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

ID: ALA3982271

PubChem CID: 134157063

Max Phase: Preclinical

Molecular Formula: C28H26N2O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(OCCCn3cnc(CC(=O)O)c3)c3ccccc3-c3ccccc32)cc1

Standard InChI:  InChI=1S/C28H26N2O4/c1-33-22-13-11-20(12-14-22)28(34-16-6-15-30-18-21(29-19-30)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:  MBYWTWATGDSTPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   14.3464  -11.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7591  -11.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1676  -11.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3546  -13.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1048  -12.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3098  -12.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7637  -12.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0182  -13.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8127  -13.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4262  -12.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1700  -13.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7119  -13.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5100  -13.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7634  -12.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2199  -12.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9881  -11.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3965  -10.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3892   -8.9264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2064   -8.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5292  -11.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1185  -10.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3013  -10.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8906   -9.6526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1564   -8.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5033   -8.3864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8343   -8.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0742   -9.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0613   -8.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9045   -7.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1317   -7.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5206   -7.2518    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  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982271

   ---

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: 3.59

CX Basic pKa: 6.17

CX LogP: 3.52

CX LogD: 2.32

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -0.12

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