NP-MRD: Showing NP-Card for Calothrixin B (NP0068622)

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Record Information

Version

2.0

Created at

2022-04-28 13:52:28 UTC

Updated at

2022-04-28 13:52:28 UTC

NP-MRD ID

NP0068622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calothrixin B

Description

7H-Indolo[3,2-j]phenanthridine-7,13(12H)-dione, also known as calothrixin b, belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. Calothrixin B is found in Calothrix sp. 7H-Indolo[3,2-j]phenanthridine-7,13(12H)-dione is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -0.5458    1.5834    1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    0.7718    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222    0.4759    0.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2377    0.9716    0.9443 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770    0.3923    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6330    0.5393    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -0.1810   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0194   -1.0582   -1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468   -1.2087   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197   -0.4743   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -0.4161   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4008   -1.0955   -1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -1.9188   -2.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0097   -0.8176   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -1.4403   -1.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -1.1853   -1.4728 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6402   -0.3117   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9661   -0.0736   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691    0.7957    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.4480    1.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507    1.2443    1.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    0.3603    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3387    0.0950   -0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    1.6692    1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    1.2309    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5443   -0.0643   -0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7174   -1.6078   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2721   -1.8818   -2.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -2.1354   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6930   -0.6090   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4431    0.9713    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390    2.1422    2.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    1.7884    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 11  1  0
 11  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  2  0
  3  2  1  0
  2  1  2  0
  2 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 10 11  1  0
 14 23  1  0
 10  5  1  0
 17 22  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 21 33  1  0
 20 32  1  0
 19 31  1  0
 18 30  1  0
 15 29  1  0
M  END


  Mrv1533004171520512D          

 23 27  0  0  0  0            999 V2000
    2.4676    2.1761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    1.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.9193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2654    1.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0859    1.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220    0.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376   -0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810    0.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760   -0.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428   -0.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -0.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436   -0.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1010    0.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854    1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989    0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  7  1  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 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 15 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0068622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C2=C(NC3=CC=CC=C23)C(=O)C2=C3C=CC=CC3=NC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H10N2O2/c22-18-12-9-20-13-7-3-1-5-10(13)15(12)19(23)17-16(18)11-6-2-4-8-14(11)21-17/h1-9,21H

> <INCHI_KEY>
CCPDIHKLISWESE-UHFFFAOYSA-N

> <FORMULA>
C19H10N2O2

> <MOLECULAR_WEIGHT>
298.301

> <EXACT_MASS>
298.07422757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
31.436273763126465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7H,12H,13H-quinolino[4,3-b]carbazole-7,13-dione

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.0951238466666666

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.826362561322371

> <JCHEM_PKA_STRONGEST_BASIC>
1.2934470495910428

> <JCHEM_POLAR_SURFACE_AREA>
62.82

> <JCHEM_REFRACTIVITY>
86.0363

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12H-quinolino[4,3-b]carbazole-7,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       4.606   4.062   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.234   2.656   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.765   2.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.670   3.743   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.201   3.583   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.829   2.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.360   2.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.988   0.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.084  -0.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.552  -0.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.924   0.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.489  -0.157   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.116  -1.563   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.957   0.003   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.813  -1.029   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.479  -0.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.015  -0.737   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.131   0.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.188   1.800   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.653   2.277   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.798   1.247   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.329   1.409   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22    2   15                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
Calothrixin b	MeSH

Chemical Formula

C₁₉H₁₀N₂O₂

Average Mass

298.3010 Da

Monoisotopic Mass

298.07423 Da

IUPAC Name

7H,12H,13H-quinolino[4,3-b]carbazole-7,13-dione

Traditional Name

12H-quinolino[4,3-b]carbazole-7,13-dione

CAS Registry Number

Not Available

SMILES

O=C1C2=C(NC3=CC=CC=C23)C(=O)C2=C3C=CC=CC3=NC=C12

InChI Identifier

InChI=1S/C19H10N2O2/c22-18-12-9-20-13-7-3-1-5-10(13)15(12)19(23)17-16(18)11-6-2-4-8-14(11)21-17/h1-9,21H

InChI Key

CCPDIHKLISWESE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Calothrix sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Carbazole
Indolecarboxylic acid derivative
Isoquinoline quinone
Indole
Indole or derivatives
Pyridine carboxylic acid or derivatives
Aryl ketone
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Pyrrole
Ketone
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.15	ALOGPS
logP	3.1	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	1.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.04 m³·mol⁻¹	ChemAxon
Polarizability	31.44 Å³	ChemAxon
Number of Rings	5	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

9817721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Calothrixin B (NP0068622)

MOL for NP0068622 (Calothrixin B)

3D MOL for NP0068622 (Calothrixin B)

3D SDF for NP0068622 (Calothrixin B)

3D-SDF for NP0068622 (Calothrixin B)

PDB for NP0068622 (Calothrixin B)

3D PDB for NP0068622 (Calothrixin B)

SMILES for NP0068622 (Calothrixin B)

INCHI for NP0068622 (Calothrixin B)

Structure for NP0068622 (Calothrixin B)

3D Structure for NP0068622 (Calothrixin B)