NP-MRD: Showing NP-Card for Chelirubine (NP0023964)

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Record Information

Version

2.0

Created at

2021-04-21 17:21:26 UTC

Updated at

2021-07-26 15:24:09 UTC

NP-MRD ID

NP0023964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chelirubine

Provided By

JEOL Database JEOL Logo

Description

Chelirubine 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. Chelirubine can be extracted and purified from the dried roots of Sanguinaria canadensis (also known as bloodroot plant) as well as from the California poppy (Eschscholzia californica Cham.)(PMID: 8229008 ; PMID: 1822177 ). Chelirubine has also been reported to be found in five other plant species belonging to the family Papaveraceae (Dicranostigma lactucoides, Chelidonium majus, Macleaya cordata, Macleaya microcarpa (Maxim) and Stylophorum lasiocarpum) (PMID:17367981 ). As with other dihydrobenzophenanthridine alkaloids, chelirubine exhibits strong binding to DNA (PMID: 19183968 ). Recently, chelirubine has been found to be useful as a DNA fluorescent probe showing blue (free form) and red (intercalated to DNA) luminescence emission after irradiation by near-UV light (PMID: 23598024 ).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306102103383D          

 45 50  0  0  0  0            999 V2000
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    0.3255   -2.9148   -2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744   -2.0831   -3.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0963   -1.7983   -5.1341 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


  Mrv1652306102103383D          

 45 50  0  0  0  0            999 V2000
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 13 35  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 24 42  1  0  0  0  0
 24 43  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 22 41  1  0  0  0  0
 27 44  1  0  0  0  0
 27 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])N(C2=C3C([H])=C4OC([H])([H])OC4=C([H])C3=C([H])C([H])=C2C2=C(OC([H])([H])[H])C([H])=C3OC([H])([H])OC3=C12)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H17NO6/c1-22-19-11(4-3-10-5-13-14(6-12(10)19)26-8-25-13)17-15(24-2)7-16-20(28-9-27-16)18(17)21(22)23/h3-7,21,23H,8-9H2,1-2H3/t21-/m1/s1

> <INCHI_KEY>
VQHQADFZPDHVME-UHFFFAOYSA-N

> <FORMULA>
C21H17NO6

> <MOLECULAR_WEIGHT>
379.368

> <EXACT_MASS>
379.105587271

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
39.31515824310915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(23R)-15-methoxy-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-1,3,8,10,12,14,16,21-octaen-23-ol

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
3.1937908226666663

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.508961135533884

> <JCHEM_PKA_STRONGEST_BASIC>
-3.888380399317481

> <JCHEM_POLAR_SURFACE_AREA>
69.62000000000002

> <JCHEM_REFRACTIVITY>
99.65450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Chelirubine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 50  0  0  0  0  0  0  0  0999 V2000
    1.6201   -2.7580   -3.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255   -2.9148   -2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744   -2.0831   -3.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245   -2.6134   -4.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -1.7983   -5.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3280   -0.5042   -4.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    0.0400   -3.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -0.7711   -2.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557   -0.1592   -1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480   -0.9133   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016   -0.3064    0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380    1.0835    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834    1.6650    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    3.0360    1.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    3.8317    0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2845    3.2986   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    1.8954   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    1.2613   -1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953    2.0454   -2.5543 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2075    2.6454   -3.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    1.4616   -3.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    1.5255   -2.3029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    5.1537    1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5341    5.0955    2.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425    3.7520    3.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922    0.1353   -5.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -0.9245   -6.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7923   -2.1401   -6.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -3.1111   -4.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -1.7185   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215   -3.3731   -2.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378   -3.6288   -4.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -1.9989   -0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848   -0.9440    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    1.0609    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    3.9630   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672    3.3677   -4.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    1.8832   -4.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    3.1870   -2.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    2.0741   -4.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6758    2.1095   -1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725    5.5559    3.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656    5.6712    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106   -0.5840   -7.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5988   -1.1366   -6.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 21  1  0
 10  9  2  0
 18 17  2  0
  4  5  2  0
 12 11  2  0
 11 10  1  0
 21 19  1  0
 14 25  1  0
  8  3  2  0
 23 15  1  0
 19 18  1  0
 12 13  1  0
 13 14  2  0
 18  9  1  0
 19 20  1  0
  6  7  2  0
 25 24  1  0
  7  8  1  0
  3  2  1  0
 12 17  1  0
  2  1  1  0
 24 23  1  0
 21 22  1  0
  6  5  1  0
 17 16  1  0
  9  8  1  0
 16 15  2  0
  3  4  1  0
 15 14  1  0
  5 28  1  0
 28 27  1  0
 27 26  1  0
 26  6  1  0
  4 32  1  0
 21 40  1  0
 16 36  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 24 42  1  0
 24 43  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 22 41  1  0
 27 44  1  0
 27 45  1  0
M  END

