NP-MRD: Showing NP-Card for melicodenine H (NP0041203)

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Record Information

Version

2.0

Created at

2021-06-20 23:10:16 UTC

Updated at

2021-06-30 00:15:34 UTC

NP-MRD ID

NP0041203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

melicodenine H

Provided By

JEOL Database JEOL Logo

Description

(9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-5,6,9,10-tetrahydrophenanthridin-6-one belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. melicodenine H is found in Melicope denhamii. melicodenine H was first documented in 2012 (Nakashima, K., et al.). Based on a literature review very few articles have been published on (9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-5,6,9,10-tetrahydrophenanthridin-6-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101103D          

 53 57  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101103D          

 53 57  0  0  0  0            999 V2000
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    0.3408   -1.9123    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -4.1634    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679   -5.2903    2.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -4.1440    3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -3.1952    3.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -1.6511    4.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855   -2.5216    5.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -0.3367   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    1.5950    2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7251    1.2362   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244   -0.0761   -3.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.3546   -2.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379   -0.3067   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    3.8118    3.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267    2.2023    3.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 19  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  4  1  0  0  0  0
  4 19  1  0  0  0  0
  4  3  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  2  0  0  0  0
 17  7  1  0  0  0  0
 22 21  2  0  0  0  0
  9 10  2  0  0  0  0
 21 20  1  0  0  0  0
 20 25  2  0  0  0  0
 22 23  1  0  0  0  0
 15 16  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  2  0  0  0  0
  8  7  2  0  0  0  0
  9 14  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 22  1  0  0  0  0
  3  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 14  2  0  0  0  0
 25 26  1  0  0  0  0
 11 12  2  0  0  0  0
  9  8  1  0  0  0  0
 26 27  1  0  0  0  0
 19 20  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  0  0  0  0
 10 39  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
  6 38  1  0  0  0  0
  5 37  1  0  0  0  0
  4 36  1  6  0  0  0
 19 46  1  6  0  0  0
 24 48  1  0  0  0  0
 21 47  1  0  0  0  0
 29 52  1  0  0  0  0
 29 53  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C2C(=C1[H])N(C(=O)C1=C2[C@]([H])(C2=C(OC([H])([H])[H])C([H])=C3OC([H])([H])OC3=C2[H])[C@]([H])(C([H])=C1[H])C([H])([H])OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H23NO5/c1-25-18-7-5-4-6-15(18)23-16(24(25)26)9-8-14(12-27-2)22(23)17-10-20-21(30-13-29-20)11-19(17)28-3/h4-11,14,22H,12-13H2,1-3H3/t14-,22+/m1/s1

> <INCHI_KEY>
AUWKBILYNITFJV-PEBXRYMYSA-N

> <FORMULA>
C24H23NO5

> <MOLECULAR_WEIGHT>
405.45

> <EXACT_MASS>
405.157622845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.79743213734322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-5,6,9,10-tetrahydrophenanthridin-6-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.677449259666668

