NP-MRD: Showing NP-Card for mersifoline B (NP0037324)

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Record Information

Version

2.0

Created at

2021-06-20 20:16:27 UTC

Updated at

2021-06-30 00:09:28 UTC

NP-MRD ID

NP0037324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mersifoline B

Provided By

JEOL Database JEOL Logo

Description

10,14-Dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1²,⁶.0¹,¹¹.0¹⁸,²¹.0⁹,²²]Docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring. mersifoline B is found in Kopsia singapurensis. mersifoline B was first documented in 2008 (Subramaniam, G., et al.). Based on a literature review very few articles have been published on 10,14-dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1²,⁶.0¹,¹¹.0¹⁸,²¹.0⁹,²²]Docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122163D          

 60 65  0  0  0  0            999 V2000
   -3.0600   -3.4083   -4.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -2.7054   -3.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122163D          

 60 65  0  0  0  0            999 V2000
   -3.0600   -3.4083   -4.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -2.7054   -3.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0208   -3.0101   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3945   -2.8801   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
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 34 60  1  6  0  0  0
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 27 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(N2C(=O)OC3=C(OC([H])([H])[H])C([H])=C([H])C(=C23)[C@@]23C([H])([H])C([H])([H])N4C([H])([H])C([H])=C([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]34[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O8/c1-31-14-6-5-13-16-17(14)34-21(29)26(16)24(30,20(28)33-3)15-7-9-22(19(27)32-2)8-4-11-25-12-10-23(13,15)18(22)25/h4-6,8,15,18,30H,7,9-12H2,1-3H3/t15-,18+,22+,23+,24+/m1/s1

> <INCHI_KEY>
MQPRPOARPYYCEN-ZETCXKHESA-N

> <FORMULA>
C24H26N2O8

> <MOLECULAR_WEIGHT>
470.478

> <EXACT_MASS>
470.168915805

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.47903272290098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,14-dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1^{2,6}.0^{1,11}.0^{18,21}.0^{9,22}]docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.4339016590000004

