3-(2-Fluoro-4-(3-methylbut-3-en-1-yn-1-yl)phenyl)propanoic acid

ID: ALA3787463

PubChem CID: 66562287

Max Phase: Preclinical

Molecular Formula: C14H13FO2

Molecular Weight: 232.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C#Cc1ccc(CCC(=O)O)c(F)c1

Standard InChI:  InChI=1S/C14H13FO2/c1-10(2)3-4-11-5-6-12(13(15)9-11)7-8-14(16)17/h5-6,9H,1,7-8H2,2H3,(H,16,17)

Standard InChI Key:  FBUXBMCEXUKNSO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    6.2379   -2.4019    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
    3.8985   -2.2508    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
    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
    0.0000    2.7000    0.0000 F   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
   -2.6003    1.4977    0.0000 C   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
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2387    0.8917    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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -4.2012    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  3  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9 15  1  0
 15 16  2  0
  5 16  1  0
  2 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3787463

   3-[2-Fluoro-4-(3-methylbut-3-en-1-ynyl)phenyl]propanoic 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: 232.25

Molecular Weight (Monoisotopic): 232.0900

AlogP: 2.77

#Rotatable Bonds: 3

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: 3.62

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 0.23

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.81

Np Likeness Score: -0.09

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