4,5-Dibromo-1H-pyrrole-2-carboxylic acid(4-nitrobenzyloxy)-amide

ID: ALA1770182

PubChem CID: 53231759

Max Phase: Preclinical

Molecular Formula: C12H9Br2N3O4

Molecular Weight: 419.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NOCc1ccc([N+](=O)[O-])cc1)c1cc(Br)c(Br)[nH]1

Standard InChI:  InChI=1S/C12H9Br2N3O4/c13-9-5-10(15-11(9)14)12(18)16-21-6-7-1-3-8(4-2-7)17(19)20/h1-5,15H,6H2,(H,16,18)

Standard InChI Key:  OYLMBMALGFKNMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.4917  -10.1041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -9.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -8.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -8.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1610   -9.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888   -8.1657    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -9.8778    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1108  -10.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1161  -10.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -9.6314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181  -10.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352   -9.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7470  -10.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378  -10.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488  -11.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -9.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695  -10.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687  -10.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814  -11.3046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000  -10.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801  -12.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
 10 11  1  0
 11 12  1  0
  4  6  1  0
 12 13  1  0
  4  5  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
 15 18  2  0
  2  3  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
  2  8  1  0
  1  2  1  0
  8  9  2  0
 18 19  1  0
  3  4  1  0
  8 10  1  0
 19 20  2  0
 19 21  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1770182

   4,5-dibromo-N-[(4-nitrophenyl)methoxy]-1H-pyrrole-2-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 419.03

Molecular Weight (Monoisotopic): 416.8960

AlogP: 3.31

#Rotatable Bonds: 5

Polar Surface Area: 97.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.57

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.57

Np Likeness Score: -0.64

References

1. Wang MZ, Xu H, Liu TW, Feng Q, Yu SJ, Wang SH, Li ZM..  (2011)  Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.,  46  (5): [PMID:21356570] [10.1016/j.ejmech.2011.01.031]

Source

Source(1):

• Scientific Literature