5,7-dimethoxy-N-(4-morpholinophenyl)-4-oxo-1,4-dihydroquinoline-2-carboxamide

ID: ALA4218042

PubChem CID: 145967519

Max Phase: Preclinical

Molecular Formula: C22H23N3O5

Molecular Weight: 409.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(=O)cc(C(=O)Nc3ccc(N4CCOCC4)cc3)[nH]c2c1

Standard InChI:  InChI=1S/C22H23N3O5/c1-28-16-11-17-21(20(12-16)29-2)19(26)13-18(24-17)22(27)23-14-3-5-15(6-4-14)25-7-9-30-10-8-25/h3-6,11-13H,7-10H2,1-2H3,(H,23,27)(H,24,26)

Standard InChI Key:  DEFGQHFKNBWHHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.4915  -25.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4903  -26.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1984  -26.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1966  -24.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9052  -25.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9086  -26.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6170  -26.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3267  -26.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3233  -25.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6103  -24.8395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6192  -27.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7837  -24.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1989  -27.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4915  -27.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0761  -25.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0297  -24.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7387  -25.2448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0272  -24.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7412  -26.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0341  -26.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0363  -27.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7458  -27.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4545  -27.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4489  -26.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7510  -28.5066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0433  -28.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0449  -29.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7526  -30.1401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4603  -29.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4603  -28.9097    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
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  1 12  1  0
  3 13  1  0
 13 14  1  0
 12 15  1  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218042

   ---

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: 409.44

Molecular Weight (Monoisotopic): 409.1638

AlogP: 2.63

#Rotatable Bonds: 5

Polar Surface Area: 92.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: 1.02

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -0.92

References

1. Ling T, Lang W, Feng X, Das S, Maier J, Jeffries C, Shelat A, Rivas F..  (2018)  Novel vitexin-inspired scaffold against leukemia.,  146  [PMID:29407975] [10.1016/j.ejmech.2018.01.004]

Source

Source(1):

• Scientific Literature