(3R)-3-Amino-4-oxo-4-[3-(trifluoromethoxy)anilino]butanoic acid

ID: ALA4755686

PubChem CID: 155289363

Max Phase: Preclinical

Molecular Formula: C11H11F3N2O4

Molecular Weight: 292.21

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N[C@H](CC(=O)O)C(=O)Nc1cccc(OC(F)(F)F)c1

Standard InChI:  InChI=1S/C11H11F3N2O4/c12-11(13,14)20-7-3-1-2-6(4-7)16-10(19)8(15)5-9(17)18/h1-4,8H,5,15H2,(H,16,19)(H,17,18)/t8-/m1/s1

Standard InChI Key:  LHAPJSHUQJWWEP-MRVPVSSYSA-N

Molfile:  

 
     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   28.6127   -4.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6115   -5.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3196   -5.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0292   -5.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0264   -4.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3178   -4.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9035   -5.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1961   -5.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4881   -5.9191    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.1967   -4.6938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.4844   -5.1013    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.7376   -5.9192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4446   -5.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1530   -5.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4434   -4.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8601   -5.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1543   -6.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4472   -7.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4485   -7.9610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7389   -6.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  6
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755686

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 292.21

Molecular Weight (Monoisotopic): 292.0671

AlogP: 1.33

#Rotatable Bonds: 5

Polar Surface Area: 101.65

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.15

CX Basic pKa: 8.37

CX LogP: -0.62

CX LogD: -0.66

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: -0.85

References

1. Yamada Y,Takashima H,Walmsley DL,Ushiyama F,Matsuda Y,Kanazawa H,Yamaguchi-Sasaki T,Tanaka-Yamamoto N,Yamagishi J,Kurimoto-Tsuruta R,Ogata Y,Ohtake N,Angove H,Baker L,Harris R,Macias A,Robertson A,Surgenor A,Watanabe H,Nakano K,Mima M,Iwamoto K,Okada A,Takata I,Hitaka K,Tanaka A,Fujita K,Sugiyama H,Hubbard RE.  (2020)  Fragment-Based Discovery of Novel Non-Hydroxamate LpxC Inhibitors with Antibacterial Activity.,  63  (23): [PMID:33210531] [10.1021/acs.jmedchem.0c01215]

Source

Source(1):

• Scientific Literature