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.341886484873555

> <JCHEM_PKA_STRONGEST_BASIC>
8.302605790804426

> <JCHEM_POLAR_SURFACE_AREA>
114.83999999999999

> <JCHEM_REFRACTIVITY>
117.54429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1^{2,6}.0^{1,11}.0^{18,21}.0^{9,22}]docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 65  0  0  0  0  0  0  0  0999 V2000
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    0.4098    2.6467   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0580   -3.4313   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -4.5470    3.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -5.7392    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -4.5189    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7459   -0.5256    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2633    1.3936    2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0450    1.7063    2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    0.1509    2.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -1.0115    1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4344    4.7695   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2274    6.4718   -1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    6.2669   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1702    0.2509   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 25  2  0
  5  7  1  0
 21  7  1  0
 23 24  2  0
 29 28  1  0
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 24 25  1  0
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  7  8  1  0
 10 11  1  1
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 34 60  1  6
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 28 33  1  0
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  5  6  1  1
 22 23  1  0
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 22 21  1  0
  3  2  1  0
 33 32  1  0
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 32  5  1  0
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 34 18  1  0
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 25 26  1  0
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 21 20  1  1
 24 56  1  0
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  8 40  1  0
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 27 57  1  0
 27 58  1  0
 27 59  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      -3.060  -3.408  -4.486  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.824  -2.705  -3.266  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.981  -1.637  -3.396  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.422  -1.311  -4.437  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.837  -0.889  -2.024  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.652  -1.369  -0.975  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.326  -0.972  -1.606  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.179  -2.402  -1.365  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.687  -2.400  -1.057  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.933  -1.671   0.275  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.301  -2.513   1.433  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.833  -2.090   2.481  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.422  -3.857   1.181  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.920  -4.701   2.219  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.386  -1.569   0.709  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.729  -0.589   1.569  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.737   0.436   2.094  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.571   0.661   1.244  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.250   0.667   1.881  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.718   0.019   0.858  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.051   0.054  -0.478  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.249   1.434  -1.100  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.410   2.647  -0.902  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.123   3.858  -1.422  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   3.890  -2.137  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.946   4.995  -2.646  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.302   6.244  -2.433  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.959   2.680  -2.342  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.167   2.427  -2.983  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.288   1.028  -2.880  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.248   0.391  -3.289  0.00  0.00           O+0
HETATM   32  N   UNK     0      -2.188   0.491  -2.268  0.00  0.00           N+0
HETATM   33  C   UNK     0      -1.394   1.524  -1.865  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.484  -0.180   0.047  0.00  0.00           C+0
HETATM   35  H   UNK     0      -2.129  -3.843  -4.863  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.510  -2.744  -5.231  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.762  -4.221  -4.278  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.560  -1.353  -1.332  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.251  -0.647  -2.491  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.021  -3.010  -2.263  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.395  -2.880  -0.564  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.233  -1.907  -1.872  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.058  -3.431  -1.041  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.486  -4.547   3.143  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.050  -5.739   1.902  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.147  -4.519   2.380  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.107  -2.311   0.382  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.746  -0.526   1.945  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.455   0.144   3.113  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.263   1.394   2.181  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.045   1.706   2.065  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.201   0.151   2.843  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.942  -1.012   1.148  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.673   0.557   0.843  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.325   2.697  -0.317  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.434   4.769  -1.220  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.917   7.021  -2.897  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.227   6.472  -1.365  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.318   6.267  -2.912  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.170   0.251  -0.700  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    7    6    3   32                                             
CONECT    6    5   38                                                       
CONECT    7    5   21    8   39                                             
CONECT    8    7    9   40   41                                             
CONECT    9    8   10   42   43                                             
CONECT   10   11    9   34   15                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   44   45   46                                             
CONECT   15   10   16   47                                                  
CONECT   16   15   17   48                                                  
CONECT   17   16   18   49   50                                             
CONECT   18   19   34   17                                                  
CONECT   19   18   20   51   52                                             
CONECT   20   19   21   53   54                                             
CONECT   21    7   34   22   20                                             
CONECT   22   33   23   21                                                  
CONECT   23   24   22   55                                                  
CONECT   24   23   25   56                                                  
CONECT   25   28   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   57   58   59                                             
CONECT   28   25   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   32   31   29                                                  
CONECT   31   30                                                            
CONECT   32   30   33    5                                                  
CONECT   33   22   28   32                                                  
CONECT   34   21   60   10   18                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   34                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  130    0
END

RDKit          3D

60 65  0  0  0  0  0  0  0  0999 V2000
   -3.0600   -3.4083   -4.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -2.7054   -3.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -1.6366   -3.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224   -1.3105   -4.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -0.8890   -2.0239 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6521   -1.3695   -0.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -0.9724   -1.6059 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1786   -2.4017   -1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870   -2.3998   -1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326   -1.6706    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3011   -2.5133    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332   -2.0900    2.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -3.8568    1.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204   -4.7007    2.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -1.5686    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -0.5886    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369    0.4359    2.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705    0.6605    1.2437 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    0.6670    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    0.0192    0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0510    0.0544   -0.4783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2490    1.4338   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098    2.6467   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228    3.8584   -1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    3.8899   -2.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    4.9946   -2.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    6.2436   -2.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    2.6800   -2.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    2.4270   -2.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2880    1.0283   -2.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484    0.3905   -3.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882    0.4914   -2.2682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942    1.5240   -1.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840   -0.1798    0.0472 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1289   -3.8426   -4.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -2.7445   -5.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619   -4.2206   -4.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598   -1.3528   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.6468   -2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -3.0101   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3945   -2.8801   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333   -1.9069   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0580   -3.4313   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -4.5470    3.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -5.7392    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -4.5189    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -2.3114    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7459   -0.5256    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554    0.1442    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633    1.3936    2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0450    1.7063    2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    0.1509    2.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -1.0115    1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6727    0.5571    0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255    2.6975   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    4.7695   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    7.0208   -2.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    6.4718   -1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    6.2669   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1702    0.2509   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 25  2  0
  5  7  1  0
 21  7  1  0
 23 24  2  0
 29 28  1  0
 22 33  2  0
 18 19  1  0
 24 25  1  0
 19 20  1  0
 21 34  1  0
  7  8  1  0
 10 11  1  1
  8  9  1  0
 34 60  1  6
  9 10  1  0
  7 39  1  6
 34 10  1  0
 32 30  1  0
 28 33  1  0
 30 31  2  0
  5  6  1  1
 22 23  1  0
  5  3  1  0
 22 21  1  0
  3  2  1  0
 33 32  1  0
  3  4  2  0
 32  5  1  0
  2  1  1  0
 34 18  1  0
 11 12  2  0
 10 15  1  0
 11 13  1  0
 15 16  2  0
 13 14  1  0
 29 30  1  0
 16 17  1  0
 25 26  1  0
 17 18  1  0
 26 27  1  0
 21 20  1  1
 24 56  1  0
 23 55  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
  6 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
M  END

