5-(1H-indol-3-yl)-1-((tetrahydrofuran-3-yl)methyl)-1H-benzo[d][1,2,3]triazole

ID: ALA4871428

PubChem CID: 164621160

Max Phase: Preclinical

Molecular Formula: C19H18N4O

Molecular Weight: 318.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc2c(-c3ccc4nnn(CC5CCOC5)c4c3)c[nH]c2c1

Standard InChI:  InChI=1S/C19H18N4O/c1-2-4-17-15(3-1)16(10-20-17)14-5-6-18-19(9-14)23(22-21-18)11-13-7-8-24-12-13/h1-6,9-10,13,20H,7-8,11-12H2

Standard InChI Key:  VUWSQISNVLCMTI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    2.6235   -4.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6224   -5.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -6.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286   -4.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372   -4.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420   -5.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221   -6.0161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994   -5.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8143   -4.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -3.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8624   -3.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -2.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136   -3.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1075   -2.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8521   -2.6316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7671   -1.8211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9700   -1.6516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5597   -3.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2675   -2.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0127   -2.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5597   -2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1512   -1.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3519   -1.8202    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
  9 10  1  0
 10 11  2  0
 11 15  1  0
 14 12  1  0
 12 13  2  0
 13 10  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871428

   ---

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: 318.38

Molecular Weight (Monoisotopic): 318.1481

AlogP: 3.62

#Rotatable Bonds: 3

Polar Surface Area: 55.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.36

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.94

References

1. Kozlova A, Thabault L, Liberelle M, Klaessens S, Prévost JRC, Mathieu C, Pilotte L, Stroobant V, Van den Eynde B, Frédérick R..  (2021)  Rational Design of Original Fused-Cycle Selective Inhibitors of Tryptophan 2,3-Dioxygenase.,  64  (15.0): [PMID:34338527] [10.1021/acs.jmedchem.1c00323]

Source

Source(1):

• Scientific Literature