9-amino-N-(3-chlorophenyl)-2,3-dihydro-[1,4]dioxino[2,3-g]thieno[2,3-b]quinoline-8-carboxamide

ID: ALA3261354

PubChem CID: 86763877

Max Phase: Preclinical

Molecular Formula: C20H14ClN3O3S

Molecular Weight: 411.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(C(=O)Nc2cccc(Cl)c2)sc2nc3cc4c(cc3cc12)OCCO4

Standard InChI:  InChI=1S/C20H14ClN3O3S/c21-11-2-1-3-12(8-11)23-19(25)18-17(22)13-6-10-7-15-16(27-5-4-26-15)9-14(10)24-20(13)28-18/h1-3,6-9H,4-5,22H2,(H,23,25)

Standard InChI Key:  APEJMMAQPWUEPN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   15.8563  -21.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8563  -19.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5616  -20.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5581  -21.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2602  -21.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2671  -19.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9737  -20.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9677  -21.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7427  -21.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2277  -20.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7524  -20.0529    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.0449  -20.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4483  -21.4339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4587  -20.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2655  -21.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6638  -22.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4802  -22.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8948  -21.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4870  -20.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6719  -20.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1511  -21.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1466  -20.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4406  -19.8912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7345  -20.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7391  -21.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4496  -21.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9895  -22.1536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8833  -22.8684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 22  2  2  0
 21  1  2  0
  1  4  1  0
  3  2  1  0
  3  4  1  0
  3  6  2  0
  4  5  2  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  9 27  1  0
 17 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3261354

   15-amino-N-(3-chlorophenyl)-4,7-dioxa-13-thia-11-azatetracyclo[8.7.0.03,8.012,16]heptadeca-1(17),2,8,10,12(16),14-hexaene-14-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: 411.87

Molecular Weight (Monoisotopic): 411.0444

AlogP: 4.71

#Rotatable Bonds: 2

Polar Surface Area: 86.47

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.42

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.95

References

1. Rechfeld F, Gruber P, Kirchmair J, Boehler M, Hauser N, Hechenberger G, Garczarczyk D, Lapa GB, Preobrazhenskaya MN, Goekjian P, Langer T, Hofmann J..  (2014)  Thienoquinolines as novel disruptors of the PKCε/RACK2 protein-protein interaction.,  57  (8): [PMID:24712764] [10.1021/jm401605c]

Source

Source(1):

• Scientific Literature