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

ID: ALA1812546

PubChem CID: 53391943

Max Phase: Preclinical

Molecular Formula: C12H10FNO2

Molecular Weight: 219.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H10FNO2/c1-16-12(15)5-2-8-7-14-11-6-9(13)3-4-10(8)11/h2-7,14H,1H3/b5-2+

Standard InChI Key:  CKXVPLTXKONPSQ-GORDUTHDSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    2.7861  -25.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849  -26.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997  -26.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979  -25.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133  -25.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136  -26.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0040  -26.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4924  -26.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036  -25.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583  -24.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0652  -24.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3199  -23.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701  -26.8726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1268  -23.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677  -23.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6790  -24.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA1812546

   methyl (E)-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: 219.22

Molecular Weight (Monoisotopic): 219.0696

AlogP: 2.49

#Rotatable Bonds: 2

Polar Surface Area: 42.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.62

Np Likeness Score: -0.22

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