3-((cis)-4-(4,5-dibromo-1H-pyrrole-2-carboxamido)cyclohexane-1-carboxamido)propanoic acid

ID: ALA4090861

PubChem CID: 137644520

Max Phase: Preclinical

Molecular Formula: C15H19Br2N3O4

Molecular Weight: 465.14

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H19Br2N3O4/c16-10-7-11(20-13(10)17)15(24)19-9-3-1-8(2-4-9)14(23)18-6-5-12(21)22/h7-9,20H,1-6H2,(H,18,23)(H,19,24)(H,21,22)/t8-,9+

Standard InChI Key:  WTPYNPGLNUVEAV-DTORHVGOSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.7983   -6.5886    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -6.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -6.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7190   -5.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -5.0366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -5.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -4.8111    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.5362   -5.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9447   -4.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9447   -6.4089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7619   -6.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9877   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3963   -6.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9877   -5.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705   -5.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135   -6.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6221   -5.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6221   -7.1139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4393   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8479   -7.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6651   -7.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0760   -8.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0772   -7.1152    0.0000 O   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  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090861

   ---

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: 2.42

#Rotatable Bonds: 6

Polar Surface Area: 111.29

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.46

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: -1.40

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -0.51

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