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

ID: ALA4169633

PubChem CID: 145953055

Max Phase: Preclinical

Molecular Formula: C24H20N2O5

Molecular Weight: 416.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H20N2O5/c1-4-10-29-21(27)13-19-18-12-16(17-7-6-15(3)26-14-17)8-9-20(18)31-23(25)22(19)24(28)30-11-5-2/h1-2,6-9,12,14,19H,10-11,13,25H2,3H3

Standard InChI Key:  FJIOWWRDPDHWQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.7807  -21.1106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4955  -21.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2120  -21.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2091  -20.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4938  -19.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9271  -21.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9235  -22.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6378  -22.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6337  -21.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3486  -21.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3497  -22.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0617  -22.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7772  -22.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7762  -21.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0595  -21.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4917  -22.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4905  -21.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2051  -21.5129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4903  -20.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9195  -21.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9192  -20.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9189  -19.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0573  -20.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3417  -19.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3395  -19.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6284  -20.2778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0529  -18.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7684  -19.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4840  -19.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0673  -19.8710    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
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  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
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 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:

   

   ALA4169633

   ---

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: 416.43

Molecular Weight (Monoisotopic): 416.1372

AlogP: 2.45

#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: 5.39

CX LogP: 2.34

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.57

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