3-[4-({5-[(3,4-Difluorophenyl)carbamoyl]-1,3,4-thiadiazol-2-yl}methoxy)phenyl]propanoic acid

ID: ALA3805952

PubChem CID: 127050770

Max Phase: Preclinical

Molecular Formula: C19H15F2N3O4S

Molecular Weight: 419.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1ccc(OCc2nnc(C(=O)Nc3ccc(F)c(F)c3)s2)cc1

Standard InChI:  InChI=1S/C19H15F2N3O4S/c20-14-7-4-12(9-15(14)21)22-18(27)19-24-23-16(29-19)10-28-13-5-1-11(2-6-13)3-8-17(25)26/h1-2,4-7,9H,3,8,10H2,(H,22,27)(H,25,26)

Standard InChI Key:  YCKOJEXQUBDOSS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.8933   -3.7570    0.0000 C   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
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916   -4.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   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
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517    0.8722    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    2.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054    3.2859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554    1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0451    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6536    0.4552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7522    2.7967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1458    0.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7560   -1.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2478   -1.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1295   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5195    1.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0277    1.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7358   -2.3283    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3229   -0.1440    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 14 18  1  0
 19 20  1  0
 19 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 20 22  1  0
 18 19  1  0
 13 15  1  0
  9 12  1  0
  3  6  1  0
 24 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805952

   ---

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: 419.41

Molecular Weight (Monoisotopic): 419.0751

AlogP: 3.66

#Rotatable Bonds: 8

Polar Surface Area: 101.41

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.84

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: -0.02

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.86

References

1. Krasavin M, Lukin A, Zhurilo N, Kovalenko A, Zahanich I, Zozulya S, Moore D, Tikhonova IG..  (2016)  Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold.,  24  (13): [PMID:27229618] [10.1016/j.bmc.2016.04.065]

Source

Source(1):

• Scientific Literature