Ethyl 4-(2,3-dichlorophenyl)-2,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

ID: ALA521863

PubChem CID: 24851442

Max Phase: Preclinical

Molecular Formula: C20H21Cl2NO3

Molecular Weight: 394.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC2=C(C(=O)CC(C)C2)C1c1cccc(Cl)c1Cl

Standard InChI:  InChI=1S/C20H21Cl2NO3/c1-4-26-20(25)16-11(3)23-14-8-10(2)9-15(24)18(14)17(16)12-6-5-7-13(21)19(12)22/h5-7,10,17,23H,4,8-9H2,1-3H3

Standard InChI Key:  FREUMSVVYXYLQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    0.3450   -0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450   -1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595   -1.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595    0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739   -0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739   -1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884   -1.5318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0595    0.9432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    0.9432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318   -0.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739    1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739    2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    2.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029    2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029    1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    1.4420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695   -1.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318    1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3463    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    2.5932    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
 12 13  1  0
 12 14  2  0
  9 12  1  0
  2  3  1  0
  8 15  1  0
  3  6  1  0
 10 16  1  0
  5  4  1  0
 16 17  2  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  2  0
 20 21  2  0
 21 16  1  0
  9 10  1  0
 21 22  1  0
  5  6  2  0
  2 23  1  0
  4 11  2  0
 13 24  1  0
 24 25  1  0
  1  2  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA521863

   ethyl 4-(2,3-dichlorophenyl)-2,7-dimethyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate

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: 394.30

Molecular Weight (Monoisotopic): 393.0898

AlogP: 4.77

#Rotatable Bonds: 3

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -0.93

References

1. Gündüz MG, Sevim Oztürk G, Vural IM, Simşek R, Sarioğlu Y, Safak C..  (2008)  Evaluation of myorelaxant activity of 7-substituted hexahydroquinoline derivatives in isolated rabbit gastric fundus.,  43  (3): [PMID:17590241] [10.1016/j.ejmech.2007.04.012]

Source

Source(1):

• Scientific Literature