(E)-2-Cyano-3-(6-fluoro-1H-indol-3-yl)acrylic acid

ID: ALA1812551

PubChem CID: 53392057

Max Phase: Preclinical

Molecular Formula: C12H7FN2O2

Molecular Weight: 230.20

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H7FN2O2/c13-9-1-2-10-8(6-15-11(10)4-9)3-7(5-14)12(16)17/h1-4,6,15H,(H,16,17)/b7-3+

Standard InChI Key:  JONAYMMCHYGONJ-XVNBXDOJSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   15.7277    0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7266   -0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4414   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4396    0.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1550    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552   -0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9457   -0.9673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4340   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9453    0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2000    1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0069    1.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2616    2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   -1.1226    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5591    0.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1172    0.1082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0685    2.2903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7093    2.7314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 11 14  1  0
  1  2  2  0
 14 15  3  0
  5  4  2  0
 12 16  1  0
  6  7  1  0
 12 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812551

   (E)-2-cyano-3-(6-fluoro-1H-indol-3-yl)prop-2-enoic 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: 230.20

Molecular Weight (Monoisotopic): 230.0492

AlogP: 2.30

#Rotatable Bonds: 2

Polar Surface Area: 76.88

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.32

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: -1.33

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.61

Np Likeness Score: -0.86

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