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

ID: ALA4176850

PubChem CID: 145973171

Max Phase: Preclinical

Molecular Formula: C25H21N3O6

Molecular Weight: 459.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H21N3O6/c1-4-10-32-22(30)14-19-18-12-16(17-8-9-27-21(13-17)28-15(3)29)6-7-20(18)34-24(26)23(19)25(31)33-11-5-2/h1-2,6-9,12-13,19H,10-11,14,26H2,3H3,(H,27,28,29)

Standard InChI Key:  WBWJCLQZAFRHTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   27.8691  -27.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8680  -28.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5827  -28.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2992  -28.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2963  -27.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5809  -26.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0143  -28.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0107  -29.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7250  -29.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7210  -28.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4358  -28.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4369  -29.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1490  -29.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8644  -29.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8633  -28.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1467  -28.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5789  -29.8100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5777  -28.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2922  -28.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5774  -27.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0066  -28.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0064  -27.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0061  -26.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1445  -27.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4289  -26.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4266  -26.0965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7156  -27.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1400  -25.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8556  -26.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5712  -26.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1531  -28.5806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4391  -28.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7242  -28.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4397  -27.3426    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
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176850

   ---

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: 459.46

Molecular Weight (Monoisotopic): 459.1430

AlogP: 2.10

#Rotatable Bonds: 7

Polar Surface Area: 129.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: 4.14

CX LogP: 2.04

CX LogD: 2.04

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.48

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