2-(5-((2-chlorophenoxy)methyl)-1,3,4-thiadiazol-2-ylamino)benzoic acid

ID: ALA2288987

PubChem CID: 14491433

Max Phase: Preclinical

Molecular Formula: C16H12ClN3O3S

Molecular Weight: 361.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1Nc1nnc(COc2ccccc2Cl)s1

Standard InChI:  InChI=1S/C16H12ClN3O3S/c17-11-6-2-4-8-13(11)23-9-14-19-20-16(24-14)18-12-7-3-1-5-10(12)15(21)22/h1-8H,9H2,(H,18,20)(H,21,22)

Standard InChI Key:  MKHAEYOPCFKCMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.4106   -2.1243    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0768   -1.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8190   -0.8526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9935   -0.8554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7418   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8621   -1.8894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8805   -2.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1755   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1936   -3.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9178   -4.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6252   -3.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6037   -3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3067   -2.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0324   -3.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2838   -1.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0225   -2.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3128   -1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5933   -2.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8853   -1.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1664   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1563   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8710   -3.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5870   -2.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2982   -3.2696    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 13 14  1  0
 13 15  2  0
 12 13  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288987

   2-[[5-[(2-Chlorophenoxy)methyl]-1,3,4-thiadiazol-2-yl]amino]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: 361.81

Molecular Weight (Monoisotopic): 361.0288

AlogP: 4.21

#Rotatable Bonds: 6

Polar Surface Area: 84.34

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.48

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -1.91

References

1. TIWARI N, DWIVEDI B, NIZAMUDDIN.  (1990)  Synthesis of Some 2-Aryloxymethyl-1, 3, 4-thiadiazolo[2, 3-b]-quinazolin-4-ones and 2-Aryloxymethyl-5-substituted-1, 3, 4-thiadiazolo[3, 2-a]-s-triazin-7-thiones as Potential Biocides,  15  (3): [10.1584/jpestics.15.357]

Source

Source(1):

• Scientific Literature