Prop-2-yn-1-yl-2-Amino-6-(5-aminopyridin-3-yl)-4-(2-oxo-2-(prop-2-yn-1-yloxy)ethyl)-4H-chromene-3-carboxylate

ID: ALA4170701

PubChem CID: 145951321

Max Phase: Preclinical

Molecular Formula: C23H19N3O5

Molecular Weight: 417.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3cncc(N)c3)cc21

Standard InChI:  InChI=1S/C23H19N3O5/c1-3-7-29-20(27)11-18-17-10-14(15-9-16(24)13-26-12-15)5-6-19(17)31-22(25)21(18)23(28)30-8-4-2/h1-2,5-6,9-10,12-13,18H,7-8,11,24-25H2

Standard InChI Key:  WDLZRMDUPKYHGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    1.7485  -12.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474  -13.0605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622  -13.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787  -13.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1758  -12.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604  -11.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937  -13.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902  -14.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6044  -14.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004  -13.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153  -13.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3164  -14.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284  -14.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439  -14.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7428  -13.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0262  -13.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4583  -14.7019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4571  -13.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1717  -13.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4568  -12.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8860  -13.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8858  -12.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8855  -11.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0240  -12.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084  -11.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3062  -10.9883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950  -12.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194  -10.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7351  -10.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4506  -11.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579  -10.9955    0.0000 N   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
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4170701

   ---

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: 417.42

Molecular Weight (Monoisotopic): 417.1325

AlogP: 1.72

#Rotatable Bonds: 6

Polar Surface Area: 126.76

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.35

CX LogP: 1.38

CX LogD: 1.38

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -0.49

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