4,5-Dibromo-1H-pyrrole-2-carboxylic acid(benzo[1,3]dioxol-5-ylmethoxy)-amide

ID: ALA1771520

PubChem CID: 53231637

Max Phase: Preclinical

Molecular Formula: C13H10Br2N2O4

Molecular Weight: 418.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NOCc1ccc2c(c1)OCO2)c1cc(Br)c(Br)[nH]1

Standard InChI:  InChI=1S/C13H10Br2N2O4/c14-8-4-9(16-12(8)15)13(18)17-21-5-7-1-2-10-11(3-7)20-6-19-10/h1-4,16H,5-6H2,(H,17,18)

Standard InChI Key:  ALIHIYLQBMQXBC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.7792   -5.6041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -5.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -4.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1917   -4.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4485   -5.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -3.6657    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2327   -5.3778    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036   -6.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -5.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306   -5.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7477   -5.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595   -5.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4503   -6.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613   -6.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -5.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812   -6.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694   -6.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -5.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6707   -5.3046    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
  3  4  1  0
  8 10  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1771520

   N-(1,3-benzodioxol-5-ylmethoxy)-4,5-dibromo-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: 418.04

Molecular Weight (Monoisotopic): 415.9007

AlogP: 3.13

#Rotatable Bonds: 4

Polar Surface Area: 72.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.57

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: -0.02

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