trans-rac-2-(4-(2-chloro-4-(trifluoromethyl)phenoxy)phenyl)-2-(prop-1-ynyl)cyclopropanecarboxylic acid

ID: ALA1777875

PubChem CID: 54580627

Max Phase: Preclinical

Molecular Formula: C20H14ClF3O3

Molecular Weight: 394.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@]1(c2ccc(Oc3ccc(C(F)(F)F)cc3Cl)cc2)C[C@H]1C(=O)O

Standard InChI:  InChI=1S/C20H14ClF3O3/c1-2-9-19(11-15(19)18(25)26)12-3-6-14(7-4-12)27-17-8-5-13(10-16(17)21)20(22,23)24/h3-8,10,15H,11H2,1H3,(H,25,26)/t15-,19+/m0/s1

Standard InChI Key:  KWFJLSULJSAXSS-HNAYVOBHSA-N

Molfile:  

     RDKit          2D

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   15.6486   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6474   -1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3622   -1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0787   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0758   -0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3604    0.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3580    0.8670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9326   -1.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2185   -1.1970    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9320   -2.4351    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2125   -2.0167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7887    0.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5047   -0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5045   -1.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2197   -1.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9336   -1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9278   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2120    0.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6543   -2.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0791   -1.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7914   -1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0833   -2.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6499   -1.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3625   -1.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6459   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6588   -3.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6633   -4.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  2  8  1  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 23  1  0
  8  9  1  0
 23 19  1  6
  4  5  1  0
 24 20  1  1
  8 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 24 23  1  0
 25 24  1  0
 23 25  1  0
  8 11  1  0
  5  6  2  0
  5 12  1  0
  6  1  1  0
 19 26  3  0
 12 13  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1777875

   (1R,2R)-2-[4-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-2-prop-1-ynylcyclopropane-1-carboxylic 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: 394.78

Molecular Weight (Monoisotopic): 394.0584

AlogP: 5.52

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.59

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.34

References

1. Walsh SP, Severino A, Zhou C, He J, Liang GB, Tan CP, Cao J, Eiermann GJ, Xu L, Salituro G, Howard AD, Mills SG, Yang L..  (2011)  3-Substituted 3-(4-aryloxyaryl)-propanoic acids as GPR40 agonists.,  21  (11): [PMID:21514824] [10.1016/j.bmcl.2011.03.114]

Source

Source(1):

• Scientific Literature