NP-MRD: Showing NP-Card for melohenine A (NP0038699)

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Record Information

Version

2.0

Created at

2021-06-20 21:19:03 UTC

Updated at

2021-06-30 00:11:37 UTC

NP-MRD ID

NP0038699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

melohenine A

Provided By

JEOL Database JEOL Logo

Description

(1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1¹⁰,¹⁶.0¹,¹⁵.0²,⁷.0⁸,¹⁵.0⁹,¹³.0²⁰,²³]Pentacosa-2,4,6-trien-10-ol belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. melohenine A is found in Melodinus henryi. melohenine A was first documented in 2009 (Feng, T., et al.). Based on a literature review very few articles have been published on (1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1¹⁰,¹⁶.0¹,¹⁵.0²,⁷.0⁸,¹⁵.0⁹,¹³.0²⁰,²³]Pentacosa-2,4,6-trien-10-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123193D          

 60 67  0  0  0  0            999 V2000
    2.6422    4.5480    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202    3.4961   -0.4921 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0118    2.0502    0.0360 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5904    1.0688   -0.9962 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6163   -1.2269   -1.7465 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2085   -1.2462   -2.3395 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.2355   -0.7488    0.0442 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.6456    1.3151   -1.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 30  1  0  0  0  0
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  8 19  1  0  0  0  0
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 16 17  1  0  0  0  0
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M  END

     RDKit          3D

 60 67  0  0  0  0  0  0  0  0999 V2000
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    3.1202    3.4961   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202123193D          

 60 67  0  0  0  0            999 V2000
    2.6422    4.5480    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202    3.4961   -0.4921 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.7117    0.2315    1.0839 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.0832    1.2340   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -2.2342   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0153   -2.1954   -2.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.4575   -3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261   -3.8715   -0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5355   -4.5867   -0.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4018    0.2706    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492   -0.1026    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 30  1  0  0  0  0
 13 14  2  0  0  0  0
  8 19  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 20 28  1  0  0  0  0
 30  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
 28 29  1  0  0  0  0
 19 18  1  6  0  0  0
 29 30  1  0  0  0  0
 16 17  1  0  0  0  0
 20 19  1  0  0  0  0
 20 49  1  6  0  0  0
 22 24  1  0  0  0  0
 18 17  1  0  0  0  0
 10 11  1  0  0  0  0
 28  3  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
  3  4  1  0  0  0  0
 11 12  2  0  0  0  0
  3  2  1  0  0  0  0
 14  9  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
 17 25  1  0  0  0  0
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 20 21  1  0  0  0  0
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 15 16  1  0  0  0  0
 22 23  1  1  0  0  0
 16 22  1  0  0  0  0
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  3 36  1  1  0  0  0
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 26 55  1  0  0  0  0
 27 56  1  0  0  0  0
 23 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@]2(O[H])C([H])([H])[C@@]3([H])[C@@]4([H])C([H])([H])[C@]5([H])N(C([H])([H])C([H])([H])[C@@]55C6=C([H])C([H])=C([H])C([H])=C6N6[C@]2([H])[C@]1([H])O[C@]356)C([H])([H])[C@@]4([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N2O4/c1-2-13-11-25-8-7-22-15-5-3-4-6-17(15)26-21-20-18(12-27)29-23(21,28)10-16(24(22,26)30-20)14(13)9-19(22)25/h3-6,13-14,16,18-21,27-28H,2,7-12H2,1H3/t13-,14+,16+,18-,19+,20-,21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
SUBLYHLPTDOKTD-JXNIYVFESA-N

> <FORMULA>
C24H30N2O4

> <MOLECULAR_WEIGHT>
410.514

> <EXACT_MASS>
410.220557454

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.94703690308294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1^{10,16}.0^{1,15}.0^{2,7}.0^{8,15}.0^{9,13}.0^{20,23}]pentacosa-2,4,6-trien-10-ol

