5-(1H-indol-3-yl)-1-((tetrahydrofuran-2-yl)methyl)-1H-benzotriazole

ID: ALA4873980

PubChem CID: 164627576

Max Phase: Preclinical

Molecular Formula: C19H18N4O

Molecular Weight: 318.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc2c(-c3ccc4nnn(CC5CCCO5)c4c3)c[nH]c2c1

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

Standard InChI Key:  KYTMIFWYXYDFJY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    2.3759  -19.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747  -20.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828  -20.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810  -18.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896  -19.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7944  -20.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744  -20.3087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518  -19.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667  -18.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8146  -18.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6148  -18.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103  -16.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660  -17.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147  -16.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599  -17.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6045  -16.9242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195  -16.1137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7224  -15.9442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3121  -17.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0199  -16.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7669  -17.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3139  -16.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9054  -15.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061  -16.1087    0.0000 O   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:

   

   ALA4873980

   ---

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: 3.76

#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: 0.34

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.98

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