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Showing NP-Card for Pantherinine (NP0070282)

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Record Information
Version2.0
Created at2022-04-28 15:35:30 UTC
Updated at2022-04-28 15:35:30 UTC
NP-MRD IDNP0070282
Secondary Accession NumbersNone
Natural Product Identification
Common NamePantherinine
DescriptionPantherinine belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridones. Pyrido[2,3,4-kl]acridones are compounds containing a pyrido[2,3,4-kl]acridine carrying a C=O group. Pantherinine is found in Aplidium pantherinum. Pantherinine was first documented in 1993 (PMID: 8277319). Based on a literature review very few articles have been published on Pantherinine.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0070282 (Pantherinine)


  Mrv1652304282217352D          

 20 23  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  2  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
Download

3D MOL for NP0070282 (Pantherinine)

     RDKit          3D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -4.6499   -1.2236    0.1896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428   -0.6688    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761   -1.4462    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -0.9071    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -1.7085   -0.0090 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4072   -1.2702   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -2.1648   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7489   -1.7058   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.3638   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8621    0.2321   -0.3225 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    0.5232   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867    0.1009   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    0.9554   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290    2.3092   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870    3.1291   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    2.6262   -0.0662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7830    1.3121   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881    0.4568   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287    0.7707    0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1318    1.5295    0.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -2.2016    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4791   -0.6538   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4499   -2.5275    0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -3.2270   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -2.4261   -0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423    1.5601   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    2.7947   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    4.1947   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 19  1  0
 19 20  2  0
 17 18  1  0
 19  2  1  0
 18  4  2  0
 12  6  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
M  END
Download

3D SDF for NP0070282 (Pantherinine)


  Mrv1652304282217352D          

 20 23  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  2  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC2=NC3=CC=C(Br)C=C3C3=CC=NC(C1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C15H8BrN3O/c16-7-1-2-11-9(5-7)8-3-4-18-14-13(8)12(19-11)6-10(17)15(14)20/h1-6H,17H2

> <INCHI_KEY>
WUNMOYGATWIMBC-UHFFFAOYSA-N

> <FORMULA>
C15H8BrN3O

> <MOLECULAR_WEIGHT>
326.153

> <EXACT_MASS>
324.985075

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
29.187621546498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-amino-4-bromo-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,8,10,13(17),14-octaen-12-one

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.0789639446666666

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.9325708842287933

> <JCHEM_POLAR_SURFACE_AREA>
68.87

> <JCHEM_REFRACTIVITY>
79.46220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-amino-4-bromo-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,8,10,13(17),14-octaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0070282 (Pantherinine)

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PDB for NP0070282 (Pantherinine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0       8.002   0.000   0.000  0.00  0.00          Br+0
HETATM   20  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    1   12                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    2                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   12                                                       
CONECT   19   17                                                            
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

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3D PDB for NP0070282 (Pantherinine)
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SMILES for NP0070282 (Pantherinine)
NC1=CC2=NC3=CC=C(Br)C=C3C3=CC=NC(C1=O)=C23
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INCHI for NP0070282 (Pantherinine)
InChI=1S/C15H8BrN3O/c16-7-1-2-11-9(5-7)8-3-4-18-14-13(8)12(19-11)6-10(17)15(14)20/h1-6H,17H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H8BrN3O
Average Mass326.1530 Da
Monoisotopic Mass324.98508 Da
IUPAC Name11-amino-4-bromo-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,8,10,13(17),14-octaen-12-one
Traditional Name11-amino-4-bromo-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,8,10,13(17),14-octaen-12-one
CAS Registry NumberNot Available
SMILES
NC1=CC2=NC3=CC=C(Br)C=C3C3=CC=NC(C1=O)=C23
InChI Identifier
InChI=1S/C15H8BrN3O/c16-7-1-2-11-9(5-7)8-3-4-18-14-13(8)12(19-11)6-10(17)15(14)20/h1-6H,17H2
InChI KeyWUNMOYGATWIMBC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aplidium pantherinumAnimalia
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridones. Pyrido[2,3,4-kl]acridones are compounds containing a pyrido[2,3,4-kl]acridine carrying a C=O group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassBenzoquinolines  
Direct ParentPyrido[2,3,4-kl]acridones  
Alternative Parents
Substituents
  • Pyrido[2,3,4-kl]acridone
    • 

  • Pyrido[2,3,4-kl]acridine
    • 

  • Haloquinoline
    • 

  • Diazanaphthalene
    • 

  • Naphthyridine
    • 

  • Aryl ketone
    • 

  • Aryl bromide
    • 

  • Aryl halide
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Ketone
    • 

  • Enamine
    • 

  • Azacycle
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.76ALOGPS
logP2.08ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)0.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.87 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.46 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00028799  
Chemspider ID167140  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192598  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kim J, Pordesimo EO, Toth SI, Schmitz FJ, Van Altena I: Pantherinine, a cytotoxic aromatic alkaloid, and 7-deazainosine from the ascidian Aplidium pantherinum. J Nat Prod. 1993 Oct;56(10):1813-6. doi: 10.1021/np50100a023. [PubMed:8277319  ]