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

ID: ALA2288989

PubChem CID: 76327472

Max Phase: Preclinical

Molecular Formula: C16H11Cl2N3O3S

Molecular Weight: 396.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1Nc1nnc(COc2ccc(Cl)cc2Cl)s1

Standard InChI:  InChI=1S/C16H11Cl2N3O3S/c17-9-5-6-13(11(18)7-9)24-8-14-20-21-16(25-14)19-12-4-2-1-3-10(12)15(22)23/h1-7H,8H2,(H,19,21)(H,22,23)

Standard InChI Key:  VRDVYHLIEWNMKQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   35.5206   -1.5034    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.1868   -1.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9290   -0.2316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1035   -0.2344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8518   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9721   -1.2684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9905   -2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2855   -2.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3036   -3.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0277   -3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7351   -3.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7136   -2.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4166   -2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1422   -2.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3937   -1.2258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1325   -1.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4228   -1.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7035   -1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9954   -0.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2766   -1.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2665   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9811   -2.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6971   -2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4083   -2.6486    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.5476   -2.6205    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
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288989

   2-[[5-[(2,4-Dichlorophenoxy)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: 396.25

Molecular Weight (Monoisotopic): 394.9898

AlogP: 4.87

#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: 5.68

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -1.97

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