(E)-3-(6-Fluoro-1H-indol-3-yl)acrylic acid

ID: ALA1812547

PubChem CID: 28806364

Max Phase: Preclinical

Molecular Formula: C11H8FNO2

Molecular Weight: 205.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C=C/c1c[nH]c2cc(F)ccc12

Standard InChI:  InChI=1S/C11H8FNO2/c12-8-2-3-9-7(1-4-11(14)15)6-13-10(9)5-8/h1-6,13H,(H,14,15)/b4-1+

Standard InChI Key:  ZJQAEZVFMQFBPD-DAFODLJHSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   17.9194  -25.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9182  -26.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6331  -26.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6313  -25.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3466  -25.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3469  -26.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1374  -26.5590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6257  -25.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1369  -25.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3916  -24.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1985  -24.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4532  -23.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2601  -23.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9010  -22.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2035  -26.7143    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  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
 12 13  1  0
  3  6  2  0
 12 14  2  0
  1  2  2  0
  2 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812547

   (E)-3-(6-Fluoro-1H-indol-3-YL)acrylic acid

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: 205.19

Molecular Weight (Monoisotopic): 205.0539

AlogP: 2.40

#Rotatable Bonds: 2

Polar Surface Area: 53.09

Molecular Species: ACID

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: ┄

CX LogP: 2.38

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.74

Np Likeness Score: -0.26

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