NP-MRD: Showing NP-Card for maclekarpine C (NP0039304)

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Record Information

Version

2.0

Created at

2021-06-20 21:46:35 UTC

Updated at

2021-06-30 00:12:34 UTC

NP-MRD ID

NP0039304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

maclekarpine C

Provided By

JEOL Database JEOL Logo

Description

Maclekarpine C belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. maclekarpine C is found in Macleaya microcarpa. maclekarpine C was first documented in 2010 (Deng, A.-j.,et al.). Based on a literature review very few articles have been published on Maclekarpine C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123463D          

 51 57  0  0  0  0            999 V2000
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   -2.0024    1.2967   -4.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    1.2172   -3.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    0.0303   -2.8063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4128   -1.0738   -2.2068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2169   -1.4269   -3.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.8317   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363   -1.1931   -3.6349 C   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


  Mrv1652306202123463D          

 51 57  0  0  0  0            999 V2000
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    2.1662    3.6689    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.7020    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487   -2.3750    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -2.5243   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -1.4817    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594    3.2789    4.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515    4.4712    3.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 24 15  2  0  0  0  0
 17 16  2  0  0  0  0
 16 15  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 20  1  0  0  0  0
  4  3  1  0  0  0  0
 24 23  1  0  0  0  0
 18 23  2  0  0  0  0
 24 25  1  0  0  0  0
 15  7  1  0  0  0  0
  3  2  2  0  0  0  0
  2 31  1  0  0  0  0
 31 30  1  0  0  0  0
  4 30  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
 25 26  1  0  0  0  0
  5 25  1  0  0  0  0
  6  7  1  0  0  0  0
 31 32  2  0  0  0  0
  5 38  1  1  0  0  0
 23 22  1  0  0  0  0
  4 37  1  1  0  0  0
 22 21  2  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 18 17  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  0  0  0  0
 22 46  1  0  0  0  0
 19 45  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
  3 36  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C(=O)O[C@@]1([H])[C@]1([H])N(C2=C(C([H])=C([H])C3=C2C([H])=C2OC([H])([H])OC2=C3[H])C2=C([H])C([H])=C3OC([H])([H])OC3=C12)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H19NO6/c1-12-7-20(32-25(12)27)23-21-14(5-6-17-24(21)31-11-28-17)15-4-3-13-8-18-19(30-10-29-18)9-16(13)22(15)26(23)2/h3-9,20,23H,10-11H2,1-2H3/t20-,23+/m1/s1

> <INCHI_KEY>
AYDPSPGOURFSMI-OFNKIYASSA-N

> <FORMULA>
C25H19NO6

> <MOLECULAR_WEIGHT>
429.428

> <EXACT_MASS>
429.121237336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
44.28014424838219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-3-methyl-5-[(23R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2(10),3,8,11,14,16,21-octaen-23-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.595861304666666

