NP-MRD: Showing NP-Card for streptonigrin (NP0298997)

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Record Information

Version

2.0

Created at

2022-09-10 10:34:55 UTC

Updated at

2022-09-10 10:34:55 UTC

NP-MRD ID

NP0298997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

streptonigrin

Description

streptonigrin is found in Streptomyces rufochromogenes.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102212342D          

 37 40  0  0  0  0            999 V2000
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
   -2.8579    0.8250    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
   -2.8579    0.0000    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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 N   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
   -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
    0.0000   -0.0000    0.0000 N   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
    1.4289    0.8250    0.0000 O   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
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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
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 34 35  1  0  0  0  0
  9 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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   -6.5274   -0.4210   -0.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1910    1.0685   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    1.6798   -1.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9713    0.7865    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6557    0.6211    2.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097    1.0001    3.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    0.3379    3.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3465    0.0890    4.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3790    0.1213    5.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5839   -1.9850   -1.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3386   -3.1735   -1.6087 N   0  0  0  0  0  0  0  0  0  0  0  0
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 16 47  1  0
M  END


  Mrv1652309102212342D          

 37 40  0  0  0  0            999 V2000
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(=O)\C(C=C1)=C1\C(C)=C(NC(=C1N)C1=CC=C2C(=O)C(OC)=C(N)C(=O)C2=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,29H,26-27H2,1-4H3,(H,33,34)/b14-10-

> <INCHI_KEY>
DLWOTOMWYCRPLK-UVTDQMKNSA-N

> <FORMULA>
C25H22N4O8

> <MOLECULAR_WEIGHT>
506.471

> <EXACT_MASS>
506.143763684

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
50.94637000821866

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-[(1Z)-4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene]-3-methyl-1,4-dihydropyridine-2-carboxylic acid

> <JCHEM_LOGP>
-2.8055223019163837

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.402293307122214

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4516443302948194

> <JCHEM_PKA_STRONGEST_BASIC>
2.554910586361566

> <JCHEM_POLAR_SURFACE_AREA>
193.16

> <JCHEM_REFRACTIVITY>
137.95719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-[(1Z)-4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene]-3-methyl-1H-pyridine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.000  -0.000   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       5.335  -0.000   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   36                                                  
CONECT   10    9   11   34                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   22   33                                                  
CONECT   33   32                                                            
CONECT   34   18   10   35                                                  
CONECT   35   34                                                            
CONECT   36    9   37                                                       
CONECT   37   36    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂N₄O₈

Average Mass

506.4710 Da

Monoisotopic Mass

506.14376 Da

IUPAC Name

5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-[(1Z)-4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene]-3-methyl-1,4-dihydropyridine-2-carboxylic acid

Traditional Name

5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-[(1Z)-4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene]-3-methyl-1H-pyridine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(=O)\C(C=C1)=C1\C(C)=C(NC(=C1N)C1=CC=C2C(=O)C(OC)=C(N)C(=O)C2=N1)C(O)=O

InChI Identifier

InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,29H,26-27H2,1-4H3,(H,33,34)/b14-10-

InChI Key

DLWOTOMWYCRPLK-UVTDQMKNSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces rufochromogenes	LOTUS Database	35616633

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	-2.8	ChemAxon
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	2.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	193.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.96 m³·mol⁻¹	ChemAxon
Polarizability	50.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for streptonigrin (NP0298997)

MOL for NP0298997 (streptonigrin)

3D MOL for NP0298997 (streptonigrin)

3D SDF for NP0298997 (streptonigrin)

3D-SDF for NP0298997 (streptonigrin)

PDB for NP0298997 (streptonigrin)

3D PDB for NP0298997 (streptonigrin)

SMILES for NP0298997 (streptonigrin)

INCHI for NP0298997 (streptonigrin)

Structure for NP0298997 (streptonigrin)

3D Structure for NP0298997 (streptonigrin)