HEADER    PROTEIN                                 10-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUN-21         0                                  
HETATM    1  C   UNK     0       1.620  -2.758  -3.294  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.326  -2.915  -2.709  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.574  -2.083  -3.331  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.224  -2.613  -4.455  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.096  -1.798  -5.134  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.328  -0.504  -4.740  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.714   0.040  -3.622  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.840  -0.771  -2.853  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.256  -0.159  -1.626  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.248  -0.913  -0.558  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.802  -0.306   0.572  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.838   1.083   0.698  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.383   1.665   1.857  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.365   3.036   1.975  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.826   3.832   1.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.285   3.299  -0.151  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.296   1.895  -0.341  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.241   1.261  -1.505  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.795   2.045  -2.554  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.208   2.645  -3.434  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.959   1.462  -3.213  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.037   1.526  -2.303  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.891   5.154   1.311  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.534   5.096   2.601  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.843   3.752   3.027  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.192   0.135  -5.576  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.526  -0.925  -6.495  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.792  -2.140  -6.251  0.00  0.00           O+0
HETATM   29  H   UNK     0       1.627  -3.111  -4.331  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.963  -1.718  -3.245  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.321  -3.373  -2.723  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.038  -3.629  -4.784  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.203  -1.999  -0.569  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.185  -0.944   1.367  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.802   1.061   2.655  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.151   3.963  -0.889  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.267   3.368  -4.107  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.702   1.883  -4.047  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.980   3.187  -2.878  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.231   2.074  -4.081  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.676   2.110  -1.615  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.873   5.556   3.344  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.466   5.671   2.555  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.311  -0.584  -7.514  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.599  -1.137  -6.414  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    8    2    4                                                  
CONECT    4    5    3   32                                                  
CONECT    5    4    6   28                                                  
CONECT    6    7    5   26                                                  
CONECT    7   21    6    8                                                  
CONECT    8    3    7    9                                                  
CONECT    9   10   18    8                                                  
CONECT   10    9   11   33                                                  
CONECT   11   12   10   34                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   35                                                  
CONECT   14   25   13   15                                                  
CONECT   15   23   16   14                                                  
CONECT   16   17   15   36                                                  
CONECT   17   18   12   16                                                  
CONECT   18   17   19    9                                                  
CONECT   19   21   18   20                                                  
CONECT   20   19   37   38   39                                             
CONECT   21    7   19   22   40                                             
CONECT   22   21   41                                                       
CONECT   23   15   24                                                       
CONECT   24   25   23   42   43                                             
CONECT   25   14   24                                                       
CONECT   26   27    6                                                       
CONECT   27   28   26   44   45                                             
CONECT   28    5   27                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   16                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   24                                                            
CONECT   43   24                                                            
CONECT   44   27                                                            
CONECT   45   27                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

RDKit          3D

45 50  0  0  0  0  0  0  0  0999 V2000
    1.6201   -2.7580   -3.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255   -2.9148   -2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744   -2.0831   -3.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245   -2.6134   -4.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -1.7983   -5.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3280   -0.5042   -4.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    0.0400   -3.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -0.7711   -2.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557   -0.1592   -1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480   -0.9133   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016   -0.3064    0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8380    1.0835    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834    1.6650    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    3.0360    1.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    3.8317    0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2845    3.2986   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    1.8954   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    1.2613   -1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953    2.0454   -2.5543 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2075    2.6454   -3.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    1.4616   -3.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    1.5255   -2.3029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    5.1537    1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5341    5.0955    2.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425    3.7520    3.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922    0.1353   -5.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -0.9245   -6.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7923   -2.1401   -6.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -3.1111   -4.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -1.7185   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215   -3.3731   -2.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0378   -3.6288   -4.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -1.9989   -0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848   -0.9440    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    1.0609    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    3.9630   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672    3.3677   -4.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    1.8832   -4.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798    3.1870   -2.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    2.0741   -4.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6758    2.1095   -1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725    5.5559    3.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656    5.6712    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106   -0.5840   -7.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5988   -1.1366   -6.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 21  1  0
 10  9  2  0
 18 17  2  0
  4  5  2  0
 12 11  2  0
 11 10  1  0
 21 19  1  0
 14 25  1  0
  8  3  2  0
 23 15  1  0
 19 18  1  0
 12 13  1  0
 13 14  2  0
 18  9  1  0
 19 20  1  0
  6  7  2  0
 25 24  1  0
  7  8  1  0
  3  2  1  0
 12 17  1  0
  2  1  1  0
 24 23  1  0
 21 22  1  0
  6  5  1  0
 17 16  1  0
  9  8  1  0
 16 15  2  0
  3  4  1  0
 15 14  1  0
  5 28  1  0
 28 27  1  0
 27 26  1  0
 26  6  1  0
  4 32  1  0
 21 40  1  0
 16 36  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 24 42  1  0
 24 43  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 22 41  1  0
 27 44  1  0
 27 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 5-methoxy-13-methyl-	NP-MRD
5-methoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium	NP-MRD
5-Methoxy-13-methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium	NP-MRD

