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

ID: ALA4173900

PubChem CID: 145951443

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(-c3ccc(N)nc3)cc21

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

Standard InChI Key:  UVOYFVQXBWGCHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   18.2194  -20.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2181  -21.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9330  -21.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6494  -21.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6466  -20.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9312  -19.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3645  -21.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3609  -22.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0752  -22.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0712  -21.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7860  -21.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7871  -22.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4991  -22.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2147  -22.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2136  -21.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4969  -21.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9291  -22.7519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9279  -21.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6425  -21.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9277  -20.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3569  -21.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3566  -20.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3563  -19.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4947  -20.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7791  -19.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7769  -19.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0658  -20.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4903  -18.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2058  -19.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9214  -19.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5047  -19.8709    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
  1 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173900

   ---

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: 6.34

CX LogP: 1.98

CX LogD: 1.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -0.19

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