2-((6-Fluoro-1H-indol-3-yl)methylene)malonic acid

ID: ALA1812552

PubChem CID: 53392058

Max Phase: Preclinical

Molecular Formula: C12H8FNO4

Molecular Weight: 249.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(=Cc1c[nH]c2cc(F)ccc12)C(=O)O

Standard InChI:  InChI=1S/C12H8FNO4/c13-7-1-2-8-6(5-14-10(8)4-7)3-9(11(15)16)12(17)18/h1-5,14H,(H,15,16)(H,17,18)

Standard InChI Key:  YABYWBVLDCDXDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   22.4069    0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4057   -0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1206   -0.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1187    0.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8341    0.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8344   -0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6249   -0.8423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1132   -0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6244    0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8791    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6860    1.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9407    2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6910   -0.9976    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.7476    2.4153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3885    2.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2383    0.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9836    0.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0452    1.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 11 16  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812552

   2-[(6-fluoro-1H-indol-3-yl)methylidene]propanedioic 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: 249.20

Molecular Weight (Monoisotopic): 249.0437

AlogP: 1.86

#Rotatable Bonds: 3

Polar Surface Area: 90.39

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.72

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: -4.77

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.44

Np Likeness Score: -0.49

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