3-((E)-2-Pyridin-3-yl-vinyl)-1H-indole

ID: ALA441669

PubChem CID: 14948489

Max Phase: Preclinical

Molecular Formula: C15H12N2

Molecular Weight: 220.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(=C/c1c[nH]c2ccccc12)\c1cccnc1

Standard InChI:  InChI=1S/C15H12N2/c1-2-6-15-14(5-1)13(11-17-15)8-7-12-4-3-9-16-10-12/h1-11,17H/b8-7+

Standard InChI Key:  XEGNKAULPJNZHP-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
    0.4917   -2.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    2.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  1  1  0
  7  4  2  0
  8 10  1  0
  9  7  1  0
 10  9  2  0
 11  5  2  0
 12 15  1  0
 13  6  2  0
 14  9  1  0
 15 14  2  0
 16 17  2  0
 17 13  1  0
  2  5  1  0
 11 16  1  0
  8 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA441669

   3-((E)-2-Pyridin-3-yl-vinyl)-1H-indole

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 220.28

Molecular Weight (Monoisotopic): 220.1000

AlogP: 3.73

#Rotatable Bonds: 2

Polar Surface Area: 28.68

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.88

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 3

Heavy Atoms: 17

QED Weighted: 0.70

Np Likeness Score: -0.35

References

1. Madge D, Hazelwood R, Iyer R, Jones H, Salter M.  (1996)  Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors,  6  (7): [10.1016/0960-894X(96)00124-2]

2. Dolusić E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frédérick R..  (2011)  Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.,  54  (15): [PMID:21726069] [10.1021/jm2006782]

3. Hua S, Chen F, Gou S..  (2020)  Microtubule inhibitors containing immunostimulatory agents promote cancer immunochemotherapy by inhibiting tubulin polymerization and tryptophan-2,3-dioxygenase.,  187  [PMID:31830637] [10.1016/j.ejmech.2019.111949]

Source

Source(1):

• Scientific Literature