4-(2-(6-(1H-indol-3-yl)-1H-benzotriazol-1-yl)ethyl)morpholine

ID: ALA4870770

PubChem CID: 164621991

Max Phase: Preclinical

Molecular Formula: C20H21N5O

Molecular Weight: 347.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc2c(-c3ccc4c(c3)nnn4CCN3CCOCC3)c[nH]c2c1

Standard InChI:  InChI=1S/C20H21N5O/c1-2-4-18-16(3-1)17(14-21-18)15-5-6-20-19(13-15)22-23-25(20)8-7-24-9-11-26-12-10-24/h1-6,13-14,21H,7-12H2

Standard InChI Key:  GNMFEUSRBKSIAG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   11.2700   -6.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2689   -6.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9769   -7.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9752   -5.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6838   -6.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6886   -6.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4686   -7.2419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9460   -6.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4609   -5.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7088   -5.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5089   -4.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4045   -3.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1602   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2089   -3.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7541   -4.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4986   -3.8574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4136   -3.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6166   -2.8774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2843   -2.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7648   -1.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -0.7232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9205   -0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5915    0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7789    0.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2963    0.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6263   -0.6392    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  2  0
 17 18  1  0
 18 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870770

   ---

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: 347.42

Molecular Weight (Monoisotopic): 347.1746

AlogP: 2.91

#Rotatable Bonds: 4

Polar Surface Area: 58.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.82

CX LogP: 2.97

CX LogD: 2.87

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -1.59

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