(Z)-3-(2-Fluoro-4-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)phenyl)propanoic acid

ID: ALA3785413

PubChem CID: 66562391

Max Phase: Preclinical

Molecular Formula: C15H15FO3

Molecular Weight: 262.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H15FO3/c1-11(8-9-17)2-3-12-4-5-13(14(16)10-12)6-7-15(18)19/h4-5,8,10,17H,6-7,9H2,1H3,(H,18,19)/b11-8-

Standard InChI Key:  JVYDPNBFCZQRAE-FLIBITNWSA-N

Molfile:  

     RDKit          2D

 19 19  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
   -3.9005    5.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012    6.4541    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
    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
 14 15  1  0
  8 16  1  0
 16 17  2  0
  5 17  1  0
 17 18  1  0
  2 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3785413

   3-[2-fluoro-4-[(Z)-5-hydroxy-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: 262.28

Molecular Weight (Monoisotopic): 262.1005

AlogP: 2.13

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: -0.66

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: 0.18

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