3-(1-{5-[9-(4-Methoxyphenyl)-9H-fluoren-9-yloxy]pentyl}-1H-imidazol-2-yl)prop-2-enoic acid

ID: ALA3918088

PubChem CID: 134142899

Max Phase: Preclinical

Molecular Formula: C31H30N2O4

Molecular Weight: 494.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(OCCCCCn3ccnc3/C=C/C(=O)O)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C31H30N2O4/c1-36-24-15-13-23(14-16-24)31(27-11-5-3-9-25(27)26-10-4-6-12-28(26)31)37-22-8-2-7-20-33-21-19-32-29(33)17-18-30(34)35/h3-6,9-19,21H,2,7-8,20,22H2,1H3,(H,34,35)/b18-17+

Standard InChI Key:  RQUBNQISVIUDBQ-ISLYRVAYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   36.0952  -18.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6866  -19.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4399  -18.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6477  -18.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1013  -19.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3526  -20.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1443  -20.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7581  -18.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5029  -19.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0470  -20.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8465  -20.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0990  -19.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5532  -18.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5107  -17.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6704  -17.8049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4614  -18.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0347  -17.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8171  -16.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3904  -16.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1727  -15.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7460  -14.6878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5505  -14.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9158  -14.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3335  -13.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6083  -13.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9288  -15.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7452  -15.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1234  -16.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9399  -16.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6852  -16.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7274  -17.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1437  -16.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3445  -16.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1322  -17.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7174  -18.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7658  -16.0590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9762  -15.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  8  1  1  0
  1  3  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
 22 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 14 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 14  1  0
 33 36  1  0
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3918088

   ---

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: 494.59

Molecular Weight (Monoisotopic): 494.2206

AlogP: 6.15

#Rotatable Bonds: 11

Polar Surface Area: 73.58

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.79

CX Basic pKa: 6.15

CX LogP: 4.85

CX LogD: 3.63

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: -0.07

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