(1-{3-[9-(4-Methoxyphenyl)-9H-fluoren-9-yloxy]propyl}-1H-imidazol-5-yl)acetic acid

ID: ALA3926947

PubChem CID: 134141790

Max Phase: Preclinical

Molecular Formula: C28H26N2O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(OCCCn3cncc3CC(=O)O)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C28H26N2O4/c1-33-22-13-11-20(12-14-22)28(34-16-6-15-30-19-29-18-21(30)17-27(31)32)25-9-4-2-7-23(25)24-8-3-5-10-26(24)28/h2-5,7-14,18-19H,6,15-17H2,1H3,(H,31,32)

Standard InChI Key:  WXEWOUGXNHWRBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   11.7668   -3.3649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0193   -2.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3578   -2.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6970   -2.5864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9503   -3.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7963   -2.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2224   -4.7711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6352   -5.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0436   -4.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2307   -6.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9809   -5.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1858   -5.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6397   -6.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8942   -7.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6887   -7.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3022   -5.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0460   -6.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5879   -7.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3860   -7.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6394   -6.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0959   -5.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8641   -4.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2725   -4.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8597   -3.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0343   -3.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6297   -4.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2652   -2.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0824   -2.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4052   -4.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9945   -4.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1773   -4.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9654   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7424   -1.2793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3576   -0.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  8  7  1  0
  9  8  1  0
 10 17  1  0
 16  8  1  0
  8 11  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
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  9  1  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 30 31  1  0
 31  1  1  0
  6 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3926947

   ---

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: 454.53

Molecular Weight (Monoisotopic): 454.1893

AlogP: 4.90

#Rotatable Bonds: 9

Polar Surface Area: 73.58

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: 6.34

CX LogP: 3.50

CX LogD: 2.42

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -0.19

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