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

ID: ALA4177495

PubChem CID: 145971538

Max Phase: Preclinical

Molecular Formula: C23H17FN2O5

Molecular Weight: 420.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3ccc(F)nc3)cc21

Standard InChI:  InChI=1S/C23H17FN2O5/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

Standard InChI Key:  WICQZGVNKVINKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.6485  -28.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6473  -28.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3621  -29.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0785  -28.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0757  -28.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603  -27.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7937  -29.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7900  -30.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5043  -30.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5003  -28.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2152  -29.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2163  -30.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9282  -30.6217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6438  -30.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6427  -29.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9261  -28.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3583  -30.6225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3570  -28.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0716  -29.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3567  -28.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7860  -28.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7857  -28.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7855  -27.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9238  -28.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2082  -27.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2060  -26.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4949  -28.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9194  -26.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6349  -26.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3505  -27.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9339  -27.7415    0.0000 F   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:

   

   ALA4177495

   ---

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: 420.40

Molecular Weight (Monoisotopic): 420.1121

AlogP: 2.28

#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: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.59

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