NP-MRD: Showing NP-Card for 4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol (NP0265794)

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Record Information

Version

2.0

Created at

2022-09-08 09:54:36 UTC

Updated at

2022-09-08 09:54:36 UTC

NP-MRD ID

NP0265794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol

Description

4-(4,5-Dibromo-1-methyl-1H-pyrrole-2-carbonyl)-2-imino-1H,2H,4H,5H,6H-imidazo[4,5-b]pyridin-7-ol belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. 4-(4,5-Dibromo-1-methyl-1H-pyrrole-2-carbonyl)-2-imino-1H,2H,4H,5H,6H-imidazo[4,5-b]pyridin-7-ol is an extremely strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.4359    1.5278   -1.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634    1.1820   -0.3319 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604    0.6454   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    0.2669   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2581    0.3202   -2.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -0.1458   -0.9486 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.5907   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -2.0121   -1.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148   -1.9798   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6334   -2.9187   -0.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972   -1.1061    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -0.8478    1.5820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3935    0.1513    2.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956    0.7297    3.4012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3475    0.6006    1.2851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216   -0.1245    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258    0.4822    1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    0.9508    1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512    0.9621    3.6606 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7075    1.3774    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703    2.1045    0.8885 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    2.0714   -1.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870    2.1651   -2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786    0.5864   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.5786   -3.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    0.0561   -2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246   -2.6561   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -2.2916   -2.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -2.8792    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732    0.8923    3.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    0.9944    4.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558    0.0639    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 20  1  0
 20 21  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  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
 13 15  1  0
 15 16  2  0
  3  2  1  0
 16  6  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 17 32  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv1533004191517342D          

 21 23  0  0  0  0            999 V2000
    3.4665    3.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796    3.2955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    3.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222    4.2207    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1196    2.6663    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.7471    2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 14 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
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 15 20  1  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(Br)=C(Br)C=C1C(=O)N1CCC(O)=C2N=C(N)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H11Br2N5O2/c1-18-6(4-5(13)9(18)14)11(21)19-3-2-7(20)8-10(19)17-12(15)16-8/h4,20H,2-3H2,1H3,(H2,15,16)

> <INCHI_KEY>
YHNMNTDKHSRLIT-UHFFFAOYSA-N

> <FORMULA>
C12H11Br2N5O2

> <MOLECULAR_WEIGHT>
417.061

> <EXACT_MASS>
414.927951

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
33.84108019573727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-(4,5-dibromo-1-methyl-1H-pyrrole-2-carbonyl)-4H,5H,6H-imidazo[4,5-b]pyridin-7-ol

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
-1.3324416279243796

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.754167502046535

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.129277271108677

> <JCHEM_PKA_STRONGEST_BASIC>
15.000000000487931

> <JCHEM_POLAR_SURFACE_AREA>
96.21000000000001

> <JCHEM_REFRACTIVITY>
85.8336

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-5H,6H-imidazo[4,5-b]pyridin-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.471   7.182   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.615   6.152   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.122   6.472   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       9.748   7.879   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       9.892   5.138   0.000  0.00  0.00           C+0
HETATM    6 Br   UNK     0      11.423   4.977   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0       8.861   3.994   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.877   0.770   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   11   15                                                  
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₁Br₂N₅O₂

Average Mass

417.0610 Da

Monoisotopic Mass

414.92795 Da

IUPAC Name

2-amino-4-(4,5-dibromo-1-methyl-1H-pyrrole-2-carbonyl)-4H,5H,6H-imidazo[4,5-b]pyridin-7-ol

Traditional Name

2-amino-4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-5H,6H-imidazo[4,5-b]pyridin-7-ol

CAS Registry Number

Not Available

SMILES

CN1C(Br)=C(Br)C=C1C(=O)N1CCC(O)=C2N=C(N)N=C12

InChI Identifier

InChI=1S/C12H11Br2N5O2/c1-18-6(4-5(13)9(18)14)11(21)19-3-2-7(20)8-10(19)17-12(15)16-8/h4,20H,2-3H2,1H3,(H2,15,16)

InChI Key

YHNMNTDKHSRLIT-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, 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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyridines

Sub Class

Not Available

Direct Parent

Imidazopyridines

Alternative Parents

Substituents

Imidazopyridine
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aryl bromide
Aryl halide
N-methylpyrrole
Substituted pyrrole
Imidazole
Heteroaromatic compound
Pyrrole
Alkanolamine
Amidine
Carboxylic acid amidine
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
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	1.23	ALOGPS
logP	-1.3	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.83 m³·mol⁻¹	ChemAxon
Polarizability	33.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol (NP0265794)

MOL for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

3D MOL for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

3D SDF for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

3D-SDF for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

PDB for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

3D PDB for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

SMILES for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

INCHI for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

Structure for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)

3D Structure for NP0265794 (4-(4,5-dibromo-1-methylpyrrole-2-carbonyl)-2-imino-1h,5h,6h-imidazo[4,5-b]pyridin-7-ol)