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.26615173605958165

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
113.57579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-9,10-dihydrophenanthridin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.5827    1.8180   -3.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646    2.2297   -2.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894    1.1073   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    1.6032   -0.6850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6643    2.2852    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1605    1.6869    1.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.3298    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -0.2863    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -1.6636    1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -2.3589    0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -3.6537    1.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -4.2827    2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7999   -3.6139    2.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431   -2.3067    2.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -1.6273    3.1374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2837    4.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6043   -0.3384    2.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492    0.2652    3.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.4218    0.0241 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4527    0.9093    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.4858    1.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    1.9245    2.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    1.8237    1.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8366    1.2857    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5817    0.8310   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427    0.2894   -1.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047    0.3272   -2.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736    2.3131    1.8941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    2.7373    3.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664    2.4926    3.3586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399    1.2291   -4.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9120    2.7114   -4.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649    1.2366   -3.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2309    0.4515   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    0.5477   -2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    2.3700   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    3.2855   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858    2.2093    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -1.9123    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -4.1634    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679   -5.2903    2.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -4.1440    3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -3.1952    3.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -1.6511    4.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855   -2.5216    5.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -0.3367   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    1.5950    2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7251    1.2362   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244   -0.0761   -3.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.3546   -2.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379   -0.3067   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    3.8118    3.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267    2.2023    3.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 19  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4 19  1  0
  4  3  1  0
 14 15  1  0
 15 17  1  0
 25 24  1  0
 24 23  2  0
 17  7  1  0
 22 21  2  0
  9 10  2  0
 21 20  1  0
 20 25  2  0
 22 23  1  0
 15 16  1  0
 10 11  1  0
 17 18  2  0
  8  7  2  0
  9 14  1  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 22  1  0
  3  2  1  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
 25 26  1  0
 11 12  2  0
  9  8  1  0
 26 27  1  0
 19 20  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 10 39  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
  6 38  1  0
  5 37  1  0
  4 36  1  6
 19 46  1  6
 24 48  1  0
 21 47  1  0
 29 52  1  0
 29 53  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.583   1.818  -3.865  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.865   2.230  -2.710  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.389   1.107  -1.957  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.671   1.603  -0.685  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.664   2.285   0.225  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.160   1.687   1.315  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.795   0.330   1.695  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.740  -0.286   1.121  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.381  -1.664   1.546  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.291  -2.359   0.987  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.038  -3.654   1.392  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.718  -4.283   2.367  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.800  -3.614   2.938  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.143  -2.307   2.542  0.00  0.00           C+0
HETATM   15  N   UNK     0      -3.246  -1.627   3.137  0.00  0.00           N+0
HETATM   16  C   UNK     0      -4.031  -2.284   4.173  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.604  -0.338   2.770  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.549   0.265   3.283  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.927   0.422   0.024  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.453   0.909   0.506  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.604   1.486   1.784  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.853   1.925   2.164  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.936   1.824   1.330  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.837   1.286   0.064  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.582   0.831  -0.362  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.343   0.289  -1.601  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.405   0.327  -2.547  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.074   2.313   1.894  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.576   2.737   3.181  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.166   2.493   3.359  0.00  0.00           O+0
HETATM   31  H   UNK     0      -2.940   1.229  -4.526  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.912   2.711  -4.402  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.465   1.237  -3.580  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.231   0.452  -1.700  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.690   0.548  -2.589  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.947   2.370  -0.996  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.992   3.285  -0.047  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.886   2.209   1.935  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.341  -1.912   0.225  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.887  -4.163   0.944  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.468  -5.290   2.688  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.361  -4.144   3.701  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.481  -3.195   3.766  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.844  -1.651   4.541  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.385  -2.522   5.024  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.759  -0.337  -0.751  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.230   1.595   2.470  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.725   1.236  -0.551  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.024  -0.076  -3.490  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.735   1.355  -2.733  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.238  -0.307  -2.226  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.763   3.812   3.292  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.127   2.202   3.963  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   34   35                                             
CONECT    4    5   19    3   36                                             
CONECT    5    6    4   37                                                  
CONECT    6    7    5   38                                                  
CONECT    7    6   17    8                                                  
CONECT    8   19    7    9                                                  
CONECT    9   10   14    8                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12   40                                                  
CONECT   12   13   11   41                                                  
CONECT   13   12   14   42                                                  
CONECT   14   15    9   13                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   43   44   45                                             
CONECT   17   15    7   18                                                  
CONECT   18   17                                                            
CONECT   19    8    4   20   46                                             
CONECT   20   21   25   19                                                  
CONECT   21   22   20   47                                                  
CONECT   22   21   23   30                                                  
CONECT   23   24   22   28                                                  
CONECT   24   25   23   48                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   49   50   51                                             
CONECT   28   23   29                                                       
CONECT   29   28   30   52   53                                             
CONECT   30   29   22                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   19                                                            
CONECT   47   21                                                            
CONECT   48   24                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
CONECT   51   27                                                            
CONECT   52   29                                                            
CONECT   53   29                                                            
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
   -3.5827    1.8180   -3.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646    2.2297   -2.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894    1.1073   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    1.6032   -0.6850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6643    2.2852    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1605    1.6869    1.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.3298    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -0.2863    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -1.6636    1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -2.3589    0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -3.6537    1.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -4.2827    2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7999   -3.6139    2.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431   -2.3067    2.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -1.6273    3.1374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2837    4.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6043   -0.3384    2.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492    0.2652    3.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.4218    0.0241 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4527    0.9093    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.4858    1.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    1.9245    2.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    1.8237    1.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8366    1.2857    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5817    0.8310   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427    0.2894   -1.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047    0.3272   -2.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736    2.3131    1.8941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    2.7373    3.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664    2.4926    3.3586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399    1.2291   -4.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9120    2.7114   -4.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649    1.2366   -3.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2309    0.4515   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    0.5477   -2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    2.3700   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    3.2855   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858    2.2093    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -1.9123    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -4.1634    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679   -5.2903    2.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3613   -4.1440    3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -3.1952    3.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -1.6511    4.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855   -2.5216    5.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -0.3367   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    1.5950    2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7251    1.2362   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244   -0.0761   -3.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.3546   -2.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379   -0.3067   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    3.8118    3.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267    2.2023    3.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 19  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4 19  1  0
  4  3  1  0
 14 15  1  0
 15 17  1  0
 25 24  1  0
 24 23  2  0
 17  7  1  0
 22 21  2  0
  9 10  2  0
 21 20  1  0
 20 25  2  0
 22 23  1  0
 15 16  1  0
 10 11  1  0
 17 18  2  0
  8  7  2  0
  9 14  1  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 22  1  0
  3  2  1  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
 25 26  1  0
 11 12  2  0
  9  8  1  0
 26 27  1  0
 19 20  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 10 39  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
  6 38  1  0
  5 37  1  0
  4 36  1  6
 19 46  1  6
 24 48  1  0
 21 47  1  0
 29 52  1  0
 29 53  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃NO₅

