(2S,3S)-2-(3'-chloro-[1,1'-biphenyl]-3-ylsulfonamido)-N-hydroxy-3-methylpentanamide

ID: ALA4781728

PubChem CID: 162664312

Max Phase: Preclinical

Molecular Formula: C18H21ClN2O4S

Molecular Weight: 396.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NS(=O)(=O)c1cccc(-c2cccc(Cl)c2)c1)C(=O)NO

Standard InChI:  InChI=1S/C18H21ClN2O4S/c1-3-12(2)17(18(22)20-23)21-26(24,25)16-9-5-7-14(11-16)13-6-4-8-15(19)10-13/h4-12,17,21,23H,3H2,1-2H3,(H,20,22)/t12-,17-/m0/s1

Standard InChI Key:  RECZYEAPUDJHSN-SJCJKPOMSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   13.4837   -2.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8964   -3.4793    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.3048   -2.7669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7859   -6.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7848   -7.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4928   -7.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2025   -7.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1997   -6.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4911   -5.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4858   -5.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1939   -4.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1918   -3.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4824   -3.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7735   -3.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7791   -4.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6072   -3.8861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3134   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0226   -3.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7288   -3.4695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0257   -4.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4381   -3.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3103   -2.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0165   -2.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0134   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6011   -2.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9109   -7.5659    0.0000 Cl  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
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  9 10  1  0
 12  2  1  0
  2 16  1  0
 17 16  1  1
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  1
  7 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781728

   ---

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: 396.90

Molecular Weight (Monoisotopic): 396.0911

AlogP: 3.21

#Rotatable Bonds: 7

Polar Surface Area: 95.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.69

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -1.12

References

1. Thompson JC,Dao WT,Ku A,Rodriguez-Beltran SL,Amezcua M,Palomino AY,Lien T,Salzameda NT.  (2020)  Synthesis and activity of isoleucine sulfonamide derivatives as novel botulinum neurotoxin serotype A light chain inhibitors.,  28  (18): [PMID:32828426] [10.1016/j.bmc.2020.115659]

Source

Source(1):

• Scientific Literature