4-Chloro-3'-((2-cyclopropyl-3-oxo-2,3-dihydrobenzo[d]-isothiazol-6-yloxy)methyl)biphenyl-3-carboxylic acid

ID: ALA2179629

PubChem CID: 53390677

Max Phase: Preclinical

Molecular Formula: C24H18ClNO4S

Molecular Weight: 451.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2cccc(COc3ccc4c(=O)n(C5CC5)sc4c3)c2)ccc1Cl

Standard InChI:  InChI=1S/C24H18ClNO4S/c25-21-9-4-16(11-20(21)24(28)29)15-3-1-2-14(10-15)13-30-18-7-8-19-22(12-18)31-26(23(19)27)17-5-6-17/h1-4,7-12,17H,5-6,13H2,(H,28,29)

Standard InChI Key:  RBQZSTHTHNKFHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.2116  -11.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351  -10.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9453  -11.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8102  -10.7627    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.3661  -13.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8935  -11.5836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7144  -11.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247   -9.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4127  -12.2469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.4127  -10.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9219  -10.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4971  -12.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6557  -13.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6557  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6677  -10.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4247  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0764  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2351   -9.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -11.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0764  -13.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247  -11.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9453  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7867  -11.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 23 18  2  0
  3 22  1  0
  3 28  1  0
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 25 23  1  0
 28 29  2  0
 15 14  2  0
  4  3  2  0
  2 12  1  0
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 15  1  1  0
 29 24  1  0
 22 17  2  0
 25 12  2  0
 20 31  1  0
  6 14  1  0
  7 11  1  0
  8 21  1  0
 30  4  1  0
  7  8  1  0
 18 26  1  0
 10 23  1  0
 20 27  1  0
 28  5  1  0
 31 13  1  0
  8 19  1  0
 11 25  1  0
 13 26  1  0
 26  2  2  0
  1 20  2  0
 30 24  2  0
 30 15  1  0
 11 16  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2179629

   Sodium;2-chloro-5-[3-[(2-cyclopropyl-3-oxo-1,2-benzothiazol-6-yl)oxymethyl]phenyl]benzoate

2. Parent:

   

   ALA2179629

   2-Chloro-5-[3-[(2-cyclopropyl-3-oxo-1,2-benzothiazol-6-yl)oxymethyl]phenyl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 451.93

Molecular Weight (Monoisotopic): 451.0645

AlogP: 6.00

#Rotatable Bonds: 6

Polar Surface Area: 68.53

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.99

CX Basic pKa: ┄

CX LogP: 5.52

CX LogD: 2.05

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: -0.83

References

1. Sidique S, Dhanya RP, Sheffler DJ, Nickols HH, Yang L, Dahl R, Mangravita-Novo A, Smith LH, D'Souza MS, Semenova S, Conn PJ, Markou A, Cosford ND..  (2012)  Orally active metabotropic glutamate subtype 2 receptor positive allosteric modulators: structure-activity relationships and assessment in a rat model of nicotine dependence.,  55  (22): [PMID:23009245] [10.1021/jm3005306]

Source

Source(1):

• Scientific Literature