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.066733722043299

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.592375507436433

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.447589694013026

> <JCHEM_PKA_STRONGEST_BASIC>
10.580369643860056

> <JCHEM_POLAR_SURFACE_AREA>
65.4

> <JCHEM_REFRACTIVITY>
110.47779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1^{10,16}.0^{1,15}.0^{2,7}.0^{8,15}.0^{9,13}.0^{20,23}]pentacosa-2,4,6-trien-10-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 67  0  0  0  0  0  0  0  0999 V2000
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  8 30  1  0
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 28  3  1  0
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 14  9  1  0
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 12 13  1  0
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 15 16  1  0
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 11 44  1  0
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 29 58  1  0
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 30 60  1  1
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 17 48  1  6
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 25 53  1  6
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 26 55  1  0
 27 56  1  0
 23 52  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       2.642   4.548   0.498  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.120   3.496  -0.492  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.012   2.050   0.036  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   1.069  -0.996  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.523  -0.342  -0.572  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.616  -1.227  -1.746  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.208  -1.246  -2.340  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.280  -0.978  -1.139  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.337  -2.136  -0.854  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.618  -3.495  -0.771  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.428  -4.375  -0.495  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.729  -3.892  -0.301  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.998  -2.523  -0.380  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.961  -1.651  -0.659  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.023  -0.275  -0.757  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.058   0.447  -1.474  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.512   0.454  -2.885  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.060   0.391  -2.740  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.248   0.183  -1.333  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.551   1.592  -0.712  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.776   2.269  -0.220  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.986   1.965  -1.126  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.198   2.398  -0.522  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.831   2.721  -2.336  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.898   1.808  -3.448  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.308   1.858  -4.046  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.304   1.441  -3.118  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.582   1.614   0.455  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.712   0.232   1.084  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.236  -0.749   0.044  0.00  0.00           C+0
HETATM   31  H   UNK     0       2.866   5.550   0.117  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.562   4.491   0.655  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.142   4.435   1.465  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.173   3.704  -0.724  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.575   3.616  -1.434  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.649   1.999   0.932  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.646   1.315  -1.171  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.083   1.234  -1.955  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.898  -2.234  -1.415  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.373  -0.905  -2.470  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.015  -2.195  -2.850  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.136  -0.458  -3.096  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.626  -3.872  -0.913  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.234  -5.442  -0.424  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.535  -4.587  -0.080  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.005  -2.155  -0.211  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.064   0.035  -1.363  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.820  -0.396  -3.501  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.916   2.231  -1.525  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.011   1.933   0.800  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.619   3.353  -0.153  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.982   3.211  -0.035  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.175   2.152  -4.195  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.555   2.879  -4.355  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.373   1.206  -4.923  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.279   2.074  -2.368  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.243   2.301   1.239  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.402   0.271   1.937  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.749  -0.103   1.489  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.428  -1.696   0.568  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1   34   35                                             
CONECT    3   28    4    2   36                                             
CONECT    4    5    3   37   38                                             
CONECT    5   30    6    4                                                  
CONECT    6    5    7   39   40                                             
CONECT    7    6    8   41   42                                             
CONECT    8   30   19    9    7                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   44                                                  
CONECT   12   11   13   45                                                  
CONECT   13   14   12   46                                                  
CONECT   14   13   15    9                                                  
CONECT   15   14   19   16                                                  
CONECT   16   17   15   22   47                                             
CONECT   17   16   18   25   48                                             
CONECT   18   19   17                                                       
CONECT   19    8   18   20   15                                             
CONECT   20   28   19   49   21                                             
CONECT   21   20   22   50   51                                             
CONECT   22   24   23   16   21                                             
CONECT   23   22   52                                                       
CONECT   24   22   25                                                       
CONECT   25   17   24   26   53                                             
CONECT   26   25   27   54   55                                             
CONECT   27   26   56                                                       
CONECT   28   20   29    3   57                                             
CONECT   29   28   30   58   59                                             
CONECT   30    8    5   29   60                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   23                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  134    0
END