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.44225147029271

> <JCHEM_PKA_STRONGEST_BASIC>
0.37619504062253084

> <JCHEM_POLAR_SURFACE_AREA>
66.46000000000001

> <JCHEM_REFRACTIVITY>
115.13730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-3-methyl-5-[(23R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2(10),3,8,11,14,16,21-octaen-23-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 57  0  0  0  0  0  0  0  0999 V2000
   -1.5847    2.2787   -5.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    1.2967   -4.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    1.2172   -3.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    0.0303   -2.8063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4128   -1.0738   -2.2068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2169   -1.4269   -3.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.8317   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363   -1.1931   -3.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926   -2.0909   -4.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -2.6257   -4.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258   -2.3109   -4.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560   -2.9636   -4.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893   -3.6605   -5.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -3.4993   -5.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415    0.1415   -1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    1.0325   -1.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.9543   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    2.0405    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    2.9985    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    3.0850    2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210    2.2691    2.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.3164    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254    1.1647    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    0.2002   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9803   -0.7186   -0.8314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -1.8244    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450    2.5209    3.2119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    3.5908    3.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    3.9561    3.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -0.5183   -3.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8890    0.1675   -5.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -0.1030   -6.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    3.0436   -5.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    2.7837   -6.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.7829   -6.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.9117   -2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513    0.3618   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.9804   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -0.7861   -3.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352   -2.3566   -5.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -3.2851   -6.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -4.7283   -5.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    1.0415   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330    2.6216   -0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662    3.6689    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.7020    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487   -2.3750    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -2.5243   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -1.4817    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594    3.2789    4.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515    4.4712    3.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 24 15  2  0
 17 16  2  0
 16 15  1  0
 21 27  1  0
 27 28  1  0
 28 29  1  0
 29 20  1  0
  4  3  1  0
 24 23  1  0
 18 23  2  0
 24 25  1  0
 15  7  1  0
  3  2  2  0
  2 31  1  0
 31 30  1  0
  4 30  1  0
  5  4  1  0
  6  5  1  0
 25 26  1  0
  5 25  1  0
  6  7  1  0
 31 32  2  0
  5 38  1  1
 23 22  1  0
  4 37  1  1
 22 21  2  0
  2  1  1  0
 11 10  1  0
 18 17  1  0
  6 11  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 16 43  1  0
 17 44  1  0
 22 46  1  0
 19 45  1  0
  8 39  1  0
  9 40  1  0
 28 50  1  0
 28 51  1  0
 26 47  1  0
 26 48  1  0
 26 49  1  0
  3 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 41  1  0
 13 42  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      -1.585   2.279  -5.748  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.002   1.297  -4.727  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.706   1.217  -3.431  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.346   0.030  -2.806  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.413  -1.074  -2.207  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.217  -1.427  -3.066  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.041  -0.832  -2.811  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.136  -1.193  -3.635  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.993  -2.091  -4.700  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.747  -2.626  -4.925  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.326  -2.311  -4.128  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.456  -2.964  -4.514  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.989  -3.660  -5.686  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.426  -3.499  -5.915  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.141   0.142  -1.695  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.217   1.032  -1.564  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.275   1.954  -0.517  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.246   2.041   0.424  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.319   2.999   1.451  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.274   3.085   2.344  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.821   2.269   2.247  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.926   1.316   1.257  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.125   1.165   0.321  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.094   0.200  -0.733  0.00  0.00           C+0
HETATM   25  N   UNK     0      -0.980  -0.719  -0.831  0.00  0.00           N+0
HETATM   26  C   UNK     0      -0.902  -1.824   0.126  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.745   2.521   3.212  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.099   3.591   3.932  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.185   3.956   3.384  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.137  -0.518  -3.877  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.889   0.168  -5.026  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.344  -0.103  -6.123  0.00  0.00           O+0
HETATM   33  H   UNK     0      -0.929   3.044  -5.320  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.456   2.784  -6.176  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.040   1.783  -6.557  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.079   1.912  -2.892  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.051   0.362  -2.034  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.030  -1.980  -2.126  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.128  -0.786  -3.455  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.835  -2.357  -5.329  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.534  -3.285  -6.561  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.205  -4.728  -5.568  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.031   1.042  -2.283  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.133   2.622  -0.458  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.166   3.669   1.548  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.819   0.702   1.202  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.849  -2.375   0.141  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.105  -2.524  -0.150  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.716  -1.482   1.149  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.959   3.279   4.973  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.752   4.471   3.913  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3   31    1                                                  
CONECT    3    4    2   36                                                  
CONECT    4    3   30    5   37                                             
CONECT    5    4    6   25   38                                             
CONECT    6    5    7   11                                                  
CONECT    7   15    6    8                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8   10   40                                                  
CONECT   10   11    9   14                                                  
CONECT   11   10    6   12                                                  
CONECT   12   13   11                                                       
CONECT   13   14   12   41   42                                             
CONECT   14   10   13                                                       
CONECT   15   24   16    7                                                  
CONECT   16   17   15   43                                                  
CONECT   17   16   18   44                                                  
CONECT   18   19   23   17                                                  
CONECT   19   20   18   45                                                  
CONECT   20   21   19   29                                                  
CONECT   21   20   27   22                                                  
CONECT   22   23   21   46                                                  
CONECT   23   24   18   22                                                  
CONECT   24   15   23   25                                                  
CONECT   25   24   26    5                                                  
CONECT   26   25   47   48   49                                             
CONECT   27   21   28                                                       
CONECT   28   27   29   50   51                                             
CONECT   29   28   20                                                       
CONECT   30   31    4                                                       
CONECT   31    2   30   32                                                  
CONECT   32   31                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   22                                                            
CONECT   47   26                                                            
CONECT   48   26                                                            
CONECT   49   26                                                            
CONECT   50   28                                                            
CONECT   51   28                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

