(S)-4-((2-(4,5-dibromo-1H-pyrrole-2-carboxamido)-3-(4-hydroxyphenyl)propanamido)methyl)benzoic acid

ID: ALA5281268

Max Phase: Preclinical

Molecular Formula: C22H19Br2N3O5

Molecular Weight: 565.22

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)c2cc(Br)c(Br)[nH]2)cc1

Standard InChI:  InChI=1S/C22H19Br2N3O5/c23-16-10-18(26-19(16)24)21(30)27-17(9-12-3-7-15(28)8-4-12)20(29)25-11-13-1-5-14(6-2-13)22(31)32/h1-8,10,17,26,28H,9,11H2,(H,25,29)(H,27,30)(H,31,32)/t17-/m0/s1

Standard InChI Key:  NPFVTDFFMCQGEY-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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   -1.0734   -0.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849   -0.5889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4964   -0.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -0.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -1.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0971   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9582   -0.2551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292   -0.8651    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -2.2881    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4964    0.6432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -0.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497   -0.1783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -1.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -0.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7730    0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1945    0.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9061    1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9061    1.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177    0.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    1.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3616    1.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482    2.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0599    1.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527    0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7714    2.2879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
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  6  5  2  0
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  4 12  2  0
  2 13  1  0
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 18 17  2  0
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 20 23  1  0
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  1 26  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281268

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 565.22

Molecular Weight (Monoisotopic): 562.9691

AlogP: 3.60

#Rotatable Bonds: 8

Polar Surface Area: 131.52

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 0.36

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.02

References

1. Dighe SN, Collet TA..  (2020)  Recent advances in DNA gyrase-targeted antimicrobial agents.,  199  [PMID:32460040] [10.1016/j.ejmech.2020.112326]

Source

Source(1):

• Scientific Literature