RDKit          3D

60 67  0  0  0  0  0  0  0  0999 V2000
    2.6422    4.5480    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202    3.4961   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118    2.0502    0.0360 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5904    1.0688   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -0.3416   -0.5715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163   -1.2269   -1.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085   -1.2462   -2.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -0.9783   -1.1387 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3368   -2.1364   -0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183   -3.4949   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4282   -4.3749   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -3.8917   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9983   -2.5225   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9608   -1.6514   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0233   -0.2751   -0.7574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579    0.4473   -1.4737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5121    0.4540   -2.8849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0600    0.3910   -2.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    0.1827   -1.3329 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5512    1.5924   -0.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7762    2.2688   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861    1.9651   -1.1264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1980    2.3978   -0.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    2.7210   -2.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984    1.8082   -3.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3079    1.8581   -4.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3041    1.4414   -3.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5820    1.6140    0.4551 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7117    0.2315    1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355   -0.7488    0.0442 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8657    5.5498    0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    4.4907    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    4.4349    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729    3.7039   -0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748    3.6162   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6492    1.9990    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456    1.3151   -1.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832    1.2340   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -2.2342   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3732   -0.9050   -2.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153   -2.1954   -2.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.4575   -3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261   -3.8715   -0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -5.4424   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5355   -4.5867   -0.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048   -2.1549   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0645    0.0346   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -0.3961   -3.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    2.2312   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108    1.9331    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    3.3531   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    3.2107   -0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    2.1523   -4.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554    2.8789   -4.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    1.2062   -4.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789    2.0735   -2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431    2.3015    1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018    0.2706    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492   -0.1026    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -1.6959    0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 30  1  0
 13 14  2  0
  8 19  1  0
  8  9  1  0
  9 10  2  0
 20 28  1  0
 30  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
 28 29  1  0
 19 18  1  6
 29 30  1  0
 16 17  1  0
 20 19  1  0
 20 49  1  6
 22 24  1  0
 18 17  1  0
 10 11  1  0
 28  3  1  0
 14 15  1  0
  5  4  1  0
  3  4  1  0
 11 12  2  0
  3  2  1  0
 14  9  1  0
  2  1  1  0
 12 13  1  0
 17 25  1  0
 24 25  1  0
 20 21  1  0
 25 26  1  0
 19 15  1  0
 26 27  1  0
 15 16  1  0
 22 23  1  1
 16 22  1  0
 28 57  1  1
 22 21  1  0
  3 36  1  1
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 29 58  1  0
 29 59  1  0
 16 47  1  6
 21 50  1  0
 21 51  1  0
 30 60  1  1
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 17 48  1  6
  4 37  1  0
  4 38  1  0
  2 34  1  0
  2 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 53  1  6
 26 54  1  0
 26 55  1  0
 27 56  1  0
 23 52  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀N₂O₄

Average Mass

410.5140 Da

Monoisotopic Mass

410.22056 Da

IUPAC Name

(1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1^{10,16}.0^{1,15}.0^{2,7}.0^{8,15}.0^{9,13}.0^{20,23}]pentacosa-2,4,6-trien-10-ol

Traditional Name

(1R,9R,10R,12R,13S,15R,16S,17S,18S,23S)-18-ethyl-12-(hydroxymethyl)-11,14-dioxa-8,20-diazaoctacyclo[15.5.2.1^{10,16}.0^{1,15}.0^{2,7}.0^{8,15}.0^{9,13}.0^{20,23}]pentacosa-2,4,6-trien-10-ol

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@]2(O[H])C([H])([H])[C@@]3([H])[C@@]4([H])C([H])([H])[C@]5([H])N(C([H])([H])C([H])([H])[C@@]55C6=C([H])C([H])=C([H])C([H])=C6N6[C@]2([H])[C@]1([H])O[C@]356)C([H])([H])[C@@]4([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H30N2O4/c1-2-13-11-25-8-7-22-15-5-3-4-6-17(15)26-21-20-18(12-27)29-23(21,28)10-16(24(22,26)30-20)14(13)9-19(22)25/h3-6,13-14,16,18-21,27-28H,2,7-12H2,1H3/t13-,14+,16+,18-,19+,20-,21-,22-,23-,24-/m1/s1

InChI Key

SUBLYHLPTDOKTD-JXNIYVFESA-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
Melodinus henryi	JEOL database	Feng, T., et al, Org. Lett. 11, 4834 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Dialkylarylamine
Oxepane
Aralkylamine
Piperidine
Monosaccharide
Benzenoid
N-alkylpyrrolidine
Oxazolidine
Oxolane
Pyrrolidine
Hemiacetal
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary alcohol
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	1.89	ALOGPS
logP	2.07	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.45	ChemAxon
pKa (Strongest Basic)	10.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.48 m³·mol⁻¹	ChemAxon
Polarizability	43.95 Å³	ChemAxon
Number of Rings	8	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

44520140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Feng, T., et al. (2009). Feng, T., et al, Org. Lett. 11, 4834 (2009). Org. Lett..

Showing NP-Card for melohenine A (NP0038699)

MOL for NP0038699 (melohenine A)

3D MOL for NP0038699 (melohenine A)

3D SDF for NP0038699 (melohenine A)

3D-SDF for NP0038699 (melohenine A)

PDB for NP0038699 (melohenine A)

3D PDB for NP0038699 (melohenine A)

SMILES for NP0038699 (melohenine A)

INCHI for NP0038699 (melohenine A)

Structure for NP0038699 (melohenine A)

3D Structure for NP0038699 (melohenine A)