3-(1-(3-oxo-3-(m-tolylamino)propyl)-1H-benzo[d]imidazol-2-yl)propanoic acid

ID: ALA4513631

PubChem CID: 155538914

Max Phase: Preclinical

Molecular Formula: C20H21N3O3

Molecular Weight: 351.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(NC(=O)CCn2c(CCC(=O)O)nc3ccccc32)c1

Standard InChI:  InChI=1S/C20H21N3O3/c1-14-5-4-6-15(13-14)21-19(24)11-12-23-17-8-3-2-7-16(17)22-18(23)9-10-20(25)26/h2-8,13H,9-12H2,1H3,(H,21,24)(H,25,26)

Standard InChI Key:  FNESXDGXWWRKPL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.3164   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3153   -3.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0233   -3.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0215   -2.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7302   -2.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7350   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5150   -3.7131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9923   -3.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5072   -2.3886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5094   -4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2143   -4.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2087   -5.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8095   -3.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4982   -6.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9136   -6.1716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2139   -2.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0311   -2.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4355   -1.6181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4439   -3.0335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6241   -5.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3259   -6.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0359   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0419   -4.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3321   -4.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6250   -4.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7406   -6.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  1  0
 12 14  2  0
 12 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513631

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.41

Molecular Weight (Monoisotopic): 351.1583

AlogP: 3.39

#Rotatable Bonds: 7

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: 5.27

CX LogP: 1.95

CX LogD: 0.15

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: -1.86

References

1. Ma T, Huang M, Li A, Zhao F, Li D, Liu D, Zhao L..  (2019)  Design, synthesis and biological evaluation of benzimidazole derivatives as novel human Pin1 inhibitors.,  29  (14): [PMID:31103446] [10.1016/j.bmcl.2018.11.045]

Source

Source(1):

• Scientific Literature