Chemical Formula

C₂₁H₁₇NO₆

Average Mass

379.3680 Da

Monoisotopic Mass

379.10559 Da

IUPAC Name

(23R)-15-methoxy-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-1,3,8,10,12,14,16,21-octaen-23-ol

Traditional Name

Chelirubine

CAS Registry Number

18203-11-7

SMILES

COC1=C2C(C(O)N(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C2OCOC2=C1

InChI Identifier

InChI=1S/C21H17NO6/c1-22-19-11(4-3-10-5-13-14(6-12(10)19)26-8-25-13)17-15(24-2)7-16-20(28-9-27-16)18(17)21(22)23/h3-7,21,23H,8-9H2,1-2H3

InChI Key

VQHQADFZPDHVME-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Bocconia cordata	Plant	KNApSAcK
Chelidonium majus	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Dicranostigma franchetianum Fedde	Plant	KNApSAcK
Dicranostigma lactucoides	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Dicranostigma lactucoides Hook.et Thoms.	Plant	KNApSAcK
Dicranostigma leptopodum Fedde	Plant	KNApSAcK
Eschscholzia californica	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Glaucium squamigerum Kar.et KIR.	Plant	KNApSAcK
Macleaya cordata	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Macleaya microcarpa	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Papaver oreophillum	Plant	KNApSAcK
Sanguinaria canadensis	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)
Stylophorum lasiocarpum	JEOL database	Seckarova, P., et al, Magn. Reson. Chem. 40, 147 (2002)

Chemical Taxonomy

Classification

Not classified

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	2.54	ALOGPS
logP	3.19	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.51	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.65 m³·mol⁻¹	ChemAxon
Polarizability	39.32 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

10228986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15932478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bambagiotti-Alberti M, Pinzauti S, Moneti G, Gratteri P, Coran SA, Vincieri FF: Characterization of Sanguinaria canadensis L. fluid extract by FAB mass spectrometry. J Pharm Biomed Anal. 1991;9(10-12):1083-7. doi: 10.1016/0731-7085(91)80048-e. [PubMed:1822177 ]
Suchomelova J, Bochorakova H, Paulova H, Musil P, Taborska E: HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae. J Pharm Biomed Anal. 2007 May 9;44(1):283-7. doi: 10.1016/j.jpba.2007.02.005. Epub 2007 Feb 13. [PubMed:17367981 ]
Urbanova J, Lubal P, Slaninova I, Taborska E, Taborsky P: Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA. Anal Bioanal Chem. 2009 Jun;394(4):997-1002. doi: 10.1007/s00216-009-2601-7. Epub 2009 Jan 30. [PubMed:19183968 ]
Cline SD, McHale RJ, Coscia CJ: Differential enhancement of benzophenanthridine alkaloid content in cell suspension cultures of Sanguinaria canadensis under conditions of combined hormonal deprivation and fungal elicitation. J Nat Prod. 1993 Aug;56(8):1219-28. doi: 10.1021/np50098a003. [PubMed:8229008 ]
Rajecky M, Slaninova I, Mokrisova P, Urbanova J, Palkovsky M, Taborska E, Taborsky P: Alkaloid chelirubine and DNA: blue and red luminescence. Talanta. 2013 Feb 15;105:317-9. doi: 10.1016/j.talanta.2012.10.045. Epub 2012 Nov 2. [PubMed:23598024 ]
Pavlína Sečkářová, Radek Marek, Jiří Dostál, Roger Dommisse, Eddy L. Esmans (2002). Pavlína Sečkářová, Radek Marek, Jiří Dostál, Roger Dommisse, Eddy L. Esmans. Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy. Magn. Reson. Chem. 40(2), 147-152. Magnetic Resonance in Chemistry.
JEOL [Link]

Showing NP-Card for Chelirubine (NP0023964)

MOL for NP0023964 (Chelirubine)

3D MOL for NP0023964 (Chelirubine)

3D SDF for NP0023964 (Chelirubine)

3D-SDF for NP0023964 (Chelirubine)

PDB for NP0023964 (Chelirubine)

3D PDB for NP0023964 (Chelirubine)

SMILES for NP0023964 (Chelirubine)

INCHI for NP0023964 (Chelirubine)

Structure for NP0023964 (Chelirubine)

3D Structure for NP0023964 (Chelirubine)