N-(3-((1H-Benzo[d]imidazol-1-yl)methyl)benzyl)-4-aminobutanamide

ID: ALA4534569

PubChem CID: 119862887

Max Phase: Preclinical

Molecular Formula: C19H22N4O

Molecular Weight: 322.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCCCC(=O)NCc1cccc(Cn2cnc3ccccc32)c1

Standard InChI:  InChI=1S/C19H22N4O/c20-10-4-9-19(24)21-12-15-5-3-6-16(11-15)13-23-14-22-17-7-1-2-8-18(17)23/h1-3,5-8,11,14H,4,9-10,12-13,20H2,(H,21,24)

Standard InChI Key:  RJYJZYNLEAWCNF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   32.2859  -20.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2847  -21.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9969  -21.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7107  -21.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7079  -20.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9951  -19.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5726  -21.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8652  -21.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7793  -20.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9760  -20.0936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1132  -21.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5652  -20.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7649  -20.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5115  -21.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0604  -22.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8587  -22.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4232  -21.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1344  -21.0774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8469  -21.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8481  -22.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5580  -21.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2654  -21.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9735  -21.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6808  -21.4858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 12  1  0
 11  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534569

   ---

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: 322.41

Molecular Weight (Monoisotopic): 322.1794

AlogP: 2.44

#Rotatable Bonds: 7

Polar Surface Area: 72.94

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.99

CX LogP: 1.75

CX LogD: -0.71

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -1.40

References

1. Serafini M, Torre E, Aprile S, Grosso ED, Gesù A, Griglio A, Colombo G, Travelli C, Paiella S, Adamo A, Orecchini E, Coletti A, Pallotta MT, Ugel S, Massarotti A, Pirali T, Fallarini S..  (2020)  Discovery of Highly Potent Benzimidazole Derivatives as Indoleamine 2,3-Dioxygenase-1 (IDO1) Inhibitors: From Structure-Based Virtual Screening to in Vivo Pharmacodynamic Activity.,  63  (6): [PMID:32150677] [10.1021/acs.jmedchem.9b01809]

Source

Source(1):

• Scientific Literature