3-(4-(4-Phenylbut-1-yn-1-yl)phenyl)propanoic acid

ID: ALA3787151

PubChem CID: 127033353

Max Phase: Preclinical

Molecular Formula: C19H18O2

Molecular Weight: 278.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1ccc(C#CCCc2ccccc2)cc1

Standard InChI:  InChI=1S/C19H18O2/c20-19(21)15-14-18-12-10-17(11-13-18)9-5-4-8-16-6-2-1-3-7-16/h1-3,6-7,10-13H,4,8,14-15H2,(H,20,21)

Standard InChI Key:  ZNSKQVAHOOOMGL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.8916   -4.9570    0.0000 O   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
    4.9336   -3.1588    0.0000 O   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
    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
   -2.5988    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    2.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    4.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5022    6.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8027    7.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1002    6.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0972    5.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7966    4.4998    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  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 14 19  1  0
  9 20  1  0
 20 21  2  0
  6 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3787151

   ---

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: 278.35

Molecular Weight (Monoisotopic): 278.1307

AlogP: 3.69

#Rotatable Bonds: 5

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.03

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 1.93

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.85

Np Likeness Score: 0.06

References

1. Hansen SV, Christiansen E, Urban C, Hudson BD, Stocker CJ, Due-Hansen ME, Wargent ET, Shimpukade B, Almeida R, Ejsing CS, Cawthorne MA, Kassack MU, Milligan G, Ulven T..  (2016)  Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy.,  59  (6): [PMID:26928019] [10.1021/acs.jmedchem.5b01962]

Source

Source(1):

• Scientific Literature