NP-MRD: Showing NP-Card for 2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one (NP0303780)

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Record Information

Version

2.0

Created at

2022-09-10 18:25:16 UTC

Updated at

2022-09-10 18:25:16 UTC

NP-MRD ID

NP0303780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one

Description

2,3-Dibromo-4-(2-imino-3-methyl-2,3-dihydro-1H-imidazol-4-yl)-1H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. Based on a literature review very few articles have been published on 2,3-dibromo-4-(2-imino-3-methyl-2,3-dihydro-1H-imidazol-4-yl)-1H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.0348    1.5759   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673    0.7510   -0.4780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597    0.8472   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    1.9984   -0.5828 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122    1.6873   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    0.3462   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -0.3451   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2881   -1.6301   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5018   -2.4773   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -1.8358   -1.1002 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2143   -0.5806   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760   -0.2898   -1.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6295    0.3845    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    1.3066    0.8423 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.9670    1.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8520    3.3703    2.8626 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1495    1.4676    1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755    1.8943    2.3403 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    0.4893    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -0.1660   -0.1410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964   -1.5092    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9488    2.9185   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4026    2.4425   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -2.0428   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -2.6319    0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -3.4221   -0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0245   -2.3796   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125    1.4447    0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8399   -1.4326    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -2.1111   -0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2520   -2.0373    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20  3  1  0
  3  2  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  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 19  2  0
 19 17  1  0
 17 18  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
  6 20  1  0
 19  7  1  0
 14 13  1  0
 21 29  1  0
 21 30  1  0
 21 31  1  0
  2  1  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
M  END


  Mrv1652309102220252D          

 20 22  0  0  0  0            999 V2000
    4.5335    2.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    2.1470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104    1.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844    2.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    3.6138    0.0000 N   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 16  2  0  0  0  0
  4 16  1  0  0  0  0
  3 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0303780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=N)NC=C1C1=CCNC(=O)C2=C1C(Br)=C(Br)N2

> <INCHI_IDENTIFIER>
InChI=1S/C12H11Br2N5O/c1-19-6(4-17-12(19)15)5-2-3-16-11(20)9-7(5)8(13)10(14)18-9/h2,4,18H,3H2,1H3,(H2,15,17)(H,16,20)

> <INCHI_KEY>
OFVTZRHCBUKTFP-UHFFFAOYSA-N

> <FORMULA>
C12H11Br2N5O

> <MOLECULAR_WEIGHT>
401.062

> <EXACT_MASS>
398.933036

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
31.44113601683719

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dibromo-4-(2-imino-3-methyl-2,3-dihydro-1H-imidazol-4-yl)-1H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

> <JCHEM_LOGP>
0.7960121349999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.01952299789902

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.843779079591483

> <JCHEM_PKA_STRONGEST_BASIC>
5.860602614132643

> <JCHEM_POLAR_SURFACE_AREA>
84.01

> <JCHEM_REFRACTIVITY>
95.5474

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dibromo-4-(2-imino-3-methyl-1H-imidazol-4-yl)-1H,6H,7H-pyrrolo[2,3-c]azepin-8-one

> <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       8.463   3.870   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.929   4.008   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.760  -1.771   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.590  -1.629   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       1.144  -0.384   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       3.114   2.327   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.499   3.453   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.637   4.987   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.139   5.330   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.744   6.746   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10    4                                                  
CONECT   17    3   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₁Br₂N₅O

Average Mass

401.0620 Da

Monoisotopic Mass

398.93304 Da

IUPAC Name

2,3-dibromo-4-(2-imino-3-methyl-2,3-dihydro-1H-imidazol-4-yl)-1H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

Traditional Name

2,3-dibromo-4-(2-imino-3-methyl-1H-imidazol-4-yl)-1H,6H,7H-pyrrolo[2,3-c]azepin-8-one

CAS Registry Number

Not Available

SMILES

CN1C(=N)NC=C1C1=CCNC(=O)C2=C1C(Br)=C(Br)N2

InChI Identifier

InChI=1S/C12H11Br2N5O/c1-19-6(4-17-12(19)15)5-2-3-16-11(20)9-7(5)8(13)10(14)18-9/h2,4,18H,3H2,1H3,(H2,15,17)(H,16,20)

InChI Key

OFVTZRHCBUKTFP-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 pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Pyrroloazepine
2-heteroaryl carboxamide
1,2,5-trisubstituted-imidazole
Trisubstituted imidazole
Azepine
Aminoimidazole
Aryl bromide
Aryl halide
N-substituted imidazole
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azole
Imidazole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Organic oxide
Organic nitrogen compound
Organohalogen compound
Organobromide
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
Primary 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	0.8	ChemAxon
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	5.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	84.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.55 m³·mol⁻¹	ChemAxon
Polarizability	31.44 Å³	ChemAxon
Number of Rings	3	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

29215183

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71495033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one (NP0303780)

MOL for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D MOL for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D SDF for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D-SDF for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

PDB for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D PDB for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

SMILES for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

INCHI for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

Structure for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D Structure for NP0303780 (2,3-dibromo-4-(2-imino-3-methyl-1h-imidazol-4-yl)-1h,6h,7h-pyrrolo[2,3-c]azepin-8-one)