(2S)-2-Amino-3-methylsulfonyl-N-[3-(trifluoromethoxy)phenyl]propanamide

ID: ALA4776312

PubChem CID: 135388266

Max Phase: Preclinical

Molecular Formula: C11H13F3N2O4S

Molecular Weight: 326.30

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H13F3N2O4S/c1-21(18,19)6-9(15)10(17)16-7-3-2-4-8(5-7)20-11(12,13)14/h2-5,9H,6,15H2,1H3,(H,16,17)/t9-/m1/s1

Standard InChI Key:  PYZPDUSQAFMYLL-SECBINFHSA-N

Molfile:  

 
     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    7.6162   -6.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2079   -7.5328    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0326   -7.5282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -5.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9180   -5.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6329   -6.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3492   -5.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -5.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6310   -4.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -6.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -5.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745   -6.3002    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899   -5.0634    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -5.4747    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643   -6.3003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -5.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931   -6.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768   -5.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4945   -7.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2070   -5.8845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2108   -8.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 17 20  1  6
 19  2  1  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776312

   ---

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: 326.30

Molecular Weight (Monoisotopic): 326.0548

AlogP: 0.90

#Rotatable Bonds: 5

Polar Surface Area: 98.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.92

CX Basic pKa: 6.51

CX LogP: 0.61

CX LogD: 0.56

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -1.44

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