.200   1.016  -0.704  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.096  -0.501  -1.048  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.038  -1.144  -0.246  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.372  -0.852  -0.591  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.384  -1.418   0.154  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.122  -2.253   1.211  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.835  -2.573   1.581  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.775  -2.010   0.848  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.640  -2.399   1.192  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.682  -1.494   0.529  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.411  -1.182  -0.880  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.513  -2.364  -1.736  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.256  -2.707   1.810  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.263  -2.056   1.007  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.717  -1.237  -0.046  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.881   2.295  -2.854  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.454   2.137  -3.495  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.351   1.431  -3.050  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.871   2.985  -3.587  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.536   3.470  -4.833  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.328   2.891  -5.872  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.790   4.968  -3.909  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.874   3.456  -2.998  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.095   4.923  -2.285  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.406   2.855  -1.305  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.733   1.615  -0.074  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.480   1.141   0.351  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.780   1.506  -0.754  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.174  -0.579  -2.110  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.610  -0.196  -1.425  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.655  -3.248   2.410  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.780  -2.359   2.279  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.797  -3.437   0.876  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.751  -0.558   1.095  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.675  -1.952   0.626  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.490  -2.845  -1.612  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.736  -3.111  -1.540  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.445  -2.075  -2.791  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.902  -2.824   0.557  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.877  -1.425   1.659  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.623   2.694  -4.430  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.698   2.810  -6.763  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.167   3.549  -6.118  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.688   1.886  -5.624  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   25    4    2                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6   32                                                  
CONECT    6    7   22    5                                                  
CONECT    7    8    6   33   34                                             
CONECT    8    7    9   17   35                                             
CONECT    9   14    8   10                                                  
CONECT   10   11    9   36                                                  
CONECT   11   12   10   21                                                  
CONECT   12   11   13   19                                                  
CONECT   13   14   12   37                                                  
CONECT   14    9   15   13                                                  
CONECT   15   14   16   38   39                                             
CONECT   16   17   15   40   41                                             
CONECT   17   18    8   16                                                  
CONECT   18   17   42   43   44                                             
CONECT   19   12   20                                                       
CONECT   20   19   21   45   46                                             
CONECT   21   20   11                                                       
CONECT   22    6   25   23                                                  
CONECT   23   22   24   47                                                  
CONECT   24   23                                                            
CONECT   25   22    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   48   49   50                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   13                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   23                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
    5.2530    4.3359   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170    3.9633   -3.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    3.2269   -3.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4348    2.7193   -1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689    2.0080   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.7904   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    1.0160   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -0.5008   -1.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -1.1441   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722   -0.8523   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840   -1.4178    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222   -2.2531    1.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345   -2.5727    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750   -2.0097    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -2.3986    1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -1.4945    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -1.1823   -0.8803 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -2.3643   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2560   -2.7066    1.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2626   -2.0560    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -1.2367   -0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8808    2.2947   -2.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543    2.1372   -3.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    1.4313   -3.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    2.9847   -3.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    3.4703   -4.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    2.8912   -5.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7900    4.9682   -3.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744    3.4564   -2.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945    4.9228   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056    2.8551   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330    1.6148   -0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    1.1415    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    1.5058   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742   -0.5791   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -0.1964   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -3.2481    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -2.3590    2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -3.4373    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513   -0.5575    1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -1.9520    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -2.8446   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -3.1110   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446   -2.0752   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9024   -2.8244    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8774   -1.4251    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    2.6942   -4.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977    2.8104   -6.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670    3.5487   -6.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6879    1.8857   -5.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  9  2  0
 17 18  1  0
 14 15  1  0
  8  7  1  0
  9  8  1  0
  7  6  1  0
  8 17  1  0
  6 22  2  0
 17 16  1  0
 22 25  1  0
 16 15  1  0
 25  3  2  0
 11 12  1  0
  3  4  1  0
 11 10  2  0
  4  5  2  0
  5  6  1  0
 10  9  1  0
 22 23  1  0
 23 24  2  0
 14 13  1  0
 23 47  1  0
 13 12  2  0
 25 26  1  0
 12 19  1  0
 26 27  1  0
 19 20  1  0
  3  2  1  0
 20 21  1  0
  2  1  1  0
 21 11  1  0
  8 35  1  6
 10 36  1  0
 13 37  1  0
 16 40  1  0
 16 41  1  0
 15 38  1  0
 15 39  1  0
 20 45  1  0
 20 46  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
  7 33  1  0
  7 34  1  0
  4 31  1  0
  5 32  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃NO₅

