2-(([1,1'-Biphenyl]-4-ylmethyl)amino)benzo[d]isothiazol-3(2H)-one

ID: ALA4553365

PubChem CID: 155555609

Max Phase: Preclinical

Molecular Formula: C20H16N2OS

Molecular Weight: 332.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ccccc2sn1NCc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C20H16N2OS/c23-20-18-8-4-5-9-19(18)24-22(20)21-14-15-10-12-17(13-11-15)16-6-2-1-3-7-16/h1-13,21H,14H2

Standard InChI Key:  BYSVIEOCSRECGJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.1880   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1869   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8949   -4.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8932   -2.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6018   -3.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6020   -3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3850   -4.2145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.8687   -3.5484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3846   -2.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6369   -2.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6859   -3.5481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0948   -4.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9119   -4.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3180   -4.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1345   -4.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5436   -4.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1304   -3.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3153   -3.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3608   -4.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7664   -4.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5828   -4.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9910   -4.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5769   -3.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7618   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553365

   ---

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: 332.43

Molecular Weight (Monoisotopic): 332.0983

AlogP: 4.47

#Rotatable Bonds: 4

Polar Surface Area: 34.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.54

CX LogP: 4.66

CX LogD: 4.66

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.60

Np Likeness Score: -0.77

References

1. Castelli R, Scalvini L, Vacondio F, Lodola A, Anselmi M, Vezzosi S, Carmi C, Bassi M, Ferlenghi F, Rivara S, Møller IR, Rand KD, Daglian J, Wei D, Dotsey EY, Ahmed F, Jung KM, Stella N, Singh S, Mor M, Piomelli D..  (2020)  Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines.,  63  (3): [PMID:31714779] [10.1021/acs.jmedchem.9b01679]

Source

Source(1):

• Scientific Literature