(2R)-2-Amino-3-(methanesulfonamido)-N-[3-(trifluoromethoxy)phenyl]propanamide

ID: ALA4759491

PubChem CID: 135387410

Max Phase: Preclinical

Molecular Formula: C11H14F3N3O4S

Molecular Weight: 341.31

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H14F3N3O4S/c1-22(19,20)16-6-9(15)10(18)17-7-3-2-4-8(5-7)21-11(12,13)14/h2-5,9,16H,6,15H2,1H3,(H,17,18)/t9-/m1/s1

Standard InChI Key:  GUDXLGCTHDABJB-SECBINFHSA-N

Molfile:  

 
     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   23.9820   -8.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1571   -8.0913    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.5695   -8.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2974   -4.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2963   -5.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0111   -6.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7275   -5.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7247   -4.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0093   -4.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5816   -6.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8675   -5.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1527   -6.0337    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.8681   -4.7967    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.1490   -5.2080    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.4426   -6.0338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1563   -5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8715   -6.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1550   -4.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5852   -5.6179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8727   -6.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1590   -7.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4465   -8.5086    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:

   

   ALA4759491

   ---

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: 341.31

Molecular Weight (Monoisotopic): 341.0657

AlogP: 0.40

#Rotatable Bonds: 6

Polar Surface Area: 110.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.26

CX Basic pKa: 7.23

CX LogP: 0.45

CX LogD: 0.22

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -1.46

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