5-(1H-indol-3-yl)-1-methyl-4-nitro-1H-benzo[d][1,2,3]triazole

ID: ALA4863129

PubChem CID: 164624463

Max Phase: Preclinical

Molecular Formula: C14H9N5O2

Molecular Weight: 279.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1c(-c2c[nH]c3ccccc23)ccc2nn[nH]c12

Standard InChI:  InChI=1S/C14H9N5O2/c20-19(21)14-9(5-6-12-13(14)17-18-16-12)10-7-15-11-4-2-1-3-8(10)11/h1-7,15H,(H,16,17,18)

Standard InChI Key:  VTPSKTIVVWZZET-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    3.2343  -19.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332  -20.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412  -20.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394  -18.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481  -19.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529  -20.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329  -20.2798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102  -19.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251  -18.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6731  -18.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4732  -18.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3688  -16.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1245  -17.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732  -16.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184  -17.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4629  -16.8953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3779  -16.0848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5809  -15.9153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0260  -18.6128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8245  -18.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7772  -19.3912    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
 19 20  2  0
 19 21  1  0
 11 19  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4863129

   ---

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: 279.26

Molecular Weight (Monoisotopic): 279.0756

AlogP: 3.01

#Rotatable Bonds: 2

Polar Surface Area: 100.50

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.76

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: 1.65

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: -0.81

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