N-(3-((1H-Indol-1-yl)methyl)benzyl)-4-bromo-1H-pyrrole-2-carboxamide

ID: ALA4482946

PubChem CID: 155539848

Max Phase: Preclinical

Molecular Formula: C21H18BrN3O

Molecular Weight: 408.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1cccc(Cn2ccc3ccccc32)c1)c1cc(Br)c[nH]1

Standard InChI:  InChI=1S/C21H18BrN3O/c22-18-11-19(23-13-18)21(26)24-12-15-4-3-5-16(10-15)14-25-9-8-17-6-1-2-7-20(17)25/h1-11,13,23H,12,14H2,(H,24,26)

Standard InChI Key:  WWFMXNRQSXPWTH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   32.3726   -1.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3714   -2.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0836   -3.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7974   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7945   -1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0818   -1.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6593   -3.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9519   -2.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8660   -1.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0627   -1.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1999   -3.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6519   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8516   -2.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5982   -3.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1471   -4.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9454   -3.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5099   -3.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2211   -2.8020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9335   -3.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9348   -4.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6447   -2.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3898   -3.1355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9396   -2.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5298   -1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7269   -1.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8629   -1.0686    0.0000 Br  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  2  0
 24 25  1  0
 25 21  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4482946

   ---

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: 408.30

Molecular Weight (Monoisotopic): 407.0633

AlogP: 4.71

#Rotatable Bonds: 5

Polar Surface Area: 49.82

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -1.36

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