5-Fluoro-3-((E)-2-pyridin-3-yl-vinyl)-1H-indole

ID: ALA168956

PubChem CID: 44381485

Max Phase: Preclinical

Molecular Formula: C15H11FN2

Molecular Weight: 238.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc2[nH]cc(/C=C/c3cccnc3)c2c1

Standard InChI:  InChI=1S/C15H11FN2/c16-13-5-6-15-14(8-13)12(10-18-15)4-3-11-2-1-7-17-9-11/h1-10,18H/b4-3+

Standard InChI Key:  WPABSLYILGSEFI-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    1.6292   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -2.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.6958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -0.8500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  2  0
  5  1  1  0
  6  3  1  0
  7  5  2  0
  8  3  2  0
  9 15  1  0
 10  6  2  0
 11  8  1  0
 12  7  1  0
 13 11  2  0
 14 11  1  0
 15 12  2  0
 16 18  1  0
 17 12  1  0
 18 17  2  0
  6  2  1  0
 13 10  1  0
  9 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA168956

   5-Fluoro-3-((E)-2-pyridin-3-yl-vinyl)-1H-indole

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: 238.26

Molecular Weight (Monoisotopic): 238.0906

AlogP: 3.87

#Rotatable Bonds: 2

Polar Surface Area: 28.68

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.88

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.72

Np Likeness Score: -0.90

References

1. Madge D, Hazelwood R, Iyer R, Jones H, Salter M.  (1996)  Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors,  6  (7): [10.1016/0960-894X(96)00124-2]

2. 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