rac-N,N-diethyl-11-(2-fluoroethyl)-7-methoxy-6,11-dihydrothiochromeno[4,3-b]indole-6-carboxamide

ID: ALA2377354

PubChem CID: 58382976

Max Phase: Preclinical

Molecular Formula: C23H25FN2O2S

Molecular Weight: 412.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)C1Sc2ccccc2-c2c1c1c(OC)cccc1n2CCF

Standard InChI:  InChI=1S/C23H25FN2O2S/c1-4-25(5-2)23(27)22-20-19-16(10-8-11-17(19)28-3)26(14-13-24)21(20)15-9-6-7-12-18(15)29-22/h6-12,22H,4-5,13-14H2,1-3H3

Standard InChI Key:  VWCQIIUQPHDCEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.2387   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    0.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385    1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -4.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -4.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673   -4.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -5.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -5.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -4.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781   -1.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396   -0.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5128    0.2422    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 18  1  0
 25 26  1  0
 26 16  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2377354

   N,N-diethyl-11-(2-fluoroethyl)-7-methoxy-6H-thiochromeno[4,3-b]indole-6-carboxamide

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: 412.53

Molecular Weight (Monoisotopic): 412.1621

AlogP: 5.30

#Rotatable Bonds: 6

Polar Surface Area: 34.47

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -0.82

References

1. O'Shea D, Ahmad R, Årstad E, Avory M, Chau WF, Durrant C, Hirani E, Jones PA, Khan I, Luthra SK, Mantzilas D, Morisson-Iveson V, Passmore J, Robins EG, Shan B, Wadsworth H, Walton S, Zhao Y, Trigg W..  (2013)  Exploration of the structure-activity relationship of a novel tetracyclic class of TSPO ligands-potential novel positron emitting tomography imaging agents.,  23  (8): [PMID:23489633] [10.1016/j.bmcl.2013.02.057]

2.  (2016)  Imaging neuroinflammation, 

Source

Source(2):

• Scientific Literature
• BindingDB Database