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

ID: ALA4094273

PubChem CID: 137653061

Max Phase: Preclinical

Molecular Formula: C16H21Br2N3O4

Molecular Weight: 479.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21Br2N3O4/c17-11-7-12(21-14(11)18)16(25)20-8-9-1-3-10(4-2-9)15(24)19-6-5-13(22)23/h7,9-10,21H,1-6,8H2,(H,19,24)(H,20,25)(H,22,23)/t9-,10-

Standard InChI Key:  WZAHTXDADONUQM-MGCOHNPYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    6.8474   -8.2072    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -7.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9642   -7.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0352   -6.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2835   -6.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475   -6.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310   -6.6821    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.7334   -6.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7203   -5.2197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4489   -6.4308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1513   -6.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8668   -6.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8799   -7.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5954   -7.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2936   -7.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2805   -6.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5650   -5.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0091   -7.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7115   -7.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0223   -8.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7378   -8.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7550   -9.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4712  -10.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4885  -10.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1701   -9.5991    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
 10 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 15 18  1  6
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094273

   ---

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: 479.17

Molecular Weight (Monoisotopic): 476.9899

AlogP: 2.67

#Rotatable Bonds: 7

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: 4.45

CX Basic pKa: ┄

CX LogP: 1.75

CX LogD: -1.10

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: -0.34

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