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

ID: ALA4170503

PubChem CID: 145955617

Max Phase: Preclinical

Molecular Formula: C23H18N2O5

Molecular Weight: 402.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3ccncc3)cc21

Standard InChI:  InChI=1S/C23H18N2O5/c1-3-11-28-20(26)14-18-17-13-16(15-7-9-25-10-8-15)5-6-19(17)30-22(24)21(18)23(27)29-12-4-2/h1-2,5-10,13,18H,11-12,14,24H2

Standard InChI Key:  HWLLPTXUODIEBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.8403   -4.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -5.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5539   -5.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2703   -5.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2675   -4.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521   -4.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9855   -5.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9819   -6.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -7.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6922   -5.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4069   -5.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080   -6.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -7.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8357   -6.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8346   -5.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1179   -5.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5500   -7.0603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -5.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2635   -5.8213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5486   -4.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9778   -5.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9775   -4.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9772   -3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1156   -4.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4001   -4.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3979   -3.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6867   -4.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1112   -2.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8268   -3.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5423   -3.7534    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
  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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA4170503

   ---

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: 402.41

Molecular Weight (Monoisotopic): 402.1216

AlogP: 2.14

#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: 5.14

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -0.46

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