(S)-3-(4-(2-(3-chlorophenoxy)ethoxy)phenyl)hex-4-ynoic acid

ID: ALA3927863

PubChem CID: 134140733

Max Phase: Preclinical

Molecular Formula: C20H19ClO4

Molecular Weight: 358.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@@H](CC(=O)O)c1ccc(OCCOc2cccc(Cl)c2)cc1

Standard InChI:  InChI=1S/C20H19ClO4/c1-2-4-16(13-20(22)23)15-7-9-18(10-8-15)24-11-12-25-19-6-3-5-17(21)14-19/h3,5-10,14,16H,11-13H2,1H3,(H,22,23)/t16-/m0/s1

Standard InChI Key:  LBEBVHDEHJNPCA-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   22.8619  -13.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5712  -13.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2773  -13.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9850  -13.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6907  -13.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6880  -12.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738  -11.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2711  -12.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3937  -11.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1034  -12.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3895  -11.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3812  -10.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3771   -9.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8091  -11.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5188  -12.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8049  -11.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1558  -13.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4465  -13.1773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7404  -13.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0335  -13.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3279  -13.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3305  -14.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0447  -14.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7475  -14.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6188  -13.1839    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  3  0
 12 13  1  0
 10 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3927863

   ---

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: 358.82

Molecular Weight (Monoisotopic): 358.0972

AlogP: 4.38

#Rotatable Bonds: 8

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -0.45

References

1. Chen C, Li H, Long YQ..  (2016)  GPR40 agonists for the treatment of type 2 diabetes mellitus: The biological characteristics and the chemical space.,  26  (23): [PMID:27825762] [10.1016/j.bmcl.2016.10.074]

Source

Source(1):

• Scientific Literature