3-(4-(Phenylethynyl)phenyl)propanoic acid

ID: ALA488384

PubChem CID: 25149901

Max Phase: Preclinical

Molecular Formula: C17H14O2

Molecular Weight: 250.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-(4-(Phenylethynyl)Phenyl)Propanoic Acid | CHEMBL488384|3-(4-(Phenylethynyl)phenyl)propanoic acid|SCHEMBL1551253|BDBM50275510

Canonical SMILES:  O=C(O)CCc1ccc(C#Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C17H14O2/c18-17(19)13-12-16-10-8-15(9-11-16)7-6-14-4-2-1-3-5-14/h1-5,8-11H,12-13H2,(H,18,19)

Standard InChI Key:  ZOWBFTGCXGCEGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.3804  -15.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791  -16.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921  -17.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115  -16.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8084  -15.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0902  -15.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5208  -15.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2284  -14.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9389  -14.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6550  -14.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3648  -14.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3593  -13.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6379  -13.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9308  -13.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0703  -13.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7883  -13.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4993  -13.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2173  -13.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4922  -12.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
 14  9  1  0
  5  7  1  0
 12 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  3  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA488384

   3-(4-(Phenylethynyl)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: 250.30

Molecular Weight (Monoisotopic): 250.0994

AlogP: 3.10

#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: 3.90

CX Basic pKa: ┄

CX LogP: 4.18

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.85

Np Likeness Score: -0.26

References

1. Christiansen E, Urban C, Merten N, Liebscher K, Karlsen KK, Hamacher A, Spinrath A, Bond AD, Drewke C, Ullrich S, Kassack MU, Kostenis E, Ulven T..  (2008)  Discovery of potent and selective agonists for the free fatty acid receptor 1 (FFA(1)/GPR40), a potential target for the treatment of type II diabetes.,  51  (22): [PMID:18947221] [10.1021/jm8010178]

2. Christiansen E, Due-Hansen ME, Urban C, Merten N, Pfleiderer M, Karlsen KK, Rasmussen SS, Steensgaard M, Hamacher A, Schmidt J, Drewke C, Petersen RK, Kristiansen K, Ullrich S, Kostenis E, Kassack MU, Ulven T..  (2010)  Structure-Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469.,  1  (7): [PMID:24900217] [10.1021/ml100106c]

3. Christiansen E, Urban C, Grundmann M, Due-Hansen ME, Hagesaether E, Schmidt J, Pardo L, Ullrich S, Kostenis E, Kassack M, Ulven T..  (2011)  Identification of a potent and selective free fatty acid receptor 1 (FFA1/GPR40) agonist with favorable physicochemical and in vitro ADME properties.,  54  (19): [PMID:21854074] [10.1021/jm2005699]

4. Christiansen E, Hansen SV, Urban C, Hudson BD, Wargent ET, Grundmann M, Jenkins L, Zaibi M, Stocker CJ, Ullrich S, Kostenis E, Kassack MU, Milligan G, Cawthorne MA, Ulven T..  (2013)  Discovery of TUG-770: A Highly Potent Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist for Treatment of Type 2 Diabetes.,  4  (5): [PMID:23687558] [10.1021/ml4000673]

5. 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