rac-N,N-diethyl-5,10-dihydroindeno[1,2-b]indole-10-carboxamide

ID: ALA2377327

PubChem CID: 71579683

Max Phase: Preclinical

Molecular Formula: C20H20N2O

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)C1c2ccccc2-c2[nH]c3ccccc3c21

Standard InChI:  InChI=1S/C20H20N2O/c1-3-22(4-2)20(23)18-13-9-5-6-10-14(13)19-17(18)15-11-7-8-12-16(15)21-19/h5-12,18,21H,3-4H2,1-2H3

Standard InChI Key:  XTARLFSAXRGTDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   13.7175  -11.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7163  -12.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4244  -13.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4226  -11.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1312  -11.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1360  -12.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9160  -13.0406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9083  -11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3952  -12.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3837  -11.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1643  -11.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1708  -12.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8794  -12.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5820  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5715  -11.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8623  -10.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1228  -10.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6643   -9.6607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3220  -10.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4650   -9.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4049   -8.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9464   -8.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0065   -9.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  9 12  1  0
 11 10  1  0
 10  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 17 19  2  0
 10 17  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2377327

   N,N-diethyl-5,10-dihydroindeno[1,2-b]indole-10-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: 304.39

Molecular Weight (Monoisotopic): 304.1576

AlogP: 4.15

#Rotatable Bonds: 3

Polar Surface Area: 36.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -0.36

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]

Source

Source(1):

• Scientific Literature