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

ID: ALA4167750

PubChem CID: 145954090

Max Phase: Preclinical

Molecular Formula: C24H20N2O5

Molecular Weight: 416.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H20N2O5/c1-4-10-29-21(27)14-19-18-13-16(17-8-9-26-15(3)12-17)6-7-20(18)31-23(25)22(19)24(28)30-11-5-2/h1-2,6-9,12-13,19H,10-11,14,25H2,3H3

Standard InChI Key:  HLNKVUKTJMCVKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   13.9568  -11.8248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9556  -12.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6704  -13.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3869  -12.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3839  -11.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6686  -11.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1019  -13.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0983  -13.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8127  -14.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8086  -12.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5235  -13.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5246  -13.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2366  -14.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9521  -13.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9510  -13.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2344  -12.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6665  -14.2935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6653  -12.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3799  -13.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6650  -11.8172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0942  -12.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0939  -11.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0937  -10.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2322  -11.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5166  -11.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5143  -10.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8033  -11.8194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2276  -10.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9432  -10.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6589  -10.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2408  -13.0641    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
 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:

   

   ALA4167750

   ---

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: 416.43

Molecular Weight (Monoisotopic): 416.1372

AlogP: 2.45

#Rotatable Bonds: 6

Polar Surface Area: 100.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.85

CX LogP: 2.34

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -0.44

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