Prop-2-yn-1-yl-2-Amino-6-(2-methoxypyridin-4-yl)-4-(2-oxo-2-(prop-2-yn-1-yloxy)ethyl)-4H-chromene-3-carboxylate

ID: ALA4174955

PubChem CID: 145950649

Max Phase: Preclinical

Molecular Formula: C24H20N2O6

Molecular Weight: 432.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3ccnc(OC)c3)cc21

Standard InChI:  InChI=1S/C24H20N2O6/c1-4-10-30-21(27)14-18-17-12-15(16-8-9-26-20(13-16)29-3)6-7-19(17)32-23(25)22(18)24(28)31-11-5-2/h1-2,6-9,12-13,18H,10-11,14,25H2,3H3

Standard InChI Key:  GXOVZOFPQWLNTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   27.0025  -19.7457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0014  -20.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7163  -20.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4326  -20.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4298  -19.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7145  -19.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1478  -20.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1442  -21.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8584  -22.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8545  -20.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5693  -20.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5704  -21.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2824  -22.2136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9979  -21.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9969  -20.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2802  -20.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7123  -22.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7111  -20.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4258  -20.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7109  -19.7380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1401  -20.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1398  -19.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1395  -18.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2780  -19.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5624  -19.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5602  -18.5008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8490  -19.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2735  -18.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9891  -18.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7047  -18.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2866  -20.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5725  -20.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
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 15 16  1  0
 14 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  3  0
 16 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  3  0
  2 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174955

   ---

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: 432.43

Molecular Weight (Monoisotopic): 432.1321

AlogP: 2.15

#Rotatable Bonds: 7

Polar Surface Area: 109.97

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.07

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -0.56

References

1. Bian T, Chandagirikoppal Vijendra K, Wang Y, Meacham A, Hati S, Cogle CR, Sun H, Xing C..  (2018)  Exploring the Structure-Activity Relationship and Mechanism of a Chromene Scaffold (CXL Series) for Its Selective Antiproliferative Activity toward Multidrug-Resistant Cancer Cells.,  61  (15): [PMID:29995404] [10.1021/acs.jmedchem.8b00813]

Source

Source(1):

• Scientific Literature