methyl 4-(4-(N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamido)piperidin-1-yl)-4-oxobutanoate

ID: ALA4090142

PubChem CID: 137641490

Max Phase: Preclinical

Molecular Formula: C22H25Br2N3O4

Molecular Weight: 555.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCC(=O)N1CCC(N(Cc2ccccc2)C(=O)c2cc(Br)c(Br)[nH]2)CC1

Standard InChI:  InChI=1S/C22H25Br2N3O4/c1-31-20(29)8-7-19(28)26-11-9-16(10-12-26)27(14-15-5-3-2-4-6-15)22(30)18-13-17(23)21(24)25-18/h2-6,13,16,25H,7-12,14H2,1H3

Standard InChI Key:  JKIXNXBDRLCNFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   10.7621   -8.1775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8852   -6.9517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8852   -7.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1803   -8.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4712   -7.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4712   -6.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1803   -6.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5943   -6.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5943   -5.7259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3018   -6.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0547   -7.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7614   -8.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4687   -9.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3467   -8.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0554   -6.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6029   -7.8447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2631   -8.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4637   -9.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0576   -8.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0097   -6.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7173   -6.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4251   -6.5443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7169   -7.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2450   -8.3650    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.1299   -9.9056    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.1327   -6.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4661  -10.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1727  -10.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8817  -10.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8798   -9.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1726   -8.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  1  0
  8  9  2  0
  2  8  1  0
  1  5  1  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
 12 13  1  0
 11 14  1  0
 11 15  2  0
 14 16  1  0
 16 19  1  0
 18 17  1  0
 17 14  2  0
 18 19  2  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 18 25  1  0
 22 26  1  0
 13 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090142

   ---

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: 555.27

Molecular Weight (Monoisotopic): 553.0212

AlogP: 4.13

#Rotatable Bonds: 7

Polar Surface Area: 82.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.94

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -0.92

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