methyl 3-(4-(4,5-dibromo-1H-pyrrole-2-carboxamido)piperidin-1-yl)-3-oxopropanoate

ID: ALA4098045

PubChem CID: 137658742

Max Phase: Preclinical

Molecular Formula: C14H17Br2N3O4

Molecular Weight: 451.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC(=O)N1CCC(NC(=O)c2cc(Br)c(Br)[nH]2)CC1

Standard InChI:  InChI=1S/C14H17Br2N3O4/c1-23-12(21)7-11(20)19-4-2-8(3-5-19)17-14(22)10-6-9(15)13(16)18-10/h6,8,18H,2-5,7H2,1H3,(H,17,22)

Standard InChI Key:  OFBUFZKGPLLWLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8696   -6.8932    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5328   -6.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -6.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7943   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -5.3370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -5.1116    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.6157   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0242   -5.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0242   -6.7135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8456   -6.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -7.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755   -7.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4841   -6.7135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3054   -6.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7140   -6.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7152   -7.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5324   -7.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9421   -8.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9398   -6.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5347   -8.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  2  6  2  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098045

   ---

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: 451.12

Molecular Weight (Monoisotopic): 448.9586

AlogP: 1.82

#Rotatable Bonds: 4

Polar Surface Area: 91.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.97

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.42

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