3-[[2-(4-Fluoro-phenyl)-ethyl]-(4-phenoxy-benzyl)-amino]-3-(1H-imidazol-4-yl)-propionic acid

ID: ALA426056

PubChem CID: 11363131

Max Phase: Preclinical

Molecular Formula: C27H26FN3O3

Molecular Weight: 459.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(c1c[nH]cn1)N(CCc1ccc(F)cc1)Cc1ccc(Oc2ccccc2)cc1

Standard InChI:  InChI=1S/C27H26FN3O3/c28-22-10-6-20(7-11-22)14-15-31(26(16-27(32)33)25-17-29-19-30-25)18-21-8-12-24(13-9-21)34-23-4-2-1-3-5-23/h1-13,17,19,26H,14-16,18H2,(H,29,30)(H,32,33)

Standard InChI Key:  FJGNOYWWYBUMAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -2.7125   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3500   -0.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208    0.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4208   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -2.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.9292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  2  1  0
  6  5  1  0
  7  9  1  0
  8  3  2  0
  9  1  2  0
 10  4  1  0
 11  4  1  0
 12  6  2  0
 13 15  1  0
 14 10  1  0
 15 24  1  0
 16 26  1  0
 17 19  1  0
 18  6  1  0
 19 11  1  0
 20 13  1  0
 21 16  1  0
 22 14  2  0
 23 14  1  0
 24 23  2  0
 25 22  1  0
 26 29  2  0
 27 28  1  0
 28 17  2  0
 29 17  1  0
 30 20  1  0
 31 20  2  0
 32 30  2  0
 33 31  1  0
 34 33  2  0
  8  7  1  0
 15 25  2  0
 16 27  2  0
 34 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA426056

   3-[[2-(4-Fluoro-phenyl)-ethyl]-(4-phenoxy-benzyl)-amino]-3-(1H-imidazol-4-yl)-propionic acid

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: 459.52

Molecular Weight (Monoisotopic): 459.1958

AlogP: 5.60

#Rotatable Bonds: 11

Polar Surface Area: 78.45

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.00

CX Basic pKa: 7.80

CX LogP: 2.68

CX LogD: 2.56

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -0.72

References

1. Saha AK, End DW..  (2005)  Novel beta-(imidazol-4-yl)-beta-amino acids: solid-phase synthesis and study of their inhibitory activity against geranylgeranyl protein transferase type I.,  15  (6): [PMID:15745827] [10.1016/j.bmcl.2005.01.042]

Source

Source(1):

• Scientific Literature