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

ID: ALA3964804

PubChem CID: 134150976

Max Phase: Preclinical

Molecular Formula: C29H28N2O4

Molecular Weight: 468.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(OCCCCn3cncc3CC(=O)O)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C29H28N2O4/c1-34-23-14-12-21(13-15-23)29(26-10-4-2-8-24(26)25-9-3-5-11-27(25)29)35-17-7-6-16-31-20-30-19-22(31)18-28(32)33/h2-5,8-15,19-20H,6-7,16-18H2,1H3,(H,32,33)

Standard InChI Key:  XBECDTZDQSYKDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.8707  -19.3440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2834  -20.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6918  -19.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8789  -21.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6291  -20.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8340  -20.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2879  -20.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.9505  -20.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6943  -21.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2361  -21.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.6427  -18.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256  -18.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4148  -17.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5976  -17.9385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1211  -17.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3419  -17.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3355  -18.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1107  -18.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3796  -16.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376  -15.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0961  -15.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0369  -16.0487    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
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  3 16  2  0
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 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  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 27  1  0
 28 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3964804

   ---

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: 468.55

Molecular Weight (Monoisotopic): 468.2049

AlogP: 5.29

#Rotatable Bonds: 10

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: 3.84

CX Basic pKa: 6.35

CX LogP: 4.03

CX LogD: 2.95

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: -0.16

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