NP-MRD: Showing NP-Card for Calothrixin A (NP0068695)

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Record Information

Version

2.0

Created at

2022-04-28 13:57:41 UTC

Updated at

2022-04-28 13:57:41 UTC

NP-MRD ID

NP0068695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calothrixin A

Description

CALOTHRIXIN A 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 A is found in Calothrix sp. CALOTHRIXIN A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 38  0  0  0  0  0  0  0  0999 V2000
   -1.0874   -2.1640   -1.4221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.1835   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569   -0.9417   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -1.7743   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9704   -1.5902   -1.2606 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.8463   -2.4460   -1.9228 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4800   -0.5711   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8622   -0.3750   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3868    0.6705    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    1.5095    0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    1.3473    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    0.3034    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393    0.1392    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134    1.0254    0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    1.9967    1.4319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115    0.7576    0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    1.3622    1.1545 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184    0.7479    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6434    1.0269    1.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6296    0.2259    0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3344   -0.8566   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978   -1.1130   -0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -0.3361   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031   -0.3183   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -2.6200   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4748   -1.0751   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833    0.8182    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9108    2.3455    1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309    2.0290    1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1560    2.2047    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.8756    1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6667    0.4511    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0990   -1.5061   -0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7114   -1.9656   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 24  2  0
 24 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
 24  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
 12  7  1  0
  3 13  1  0
 17 16  1  0
 18 23  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 22 34  1  0
 21 33  1  0
 20 32  1  0
 19 31  1  0
 17 30  1  0
  4 25  1  0
M  CHG  2   5   1   6  -1
M  END


  Mrv1533004171510042D          

 24 28  0  0  0  0            999 V2000
    0.9023    2.5871    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.3867    1.9193    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2073    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    1.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484    2.1761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732   -0.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880   -0.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7724   -0.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3859    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2150    0.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4306    1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400   -0.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038   -0.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3556    0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1061    0.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301    1.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    1.1659    0.0000 C   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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 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
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  2 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0068695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+]1=C2C=CC=CC2=C2C(=O)C3=C(C4=CC=CC=C4N3)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H10N2O3/c22-18-12-9-21(24)14-8-4-2-6-11(14)15(12)19(23)17-16(18)10-5-1-3-7-13(10)20-17/h1-9,20H

> <INCHI_KEY>
CMDAFIAGTOCRGL-UHFFFAOYSA-N

> <FORMULA>
C19H10N2O3

> <MOLECULAR_WEIGHT>
314.3

> <EXACT_MASS>
314.06914219

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
32.46461724766489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,13-dioxo-7H,12H,13H-quinolino[4,3-b]carbazol-5-ium-5-olate

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
0.7243639649999999

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.721179515809334

> <JCHEM_PKA_STRONGEST_BASIC>
-7.707085692491031

> <JCHEM_POLAR_SURFACE_AREA>
76.87

> <JCHEM_REFRACTIVITY>
89.59810000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,13-dioxo-12H-quinolino[4,3-b]carbazol-5-ium-5-olate

> <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       1.684   4.829   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0       2.589   3.583   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       4.120   3.743   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.025   2.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.556   2.656   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.184   4.062   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.460   1.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.833   0.003   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.977  -1.029   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.311  -0.260   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.775  -0.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.920   0.293   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.601   1.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.137   2.277   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.992   1.247   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.301  -0.157   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.674  -1.563   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.397   1.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.865   0.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.238  -0.477   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.706  -0.636   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.198   0.610   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.429   2.017   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.961   2.176   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   10                                                  
CONECT   16    8   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    2   19                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₀N₂O₃

Average Mass

314.3000 Da

Monoisotopic Mass

314.06914 Da

IUPAC Name

7,13-dioxo-7H,12H,13H-quinolino[4,3-b]carbazol-5-ium-5-olate

Traditional Name

7,13-dioxo-12H-quinolino[4,3-b]carbazol-5-ium-5-olate

CAS Registry Number

Not Available

SMILES

[O-][N+]1=C2C=CC=CC2=C2C(=O)C3=C(C4=CC=CC=C4N3)C(=O)C2=C1

InChI Identifier

InChI=1S/C19H10N2O3/c22-18-12-9-21(24)14-8-4-2-6-11(14)15(12)19(23)17-16(18)10-5-1-3-7-13(10)20-17/h1-9,20H

InChI Key

CMDAFIAGTOCRGL-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
Pyridinium
Heteroaromatic compound
Vinylogous amide
Pyrrole
Ketone
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic salt
Organic oxygen compound
Organic cation
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	1.94	ALOGPS
logP	0.72	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.87 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.6 m³·mol⁻¹	ChemAxon
Polarizability	32.46 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

9926867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Calothrixin A (NP0068695)

MOL for NP0068695 (Calothrixin A)

3D MOL for NP0068695 (Calothrixin A)

3D SDF for NP0068695 (Calothrixin A)

3D-SDF for NP0068695 (Calothrixin A)

PDB for NP0068695 (Calothrixin A)

3D PDB for NP0068695 (Calothrixin A)

SMILES for NP0068695 (Calothrixin A)

INCHI for NP0068695 (Calothrixin A)

Structure for NP0068695 (Calothrixin A)

3D Structure for NP0068695 (Calothrixin A)