(1-{(1E)-3-[9-(4-Methoxyphenyl)-9H-fluoren-9-yl]prop-2-en-1-yl}-1H-imidazol-5-yl)acetic acid

ID: ALA3900013

PubChem CID: 134134192

Max Phase: Preclinical

Molecular Formula: C28H24N2O3

Molecular Weight: 436.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(C/C=C/n3cncc3CC(=O)O)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C28H24N2O3/c1-33-22-13-11-20(12-14-22)28(15-6-16-30-19-29-18-21(30)17-27(31)32)25-9-4-2-7-23(25)24-8-3-5-10-26(24)28/h2-14,16,18-19H,15,17H2,1H3,(H,31,32)/b16-6+

Standard InChI Key:  YDUOZLHUJXRQQL-OMCISZLKSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   35.2878   -4.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7005   -4.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1089   -4.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2960   -6.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0462   -5.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2512   -5.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7051   -5.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9596   -6.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7541   -6.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3676   -5.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1114   -6.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6533   -6.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4514   -6.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7048   -5.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1612   -5.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9295   -4.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3379   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9251   -2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0997   -2.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6951   -3.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3306   -2.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1478   -2.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4706   -4.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0599   -3.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2427   -3.5041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7589   -2.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9825   -3.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9849   -3.9148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7629   -4.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0090   -2.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8078   -1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0579   -1.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3565   -2.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 11  1  0
 10  2  1  0
  2  5  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 18 21  1  0
 21 22  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
 26 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3900013

   ---

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: 436.51

Molecular Weight (Monoisotopic): 436.1787

AlogP: 5.39

#Rotatable Bonds: 7

Polar Surface Area: 64.35

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.85

CX Basic pKa: 5.98

CX LogP: 4.10

CX LogD: 2.71

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: 0.03

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