View in JSmol

Synonyms

Value	Source
10,14-Dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1,.0,.0,.0,]docosa-2(22),3,5,15-tetraene-10,14-dicarboxylic acid	Generator

Chemical Formula

C₂₄H₂₆N₂O₈

Average Mass

470.4780 Da

Monoisotopic Mass

470.16892 Da

IUPAC Name

10,14-dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1^{2,6}.0^{1,11}.0^{18,21}.0^{9,22}]docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate

Traditional Name

10,14-dimethyl (1R,10S,11R,14R,21R)-10-hydroxy-5-methoxy-8-oxo-7-oxa-9,18-diazahexacyclo[12.6.1.1^{2,6}.0^{1,11}.0^{18,21}.0^{9,22}]docosa-2(22),3,5,15-tetraene-10,14-dicarboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(N2C(=O)OC3=C(OC([H])([H])[H])C([H])=C([H])C(=C23)[C@@]23C([H])([H])C([H])([H])N4C([H])([H])C([H])=C([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]34[H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C24H26N2O8/c1-31-14-6-5-13-16-17(14)34-21(29)26(16)24(30,20(28)33-3)15-7-9-22(19(27)32-2)8-4-11-25-12-10-23(13,15)18(22)25/h4-6,8,15,18,30H,7,9-12H2,1-3H3/t15-,18+,22+,23+,24+/m1/s1

InChI Key

MQPRPOARPYYCEN-ZETCXKHESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Kopsia singapurensis	JEOL database	Subramaniam, G., et al, Tetrahedron 64, 1397 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

Benzoquinoline
Phenanthridine
1,8-phenanthroline
Alpha-amino acid or derivatives
Benzoxazolone
Quinoline
Benzoxazole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
N-alkylpyrrolidine
Methyl ester
Oxazole
Pyrrolidine
Azole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Ether
Alkanolamine
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organonitrogen compound
Amine
Organooxygen 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	1.41	ALOGPS
logP	1.43	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	8.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.54 m³·mol⁻¹	ChemAxon
Polarizability	47.48 Å³	ChemAxon
Number of Rings	6	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

24795659

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Subramaniam, G., et al. (2008). Subramaniam, G., et al, Tetrahedron 64, 1397 (2008). Tetrahedron.

Showing NP-Card for mersifoline B (NP0037324)

MOL for NP0037324 (mersifoline B)

3D MOL for NP0037324 (mersifoline B)

3D SDF for NP0037324 (mersifoline B)

3D-SDF for NP0037324 (mersifoline B)

PDB for NP0037324 (mersifoline B)

3D PDB for NP0037324 (mersifoline B)

SMILES for NP0037324 (mersifoline B)

INCHI for NP0037324 (mersifoline B)

Structure for NP0037324 (mersifoline B)

3D Structure for NP0037324 (mersifoline B)