6-Fluoro-3-((E)-2-pyridin-4-yl-vinyl)-1H-indole

ID: ALA435072

Cas Number: 163239-23-4

PubChem CID: 10331757

Max Phase: Preclinical

Molecular Formula: C15H11FN2

Molecular Weight: 238.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc2c(/C=C/c3ccncc3)c[nH]c2c1

Standard InChI:  InChI=1S/C15H11FN2/c16-13-3-4-14-12(10-18-15(14)9-13)2-1-11-5-7-17-8-6-11/h1-10,18H/b2-1+

Standard InChI Key:  UJTBWNKRXRHIGU-OWOJBTEDSA-N

Molfile:  

     RDKit          2D

 18 20  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
   -0.2958   -2.1792    0.0000 C   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
   -0.2958   -1.3500    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
   -1.0083   -2.5917    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
    1.5542   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167    2.2208    0.0000 N   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
   -1.7208   -1.3500    0.0000 C   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
   -2.4375   -2.5875    0.0000 F   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
    2.8792    1.6083    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
    2.6250    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  2  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  2  2  0
  8  4  2  0
  9  6  2  0
 10 16  2  0
 11  7  1  0
 12 11  2  0
 13  9  1  0
 14 11  1  0
 15 17  2  0
 16 18  1  0
 17 13  1  0
 18 13  2  0
  3  4  1  0
  8 12  1  0
 15 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA435072

   6-Fluoro-3-((E)-2-pyridin-4-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: 238.26

Molecular Weight (Monoisotopic): 238.0906

AlogP: 3.87

#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: 5.28

CX LogP: 3.34

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.72

Np Likeness Score: -0.63

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]

Source

Source(1):

• Scientific Literature