(Z)-3-(6-Fluoro-1H-indol-3-yl)-2-phenylacrylonitrile

ID: ALA1812549

PubChem CID: 53391946

Max Phase: Preclinical

Molecular Formula: C17H11FN2

Molecular Weight: 262.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1c[nH]c2cc(F)ccc12)c1ccccc1

Standard InChI:  InChI=1S/C17H11FN2/c18-15-6-7-16-14(11-20-17(16)9-15)8-13(10-19)12-4-2-1-3-5-12/h1-9,11,20H/b13-8+

Standard InChI Key:  LGADBOQXTUFTLP-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    1.8527    0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5664   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5646    0.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802   -0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0707   -0.9673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5590   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0703    0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250    1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319    1.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3866    2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -1.1226    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1926    2.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474    3.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    3.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0844    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    2.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6841    0.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    0.1086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  9 10  1  0
  5  6  1  0
 10 11  2  0
 11 12  1  0
  2  3  1  0
  2 13  1  0
  3  6  2  0
 12 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 12  1  0
  8  9  2  0
 11 19  1  0
  9  5  1  0
 19 20  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812549

   (Z)-3-(6-fluoro-1H-indol-3-yl)-2-phenylprop-2-enenitrile

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: 262.29

Molecular Weight (Monoisotopic): 262.0906

AlogP: 4.37

#Rotatable Bonds: 2

Polar Surface Area: 39.58

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.68

Np Likeness Score: -1.27

References

1. 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