3-ethyl 6-methyl 4-(3-acetylphenylamino)quinoline-3,6-dicarboxylate

ID: ALA213905

PubChem CID: 1187597

Max Phase: Preclinical

Molecular Formula: C22H20N2O5

Molecular Weight: 392.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2ccc(C(=O)OC)cc2c1Nc1cccc(C(C)=O)c1

Standard InChI:  InChI=1S/C22H20N2O5/c1-4-29-22(27)18-12-23-19-9-8-15(21(26)28-3)11-17(19)20(18)24-16-7-5-6-14(10-16)13(2)25/h5-12H,4H2,1-3H3,(H,23,24)

Standard InChI Key:  WKUCRZYWCJQVMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.5011   -7.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4999   -8.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2013   -8.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1995   -7.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9014   -7.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9022   -8.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6083   -8.8149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3099   -8.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3052   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6026   -7.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0092   -7.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7128   -7.5097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0042   -6.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5982   -6.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7930   -7.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7928   -6.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0920   -7.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8950   -5.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8962   -4.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1895   -4.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4897   -4.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4968   -5.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1998   -6.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4155   -7.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1191   -7.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3866   -7.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1843   -3.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9038   -3.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597   -3.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  1  0
  6  7  2  0
  1  2  1  0
  7  8  1  0
 15 16  2  0
 15 17  1  0
  1 15  1  0
  5  4  1  0
 14 18  1  0
  8  9  2  0
 18 19  2  0
  4  1  2  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 10  5  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  2  3  2  0
 12 24  1  0
  5  6  1  0
 24 25  1  0
 11 12  1  0
 17 26  1  0
 11 13  2  0
 20 27  1  0
  9 11  1  0
 27 28  2  0
  3  6  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA213905

   3-Ethyl 6-methyl 4-[(3-acetylphenyl)amino]quinoline-3,6-dicarboxylate

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: 392.41

Molecular Weight (Monoisotopic): 392.1372

AlogP: 4.14

#Rotatable Bonds: 6

Polar Surface Area: 94.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.20

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.06

References

1. Kim ND, Yoon J, Kim JH, Lee JT, Chon YS, Hwang MK, Ha I, Song WJ..  (2006)  Putative therapeutic agents for the learning and memory deficits of people with Down syndrome.,  16  (14): [PMID:16698266] [10.1016/j.bmcl.2006.04.042]

Source

Source(1):

• Scientific Literature