Average Mass

369.4170 Da

Monoisotopic Mass

369.15762 Da

IUPAC Name

2,3-dimethoxy-6-{[(5R)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl}benzaldehyde

Traditional Name

2,3-dimethoxy-6-{[(5R)-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl}benzaldehyde

CAS Registry Number

Not Available

SMILES

[H]C(=O)C1=C(C([H])=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])[C@@]1([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C2=C1C([H])=C1OC([H])([H])OC1=C2[H]

InChI Identifier

InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(22)8-13-4-5-18(24-2)21(25-3)16(13)11-23/h4-5,9-11,17H,6-8,12H2,1-3H3/t17-/m1/s1

InChI Key

ROAHDZJDHGLGBA-QGZVFWFLSA-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
Corydalis cava	JEOL database	Meyer, A. M., et al, Phytochem. Letts. 1, 168 (2008)
Hydrastis canadensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
Dimethoxybenzene
O-dimethoxybenzene
Benzodioxole
Anisole
Benzaldehyde
Methoxybenzene
Benzoyl
Phenol ether
Phenoxy compound
Alkyl aryl ether
Aralkylamine
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Acetal
Azacycle
Oxacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Amine
Hydrocarbon derivative
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:68990 )

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	2.74	ALOGPS
logP	3.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	7.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.23 m³·mol⁻¹	ChemAxon
Polarizability	39.94 Å³	ChemAxon
Number of Rings	4	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

8039813

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9864120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chlebek J, Macakova K, Cahlikovi L, Kurfurst M, Kunes J, Opletal L: Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava (Fumariaceae). Nat Prod Commun. 2011 May;6(5):607-10. [PubMed:21615017 ]
Weber HA, Zart MK, Hodges AE, Molloy HM, O'Brien BM, Moody LA, Clark AP, Harris RK, Overstreet JD, Smith CS: Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. J Agric Food Chem. 2003 Dec 3;51(25):7352-8. doi: 10.1021/jf034339r. [PubMed:14640583 ]
Hwang BY, Roberts SK, Chadwick LR, Wu CD, Kinghorn AD: Antimicrobial constituents from goldenseal (the Rhizomes of Hydrastis canadensis) against selected oral pathogens. Planta Med. 2003 Jul;69(7):623-7. doi: 10.1055/s-2003-41115. [PubMed:12898417 ]
Weber HA, Zart MK, Hodges AE, White KD, Barnes SM, Moody LA, Clark AP, Harris RK, Overstreet JD, Smith CS: Method validation for determination of alkaloid content in goldenseal root powder. J AOAC Int. 2003 May-Jun;86(3):476-83. [PubMed:12852562 ]
Scazzocchio F, Cometa MF, Tomassini L, Palmery M: Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids. Planta Med. 2001 Aug;67(6):561-4. doi: 10.1055/s-2001-16493. [PubMed:11509983 ]
Meyer, A. M., et al. (2008). Meyer, A. M., et al, Phytochem. Letts. 1, 168 (2008). Phytochem..

Showing NP-Card for R(-)-canadaline (NP0037942)

MOL for NP0037942 (R(-)-canadaline)

3D MOL for NP0037942 (R(-)-canadaline)

3D SDF for NP0037942 (R(-)-canadaline)

3D-SDF for NP0037942 (R(-)-canadaline)

PDB for NP0037942 (R(-)-canadaline)

3D PDB for NP0037942 (R(-)-canadaline)

SMILES for NP0037942 (R(-)-canadaline)

INCHI for NP0037942 (R(-)-canadaline)

Structure for NP0037942 (R(-)-canadaline)

3D Structure for NP0037942 (R(-)-canadaline)