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Showing NP-Card for (-)-Phaitanthrin C (NP0076962)

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Record Information
Version1.0
Created at2022-04-28 22:08:43 UTC
Updated at2022-04-28 22:08:43 UTC
NP-MRD IDNP0076962
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Phaitanthrin C
Description1-Hydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. (-)-Phaitanthrin C is found in Phaius mishmensis. 1-Hydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0076962 ((-)-Phaitanthrin C)


  Mrv1533004241518282D          

 20 23  0  0  0  0            999 V2000
    1.2483   -4.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -5.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
  6 20  2  0  0  0  0
M  END
Download

3D MOL for NP0076962 ((-)-Phaitanthrin C)

     RDKit          3D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -1.2952    2.2142    2.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031    1.3239    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    0.5659    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    0.5709    0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425    1.4452    1.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571   -0.2940    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417   -1.1531   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3698   -1.1620   -0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.2982   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -0.1230   -0.1036 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577    0.8309    0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285    1.1928    1.0586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3221    0.5806    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    0.9581    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6535    0.3336   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880   -0.6460   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -1.0271   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -0.3992   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -0.7583   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175   -1.6500   -1.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794    2.0573    2.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4477   -0.3053    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3785   -1.8180   -1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101   -1.8418   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167    1.7390    1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836    0.6056    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1803   -1.1492   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399   -1.7927   -1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  3  2  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 10  1  0
  3  4  1  0
 10 11  1  0
 10  9  1  0
 18 13  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
M  END
Download

3D SDF for NP0076962 ((-)-Phaitanthrin C)


  Mrv1533004241518282D          

 20 23  0  0  0  0            999 V2000
    1.2483   -4.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -5.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
  6 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0076962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1C(=O)C1=NC3=CC=CC=C3C(=O)N21

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N2O3/c18-11-7-3-6-10-12(11)13(19)14-16-9-5-2-1-4-8(9)15(20)17(10)14/h1-7,18H

> <INCHI_KEY>
WOQXYBJCORZEEE-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O3

> <MOLECULAR_WEIGHT>
264.24

> <EXACT_MASS>
264.053492126

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
26.21626741325611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.742097072

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.096101207701745

> <JCHEM_PKA_STRONGEST_BASIC>
-3.385757623247247

> <JCHEM_POLAR_SURFACE_AREA>
69.97

> <JCHEM_REFRACTIVITY>
73.59909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phaitanthrin C

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0076962 ((-)-Phaitanthrin C)

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PDB for NP0076962 ((-)-Phaitanthrin C)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       2.330  -8.793   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.677  -6.027   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       8.440  -8.029   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.638  -8.292   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.460  -9.822   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    7   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

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3D PDB for NP0076962 ((-)-Phaitanthrin C)
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SMILES for NP0076962 ((-)-Phaitanthrin C)
OC1=CC=CC2=C1C(=O)C1=NC3=CC=CC=C3C(=O)N21
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INCHI for NP0076962 ((-)-Phaitanthrin C)
InChI=1S/C15H8N2O3/c18-11-7-3-6-10-12(11)13(19)14-16-9-5-2-1-4-8(9)15(20)17(10)14/h1-7,18H
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View in JSmol
Synonyms
ValueSource
7-HydroxytryptanthrinChEMBL
Chemical FormulaC15H8N2O3
Average Mass264.2400 Da
Monoisotopic Mass264.05349 Da
IUPAC Name1-hydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione
Traditional Namephaitanthrin C
CAS Registry NumberNot Available
SMILES
OC1=CC=CC2=C1C(=O)C1=NC3=CC=CC=C3C(=O)N21
InChI Identifier
InChI=1S/C15H8N2O3/c18-11-7-3-6-10-12(11)13(19)14-16-9-5-2-1-4-8(9)15(20)17(10)14/h1-7,18H
InChI KeyWOQXYBJCORZEEE-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
Phaius mishmensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic  compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazanaphthalenes  
Sub ClassBenzodiazines  
Direct ParentIndoloquinazolines  
Alternative Parents
Substituents
  • Indoloquinazoline
    • 

  • Indole
    • 

  • Indole or derivatives
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyrimidone
    • 

  • Pyrimidine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Vinylogous acid
    • 

  • Lactam
    • 

  • Ketone
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen 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
logP2.02ALOGPS
logP2.74ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.97 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.6 m³·mol⁻¹ChemAxon
Polarizability26.22 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24970644  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available