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

ID: ALA4170045

PubChem CID: 145955354

Max Phase: Preclinical

Molecular Formula: C24H21N3O5

Molecular Weight: 431.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H21N3O5/c1-4-10-30-21(28)14-18-17-12-15(16-8-9-27-20(13-16)26-3)6-7-19(17)32-23(25)22(18)24(29)31-11-5-2/h1-2,6-9,12-13,18H,10-11,14,25H2,3H3,(H,26,27)

Standard InChI Key:  SGPRRKBDEKPRHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   29.3524   -5.3957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3513   -6.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0661   -6.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7825   -6.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7796   -5.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0642   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4976   -6.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4941   -7.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2083   -7.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2043   -6.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9191   -6.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9202   -7.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6323   -7.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3477   -7.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3466   -6.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6301   -6.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0622   -7.8645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0610   -6.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7755   -6.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0607   -5.3881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4899   -6.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4897   -5.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4894   -4.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6278   -5.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9123   -4.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9099   -4.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1989   -5.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6233   -3.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3390   -4.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0545   -4.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6364   -6.6350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9223   -6.2219    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
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4170045

   ---

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: 431.45

Molecular Weight (Monoisotopic): 431.1481

AlogP: 2.18

#Rotatable Bonds: 7

Polar Surface Area: 112.77

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.71

CX LogP: 2.28

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -0.43

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