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

ID: ALA3785764

PubChem CID: 66562289

Max Phase: Preclinical

Molecular Formula: C15H15FO2

Molecular Weight: 246.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H15FO2/c1-3-11(2)4-5-12-6-7-13(14(16)10-12)8-9-15(17)18/h3,6-7,10H,8-9H2,1-2H3,(H,17,18)/b11-3+

Standard InChI Key:  ZHOWKHLSVSSENE-QDEBKDIKSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    5.2024   -2.6932    0.0000 O   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
    3.8990   -0.7455    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
    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
   -6.2373    2.4009    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
   -6.2385    5.1020    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
    6.2387   -0.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
  8 15  1  0
 15 16  2  0
  5 16  1  0
 16 17  1  0
  2 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3785764

   3-[2-fluoro-4-[(E)-3-methylpent-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: 246.28

Molecular Weight (Monoisotopic): 246.1056

AlogP: 3.16

#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: 3.96

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: -0.11

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