Average Mass

405.4500 Da

Monoisotopic Mass

405.15762 Da

IUPAC Name

(9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-5,6,9,10-tetrahydrophenanthridin-6-one

Traditional Name

(9S,10R)-10-(6-methoxy-2H-1,3-benzodioxol-5-yl)-9-(methoxymethyl)-5-methyl-9,10-dihydrophenanthridin-6-one

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C([H])=C2C(=C1[H])N(C(=O)C1=C2[C@]([H])(C2=C(OC([H])([H])[H])C([H])=C3OC([H])([H])OC3=C2[H])[C@]([H])(C([H])=C1[H])C([H])([H])OC([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H23NO5/c1-25-18-7-5-4-6-15(18)23-16(24(25)26)9-8-14(12-27-2)22(23)17-10-20-21(30-13-29-20)11-19(17)28-3/h4-11,14,22H,12-13H2,1-3H3/t14-,22+/m1/s1

InChI Key

AUWKBILYNITFJV-PEBXRYMYSA-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
Melicope denhamii	JEOL database	Nakashima, K., et al, Tetrahedron 68, 2421 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Dihydroquinolone
Isoquinolone
Dihydroquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Pyridinone
Benzenoid
Pyridine
Heteroaromatic compound
Lactam
Acetal
Dialkyl ether
Ether
Oxacycle
Azacycle
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
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	2.4	ALOGPS
logP	2.68	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.58 m³·mol⁻¹	ChemAxon
Polarizability	43.8 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57341019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nakashima, K., et al. (2012). Nakashima, K., et al, Tetrahedron 68, 2421 (2012). Tetrahedron.

Showing NP-Card for melicodenine H (NP0041203)

MOL for NP0041203 (melicodenine H)

3D MOL for NP0041203 (melicodenine H)

3D SDF for NP0041203 (melicodenine H)

3D-SDF for NP0041203 (melicodenine H)

PDB for NP0041203 (melicodenine H)

3D PDB for NP0041203 (melicodenine H)

SMILES for NP0041203 (melicodenine H)

INCHI for NP0041203 (melicodenine H)

Structure for NP0041203 (melicodenine H)

3D Structure for NP0041203 (melicodenine H)