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

ID: ALA4171937

PubChem CID: 145952019

Max Phase: Preclinical

Molecular Formula: C23H18N2O6

Molecular Weight: 418.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H18N2O6/c1-3-9-29-20(27)13-17-16-11-14(15-7-8-25-19(26)12-15)5-6-18(16)31-22(24)21(17)23(28)30-10-4-2/h1-2,5-8,11-12,17H,9-10,13,24H2,(H,25,26)

Standard InChI Key:  GAIKHGSQQPDOMN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   27.3108   -4.8915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3096   -5.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0245   -6.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7408   -5.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7380   -4.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0226   -4.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4560   -6.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4524   -6.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1666   -7.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1627   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8775   -6.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8785   -6.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5906   -7.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3061   -6.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3050   -6.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5885   -5.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0206   -7.3603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0194   -5.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7339   -6.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0191   -4.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4483   -5.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4480   -4.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4478   -4.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5861   -4.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8706   -4.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8683   -3.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1572   -4.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5817   -3.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2973   -3.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0128   -4.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5948   -6.1309    0.0000 O   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
 14 15  2  0
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4171937

   ---

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: 418.41

Molecular Weight (Monoisotopic): 418.1165

AlogP: 1.84

#Rotatable Bonds: 6

Polar Surface Area: 120.97

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.53

CX Basic pKa: 2.54

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -0.32

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