NP-MRD: Showing NP-Card for 5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide (NP0208273)

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Record Information

Version

2.0

Created at

2022-09-05 05:12:19 UTC

Updated at

2022-09-05 05:12:19 UTC

NP-MRD ID

NP0208273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide

Description

5-Bromo-N-[(6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-2,3,4,5,6,7-hexahydro-1H-1,3-benzodiazol-5-yl)methyl]-1-methyl-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. 5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide is found in Astrosclera willeyana. 5-Bromo-N-[(6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-2,3,4,5,6,7-hexahydro-1H-1,3-benzodiazol-5-yl)methyl]-1-methyl-1H-pyrrole-2-carboxamide is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505352D          

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M  END

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 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(Br)=CC=C1C(=O)NCC1CC2=C(N=C(N)N2)C(C1CNC(=O)C1=CC(Br)=CN1)C1=CNC(N)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26Br2N10O2/c1-35-16(2-3-17(35)25)21(37)29-6-10-4-13-19(34-23(27)32-13)18(15-9-31-22(26)33-15)12(10)8-30-20(36)14-5-11(24)7-28-14/h2-3,5,7,9-10,12,18,28H,4,6,8H2,1H3,(H,29,37)(H,30,36)(H3,26,31,33)(H3,27,32,34)

> <INCHI_KEY>
FNIAZVGARFHKIF-UHFFFAOYSA-N

> <FORMULA>
C23H26Br2N10O2

> <MOLECULAR_WEIGHT>
634.337

> <EXACT_MASS>
632.060696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
58.45410662149414

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{[2-amino-4-(2-amino-1H-imidazol-4-yl)-5-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-6-yl]methyl}-5-bromo-1-methyl-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
1.0500324706666662

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.573569306277996

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.936805159921018

> <JCHEM_PKA_STRONGEST_BASIC>
8.948958493786048

> <JCHEM_POLAR_SURFACE_AREA>
188.32

> <JCHEM_REFRACTIVITY>
147.24349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{[2-amino-7-(2-amino-1H-imidazol-4-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-3H-1,3-benzodiazol-5-yl]methyl}-5-bromo-1-methylpyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       9.242  -2.976   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.777  -3.452   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.301  -4.917   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       8.207  -6.163   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       5.761  -4.917   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.286  -3.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.531  -2.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531  -1.007   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.865  -0.237   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       5.198  -0.237   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.713   2.843   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.531   3.613   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.199   3.613   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.619   6.828   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.095   8.293   0.000  0.00  0.00           C+0
HETATM   29 Br   UNK     0       6.190   9.539   0.000  0.00  0.00          Br+0
HETATM   30  C   UNK     0       8.635   8.293   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       9.111   6.828   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.285   6.828   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       1.760   8.293   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.300   8.293   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       4.206   9.539   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       3.776   6.828   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21   32                                                  
CONECT   21   20   12   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
CONECT   32   20   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆Br₂N₁₀O₂

Average Mass

634.3370 Da

Monoisotopic Mass

632.06070 Da

IUPAC Name

N-{[2-amino-4-(2-amino-1H-imidazol-4-yl)-5-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-6-yl]methyl}-5-bromo-1-methyl-1H-pyrrole-2-carboxamide

Traditional Name

N-{[2-amino-7-(2-amino-1H-imidazol-4-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-3H-1,3-benzodiazol-5-yl]methyl}-5-bromo-1-methylpyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

CN1C(Br)=CC=C1C(=O)NCC1CC2=C(N=C(N)N2)C(C1CNC(=O)C1=CC(Br)=CN1)C1=CNC(N)=N1

InChI Identifier

InChI=1S/C23H26Br2N10O2/c1-35-16(2-3-17(35)25)21(37)29-6-10-4-13-19(34-23(27)32-13)18(15-9-31-22(26)33-15)12(10)8-30-20(36)14-5-11(24)7-28-14/h2-3,5,7,9-10,12,18,28H,4,6,8H2,1H3,(H,29,37)(H,30,36)(H3,26,31,33)(H3,27,32,34)

InChI Key

FNIAZVGARFHKIF-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

Species Name	Source	Reference
Astrosclera willeyana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Pyrrole-2-carboxylic acid or derivatives
Pyrrole-2-carboxamide
Aryl bromide
Aryl halide
N-methylpyrrole
Substituted pyrrole
Azole
Imidazole
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen 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	2.74	ALOGPS
logP	1.05	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	188.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.24 m³·mol⁻¹	ChemAxon
Polarizability	58.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

73836170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide (NP0208273)

MOL for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

3D MOL for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

3D SDF for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

3D-SDF for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

PDB for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

3D PDB for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

SMILES for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

INCHI for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

Structure for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)

3D Structure for NP0208273 (5-bromo-n-[(6-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-2-imino-7-(2-imino-1,3-dihydroimidazol-4-yl)-1,3,4,5,6,7-hexahydro-1,3-benzodiazol-5-yl)methyl]-1-methylpyrrole-2-carboxamide)