6-(3-Adamantan-1-yl-ureido)-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

ID: ALA4207513

PubChem CID: 145978621

Max Phase: Preclinical

Molecular Formula: C22H25N3O4

Molecular Weight: 395.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(=O)c2cc(NC(=O)NC34CC5CC(CC(C5)C3)C4)ccc2[nH]1

Standard InChI:  InChI=1S/C22H25N3O4/c1-29-20(27)18-8-19(26)16-7-15(2-3-17(16)24-18)23-21(28)25-22-9-12-4-13(10-22)6-14(5-12)11-22/h2-3,7-8,12-14H,4-6,9-11H2,1H3,(H,24,26)(H2,23,25,28)

Standard InChI Key:  GCJOAIWENCAGKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   36.6321  -11.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2673  -10.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4331  -11.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9761  -11.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1828  -11.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7210  -10.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4305  -10.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9818   -9.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2629   -9.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7267  -10.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1070   -7.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1058   -8.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8139   -8.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8121   -7.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5207   -7.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5241   -8.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2325   -8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9422   -8.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9388   -7.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2258   -7.2493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2348   -9.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6452   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6427   -6.4310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3542   -7.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3567   -8.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3978   -8.8959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6904   -8.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6911   -7.6696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9824   -8.8948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 11 12  2  0
 12 13  1  0
 13 16  2  0
 15 14  2  0
 14 11  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 17 21  2  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 12 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4207513

   ---

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: 395.46

Molecular Weight (Monoisotopic): 395.1845

AlogP: 3.41

#Rotatable Bonds: 3

Polar Surface Area: 100.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -0.94

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