RDKit          3D

51 57  0  0  0  0  0  0  0  0999 V2000
   -1.5847    2.2787   -5.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    1.2967   -4.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    1.2172   -3.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    0.0303   -2.8063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4128   -1.0738   -2.2068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2169   -1.4269   -3.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.8317   -2.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363   -1.1931   -3.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926   -2.0909   -4.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -2.6257   -4.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258   -2.3109   -4.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560   -2.9636   -4.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893   -3.6605   -5.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -3.4993   -5.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415    0.1415   -1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    1.0325   -1.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.9543   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    2.0405    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185    2.9985    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    3.0850    2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210    2.2691    2.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.3164    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254    1.1647    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    0.2002   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9803   -0.7186   -0.8314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -1.8244    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450    2.5209    3.2119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    3.5908    3.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    3.9561    3.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -0.5183   -3.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8890    0.1675   -5.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -0.1030   -6.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    3.0436   -5.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    2.7837   -6.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.7829   -6.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.9117   -2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513    0.3618   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.9804   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -0.7861   -3.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352   -2.3566   -5.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -3.2851   -6.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -4.7283   -5.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    1.0415   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330    2.6216   -0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662    3.6689    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.7020    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487   -2.3750    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -2.5243   -0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -1.4817    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594    3.2789    4.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515    4.4712    3.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 24 15  2  0
 17 16  2  0
 16 15  1  0
 21 27  1  0
 27 28  1  0
 28 29  1  0
 29 20  1  0
  4  3  1  0
 24 23  1  0
 18 23  2  0
 24 25  1  0
 15  7  1  0
  3  2  2  0
  2 31  1  0
 31 30  1  0
  4 30  1  0
  5  4  1  0
  6  5  1  0
 25 26  1  0
  5 25  1  0
  6  7  1  0
 31 32  2  0
  5 38  1  1
 23 22  1  0
  4 37  1  1
 22 21  2  0
  2  1  1  0
 11 10  1  0
 18 17  1  0
  6 11  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 16 43  1  0
 17 44  1  0
 22 46  1  0
 19 45  1  0
  8 39  1  0
  9 40  1  0
 28 50  1  0
 28 51  1  0
 26 47  1  0
 26 48  1  0
 26 49  1  0
  3 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 41  1  0
 13 42  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₅H₁₉NO₆

Average Mass

429.4280 Da

Monoisotopic Mass

429.12124 Da

IUPAC Name

(5R)-3-methyl-5-[(23R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2(10),3,8,11,14,16,21-octaen-23-yl]-2,5-dihydrofuran-2-one

Traditional Name

(5R)-3-methyl-5-[(23R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2(10),3,8,11,14,16,21-octaen-23-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(C(=O)O[C@@]1([H])[C@]1([H])N(C2=C(C([H])=C([H])C3=C2C([H])=C2OC([H])([H])OC2=C3[H])C2=C([H])C([H])=C3OC([H])([H])OC3=C12)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H19NO6/c1-12-7-20(32-25(12)27)23-21-14(5-6-17-24(21)31-11-28-17)15-4-3-13-8-18-19(30-10-29-18)9-16(13)22(15)26(23)2/h3-9,20,23H,10-11H2,1-2H3/t20-,23+/m1/s1

InChI Key

AYDPSPGOURFSMI-OFNKIYASSA-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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Macleaya microcarpa	JEOL database	Deng, A.-j.,et al, Phytochemistry 71, 816 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Dihydrobenzophenanthridine alkaloids

Direct Parent

Dihydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Dihydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Naphthalene
Quinoline
Benzodioxole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
2-furanone
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Lactone
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
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	3.78	ALOGPS
logP	4.6	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.44	ChemAxon
pKa (Strongest Basic)	0.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	115.14 m³·mol⁻¹	ChemAxon
Polarizability	44.28 Å³	ChemAxon
Number of Rings	7	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

46223683

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Deng, A.-j.,et al. (2010). Deng, A.-j.,et al, Phytochemistry 71, 816 (2010). Phytochem..

Showing NP-Card for maclekarpine C (NP0039304)

MOL for NP0039304 (maclekarpine C)

3D MOL for NP0039304 (maclekarpine C)

3D SDF for NP0039304 (maclekarpine C)

3D-SDF for NP0039304 (maclekarpine C)

PDB for NP0039304 (maclekarpine C)

3D PDB for NP0039304 (maclekarpine C)

SMILES for NP0039304 (maclekarpine C)

INCHI for NP0039304 (maclekarpine C)

Structure for NP0039304 (maclekarpine C)

3D Structure for NP0039304 (maclekarpine C)