(E)-Ethyl 2-cyano-3-(6-fluoro-1H-indol-3-yl)acrylate

ID: ALA1812550

PubChem CID: 53391947

Max Phase: Preclinical

Molecular Formula: C14H11FN2O2

Molecular Weight: 258.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H11FN2O2/c1-2-19-14(18)9(7-16)5-10-8-17-13-6-11(15)3-4-12(10)13/h3-6,8,17H,2H2,1H3/b9-5+

Standard InChI Key:  FEBZIDUDFVQQJL-WEVVVXLNSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    8.8986    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8974   -0.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6122   -0.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6104    0.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3258    0.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3261   -0.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1165   -0.6465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6049    0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1161    0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3708    1.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1777    1.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4324    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1826   -0.8018    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2393    2.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8802    3.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7915    1.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5985    2.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7299    1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2816    0.4294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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
  2 13  1  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 12 15  2  0
  5  4  2  0
 14 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 11 18  1  0
  8  9  2  0
 18 19  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812550

   ethyl (E)-2-cyano-3-(6-fluoro-1H-indol-3-yl)prop-2-enoate

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: 258.25

Molecular Weight (Monoisotopic): 258.0805

AlogP: 2.78

#Rotatable Bonds: 3

Polar Surface Area: 65.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.52

Np Likeness Score: -1.18

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