3-(6-(1H-indol-3-yl)-1H-benzo[d][1,2,3]triazol-1-yl)propane-1,2-diol

ID: ALA4870875

PubChem CID: 164619827

Max Phase: Preclinical

Molecular Formula: C17H16N4O2

Molecular Weight: 308.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OCC(O)Cn1nnc2cc(-c3c[nH]c4ccccc34)ccc21

Standard InChI:  InChI=1S/C17H16N4O2/c22-10-12(23)9-21-17-6-5-11(7-16(17)19-20-21)14-8-18-15-4-2-1-3-13(14)15/h1-8,12,18,22-23H,9-10H2

Standard InChI Key:  CZHIWENXJPDIOV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   30.5731  -21.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5719  -21.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2800  -22.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2782  -20.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9868  -21.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9916  -21.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7717  -22.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2490  -21.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7639  -20.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0119  -19.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8120  -19.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7075  -18.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4632  -19.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5120  -18.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0571  -19.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8017  -18.7113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7167  -17.9008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9196  -17.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5874  -16.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0678  -16.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7356  -15.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2160  -14.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8805  -16.4092    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  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
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870875

   ---

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: 308.34

Molecular Weight (Monoisotopic): 308.1273

AlogP: 1.93

#Rotatable Bonds: 4

Polar Surface Area: 86.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 0.30

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.92

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