2-(5-(p-tolyloxymethyl)-1,3,4-thiadiazol-2-ylamino)benzoic acid

ID: ALA2288988

PubChem CID: 14491434

Max Phase: Preclinical

Molecular Formula: C17H15N3O3S

Molecular Weight: 341.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(OCc2nnc(Nc3ccccc3C(=O)O)s2)cc1

Standard InChI:  InChI=1S/C17H15N3O3S/c1-11-6-8-12(9-7-11)23-10-15-19-20-17(24-15)18-14-5-3-2-4-13(14)16(21)22/h2-9H,10H2,1H3,(H,18,20)(H,21,22)

Standard InChI Key:  NTEGBCFENBLNDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   26.1205   -1.5255    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.7872   -1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5293   -0.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7031   -0.2555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4512   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5732   -1.2903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5917   -2.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8861   -2.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9042   -3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6289   -3.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3369   -3.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3153   -2.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0189   -2.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7453   -2.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9961   -1.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7313   -1.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0211   -1.0249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3011   -1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5925   -1.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8730   -1.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8628   -2.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5781   -2.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2946   -2.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1464   -2.6435    0.0000 C   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
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288988

   2-[[5-[(4-Methylphenoxy)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: 341.39

Molecular Weight (Monoisotopic): 341.0834

AlogP: 3.87

#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: 4.98

CX LogD: 1.60

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: -1.76

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