3-[Biphenyl-4-ylmethyl-(2-thiophen-2-yl-ethyl)-amino]-3-(1H-imidazol-4-yl)-propionic acid

ID: ALA362028

PubChem CID: 44390114

Max Phase: Preclinical

Molecular Formula: C25H25N3O2S

Molecular Weight: 431.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(c1c[nH]cn1)N(CCc1cccs1)Cc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C25H25N3O2S/c29-25(30)15-24(23-16-26-18-27-23)28(13-12-22-7-4-14-31-22)17-19-8-10-21(11-9-19)20-5-2-1-3-6-20/h1-11,14,16,18,24H,12-13,15,17H2,(H,26,27)(H,29,30)

Standard InChI Key:  KPDHBCNLGPTZNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.6500   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833    0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -1.3167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8125   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -2.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  2  1  0
  6  5  1  0
  7 15  1  0
  8 11  1  0
  9  4  2  0
 10  7  1  0
 11  1  2  0
 12  3  1  0
 13  3  1  0
 14 21  2  0
 15 13  1  0
 16 10  1  0
 17  7  2  0
 18 17  1  0
 19  6  2  0
 20 14  1  0
 21 26  1  0
 22 25  2  0
 23 12  1  0
 24  6  1  0
 25 23  1  0
 26 23  2  0
 27 20  1  0
 28 20  2  0
 29 27  2  0
 30 28  1  0
 31 30  2  0
  9  8  1  0
 14 22  1  0
 16 18  2  0
 31 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA362028

   3-[Biphenyl-4-ylmethyl-(2-thiophen-2-yl-ethyl)-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: 431.56

Molecular Weight (Monoisotopic): 431.1667

AlogP: 5.40

#Rotatable Bonds: 10

Polar Surface Area: 69.22

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.34

CX Basic pKa: 8.00

CX LogP: 2.60

CX LogD: 2.51

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.02

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