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

ID: ALA2288990

PubChem CID: 14709600

Max Phase: Preclinical

Molecular Formula: C18H17N3O3S

Molecular Weight: 355.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(OCc2nnc(Nc3ccccc3C(=O)O)s2)cc1C

Standard InChI:  InChI=1S/C18H17N3O3S/c1-11-7-8-13(9-12(11)2)24-10-16-20-21-18(25-16)19-15-6-4-3-5-14(15)17(22)23/h3-9H,10H2,1-2H3,(H,19,21)(H,22,23)

Standard InChI Key:  JQQQPMQJVRREEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.4762   -2.6537    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1424   -2.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8846   -1.3818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0590   -1.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8073   -2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9277   -2.4188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9462   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2412   -3.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -4.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9835   -4.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6909   -4.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6694   -3.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -3.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0982   -3.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3495   -2.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -2.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3782   -2.1535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6588   -2.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318   -2.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216   -3.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9364   -3.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295   -4.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5058   -3.7709    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
 22 24  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288990

   2-[[5-[(3,4-Dimethylphenoxy)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: 355.42

Molecular Weight (Monoisotopic): 355.0991

AlogP: 4.18

#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: 5.50

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -1.79

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