(2R)-2-Amino-4-methylsulfonyl-N-[3-(trifluoromethoxy)phenyl]butanamide

ID: ALA4744809

PubChem CID: 155289362

Max Phase: Preclinical

Molecular Formula: C12H15F3N2O4S

Molecular Weight: 340.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H15F3N2O4S/c1-22(19,20)6-5-10(16)11(18)17-8-3-2-4-9(7-8)21-12(13,14)15/h2-4,7,10H,5-6,16H2,1H3,(H,17,18)/t10-/m1/s1

Standard InChI Key:  SJCAGVRRCBPLMJ-SNVBAGLBSA-N

Molfile:  

 
     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   15.4936   -8.4980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6764   -8.4980    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0850   -9.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8437   -5.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8426   -6.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5506   -6.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2603   -6.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2575   -5.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5488   -4.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1346   -6.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4272   -6.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7191   -6.4597    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4278   -5.2345    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155   -5.6419    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.9686   -6.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6757   -6.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3841   -6.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6744   -5.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0911   -6.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3853   -7.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6783   -7.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9725   -8.9114    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  6
 17 20  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4744809

   ---

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: 340.32

Molecular Weight (Monoisotopic): 340.0705

AlogP: 1.29

#Rotatable Bonds: 6

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: 12.97

CX Basic pKa: 7.44

CX LogP: 0.67

CX LogD: 0.35

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -1.26

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