3-(4-(4,5-dibromo-1H-pyrrole-2-carbonyl)piperazin-1-yl)-3-oxopropanoic acid

ID: ALA4100792

PubChem CID: 137659340

Max Phase: Preclinical

Molecular Formula: C12H13Br2N3O4

Molecular Weight: 423.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(=O)N1CCN(C(=O)c2cc(Br)c(Br)[nH]2)CC1

Standard InChI:  InChI=1S/C12H13Br2N3O4/c13-7-5-8(15-11(7)14)12(21)17-3-1-16(2-4-17)9(18)6-10(19)20/h5,15H,1-4,6H2,(H,19,20)

Standard InChI Key:  ASXCSKZSKOPOBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.2979   -2.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2979   -3.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0032   -3.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7085   -3.5412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7085   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0032   -2.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5890   -2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8825   -2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5866   -1.5003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1311   -2.3962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5861   -3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9968   -3.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7956   -3.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7731   -2.9221    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.6667   -4.4592    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.4156   -3.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4144   -4.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1239   -3.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8310   -3.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5393   -3.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8298   -4.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  8  2  0
 11 14  1  0
 12 15  1  0
  4 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100792

   ---

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: 423.06

Molecular Weight (Monoisotopic): 420.9273

AlogP: 1.30

#Rotatable Bonds: 3

Polar Surface Area: 93.71

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.49

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: -2.90

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: -0.14

References

1. Jukič M, Ilaš J, Brvar M, Kikelj D, Cesar J, Anderluh M..  (2017)  Linker-switch approach towards new ATP binding site inhibitors of DNA gyrase B.,  125  [PMID:27689732] [10.1016/j.ejmech.2016.09.040]

Source

Source(1):

• Scientific Literature