methyl ((cis)-4-(4,5-dibromo-1H-pyrrole-2-carboxamido)cyclohexane-1-carbonyl)glycinate

ID: ALA4097861

PubChem CID: 137657549

Max Phase: Preclinical

Molecular Formula: C15H19Br2N3O4

Molecular Weight: 465.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CNC(=O)[C@H]1CC[C@@H](NC(=O)c2cc(Br)c(Br)[nH]2)CC1

Standard InChI:  InChI=1S/C15H19Br2N3O4/c1-24-12(21)7-18-14(22)8-2-4-9(5-3-8)19-15(23)11-6-10(16)13(17)20-11/h6,8-9,20H,2-5,7H2,1H3,(H,18,22)(H,19,23)/t8-,9+

Standard InChI Key:  SNYXZQOMVVTBMC-DTORHVGOSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    7.9557   -7.8309    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.6148   -7.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3961   -7.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8763   -6.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3961   -6.2789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6148   -6.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -6.0534    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.6935   -6.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1021   -6.2330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1021   -7.6512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9193   -7.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3279   -8.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1451   -8.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5537   -7.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1451   -6.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3279   -6.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3708   -7.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7794   -6.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7794   -8.3562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5966   -8.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0052   -9.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8224   -9.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5966   -9.7743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7794   -9.7743    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
 11 10  1  6
 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  6
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097861

   ---

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: 465.14

Molecular Weight (Monoisotopic): 462.9742

AlogP: 2.12

#Rotatable Bonds: 5

Polar Surface Area: 100.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.87

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -0.63

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