(S)-2-Amino-3-hydroxy-N-(3-(trifluoromethoxy)phenyl)propanamide

ID: ALA4742289

PubChem CID: 142480020

Max Phase: Preclinical

Molecular Formula: C10H11F3N2O3

Molecular Weight: 264.20

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H11F3N2O3/c11-10(12,13)18-7-3-1-2-6(4-7)15-9(17)8(14)5-16/h1-4,8,16H,5,14H2,(H,15,17)/t8-/m0/s1

Standard InChI Key:  QKKNXONMXNVCIX-QMMMGPOBSA-N

Molfile:  

 
     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   19.5121   -1.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5110   -2.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2190   -2.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9287   -2.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9259   -1.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2172   -0.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8029   -2.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0956   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3875   -2.4852    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.0962   -1.2600    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.3839   -1.6674    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.6370   -2.4853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3441   -2.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0524   -2.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3428   -1.2584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0537   -3.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7621   -3.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7595   -2.0734    0.0000 N   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  0
 16 17  1  0
 14 18  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4742289

   ---

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: 264.20

Molecular Weight (Monoisotopic): 264.0722

AlogP: 0.84

#Rotatable Bonds: 4

Polar Surface Area: 84.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.88

CX Basic pKa: 7.69

CX LogP: 1.24

CX LogD: 0.77

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.75

Np Likeness Score: -1.00

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