3-[1-(4,4-Diphenylbut-3-en-1-yl)-1H-imidazol-2-yl]propanoic acid

ID: ALA3895253

PubChem CID: 134137068

Max Phase: Preclinical

Molecular Formula: C22H22N2O2

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1nccn1CCC=C(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C22H22N2O2/c25-22(26)14-13-21-23-15-17-24(21)16-7-12-20(18-8-3-1-4-9-18)19-10-5-2-6-11-19/h1-6,8-12,15,17H,7,13-14,16H2,(H,25,26)

Standard InChI Key:  WSJGZFXBIMCADT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.2644   -2.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240   -2.9928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -2.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -1.7355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -1.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3639   -2.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9736   -2.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7497   -2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3594   -1.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9160   -3.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206   -3.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266   -4.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6231   -5.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3256   -6.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -5.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -5.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4508   -5.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4547   -4.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -3.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378   -4.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -6.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6126   -7.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -7.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0309   -7.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -6.6746    0.0000 C   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  1  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 15 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3895253

   ---

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: 346.43

Molecular Weight (Monoisotopic): 346.1681

AlogP: 4.42

#Rotatable Bonds: 8

Polar Surface Area: 55.12

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.10

CX Basic pKa: 6.13

CX LogP: 2.85

CX LogD: 1.60

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -0.37

References

1. Kerscher-Hack S, Renukappa-Gutke T, Höfner G, Wanner KT..  (2016)  Synthesis and biological evaluation of a series of N-alkylated imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.,  124  [PMID:27654218] [10.1016/j.ejmech.2016.09.012]

Source

Source(1):

• Scientific Literature