N-(5-(2,6-dichlorophenyl)-1,3,4-thiadiazol-2-yl)-3-(ethylamino)-4-hydroxybenzamide

ID: ALA3798438

PubChem CID: 127047086

Max Phase: Preclinical

Molecular Formula: C17H14Cl2N4O2S

Molecular Weight: 409.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1cc(C(=O)Nc2nnc(-c3c(Cl)cccc3Cl)s2)ccc1O

Standard InChI:  InChI=1S/C17H14Cl2N4O2S/c1-2-20-12-8-9(6-7-13(12)24)15(25)21-17-23-22-16(26-17)14-10(18)4-3-5-11(14)19/h3-8,20,24H,2H2,1H3,(H,21,23,25)

Standard InChI Key:  VEXADRXIVYFCEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.0312   -5.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7410   -4.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4493   -2.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9487   -2.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7365   -4.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0250   -5.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5257   -5.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548   -6.4297    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8187   -1.7563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -3.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 13 12  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
  6 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 20 21  1  0
 16 22  1  0
 12 23  1  0
 13 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3798438

   ---

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: 409.30

Molecular Weight (Monoisotopic): 408.0215

AlogP: 4.90

#Rotatable Bonds: 5

Polar Surface Area: 87.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: 4.55

CX LogP: 4.28

CX LogD: 4.26

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -1.75

References

1. Lee EC, Futatsugi K, Arcari JT, Bahnck K, Coffey SB, Derksen DR, Kalgutkar AS, Loria PM, Sharma R..  (2016)  Optimization of amide-based EP3 receptor antagonists.,  26  (11): [PMID:27107947] [10.1016/j.bmcl.2016.04.009]

Source

Source(1):

• Scientific Literature