3-(4-((2-Methoxy-5-(trifluoromethyl)benzyl)oxy)-3-methylphenyl)propanoic acid

ID: ALA4065397

PubChem CID: 137633536

Max Phase: Preclinical

Molecular Formula: C19H19F3O4

Molecular Weight: 368.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(F)(F)F)cc1COc1ccc(CCC(=O)O)cc1C

Standard InChI:  InChI=1S/C19H19F3O4/c1-12-9-13(4-8-18(23)24)3-6-16(12)26-11-14-10-15(19(20,21)22)5-7-17(14)25-2/h3,5-7,9-10H,4,8,11H2,1-2H3,(H,23,24)

Standard InChI Key:  UUOBFCXKSUXTJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   31.2758  -14.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9733  -14.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6926  -14.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7154  -13.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0132  -13.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2968  -13.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5994  -13.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4336  -13.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1304  -13.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8485  -13.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5453  -13.5767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8698  -12.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5572  -14.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8609  -14.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1423  -14.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4500  -14.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7318  -14.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7090  -15.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4102  -15.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1255  -15.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4739  -13.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1932  -12.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3907  -16.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6735  -17.0449    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.0885  -17.0787    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.3830  -17.4664    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  1 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 16 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4065397

   ---

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: 368.35

Molecular Weight (Monoisotopic): 368.1235

AlogP: 4.62

#Rotatable Bonds: 7

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.24

CX Basic pKa: ┄

CX LogP: 4.86

CX LogD: 1.85

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -0.66

References

1. Sparks SM, Aquino C, Banker P, Collins JL, Cowan D, Diaz C, Dock ST, Hertzog DL, Liang X, Swiger ED, Yuen J, Chen G, Jayawickreme C, Moncol D, Nystrom C, Rash V, Rimele T, Roller S, Ross S..  (2017)  Exploration of phenylpropanoic acids as agonists of the free fatty acid receptor 4 (FFA4): Identification of an orally efficacious FFA4 agonist.,  27  (5): [PMID:28148462] [10.1016/j.bmcl.2017.01.034]

Source

Source(1):

• Scientific Literature