4-(2-(5-chlorobenzo[d]oxazol-2-ylthio)acetamido)benzoic acid

ID: ALA4576930

PubChem CID: 15944392

Max Phase: Preclinical

Molecular Formula: C16H11ClN2O4S

Molecular Weight: 362.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CSc1nc2cc(Cl)ccc2o1)Nc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C16H11ClN2O4S/c17-10-3-6-13-12(7-10)19-16(23-13)24-8-14(20)18-11-4-1-9(2-5-11)15(21)22/h1-7H,8H2,(H,18,20)(H,21,22)

Standard InChI Key:  MMHBAEZOYFGKCQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.1758  -12.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1747  -13.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8827  -13.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8809  -12.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5896  -12.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5944  -13.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3788  -13.7317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8588  -13.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3710  -12.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667  -13.8899    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6759  -13.0580    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0804  -12.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8975  -12.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3019  -11.6330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3103  -13.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1191  -11.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5303  -12.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3467  -12.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7520  -11.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3348  -10.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5197  -10.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5711  -11.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9848  -12.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9745  -10.9027    0.0000 O   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  2  0
  8  9  1  0
  9  5  1  0
  2 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 22 24  2  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4576930

   4-({[(5-Chloro-1,3-benzoxazol-2-yl)sulfanyl]acetyl}amino)benzoic acid

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: 362.79

Molecular Weight (Monoisotopic): 362.0128

AlogP: 3.91

#Rotatable Bonds: 5

Polar Surface Area: 92.43

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.16

CX Basic pKa: ┄

CX LogP: 3.49

CX LogD: 0.43

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -2.04

References

1. Ge L, Li KS, Li MM, Xiao P, Hou XB, Chen X, Liu HD, Lin A, Yu X, Ren GJ, Fang H, Sun JP..  (2016)  Identification of a benzo imidazole thiazole derivative as the specific irreversible inhibitor of protein tyrosine phosphatase.,  26  (19): [PMID:27554446] [10.1016/j.bmcl.2016.08.024]

Source

Source(1):

• Scientific Literature