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

ID: ALA4172352

PubChem CID: 145951805

Max Phase: Preclinical

Molecular Formula: C25H21N3O7

Molecular Weight: 475.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3ccnc(NC(=O)CO)c3)cc21

Standard InChI:  InChI=1S/C25H21N3O7/c1-3-9-33-22(31)13-18-17-11-15(16-7-8-27-20(12-16)28-21(30)14-29)5-6-19(17)35-24(26)23(18)25(32)34-10-4-2/h1-2,5-8,11-12,18,29H,9-10,13-14,26H2,(H,27,28,30)

Standard InChI Key:  FHWFDFKNPPZHOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.6722   -6.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3870   -6.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1035   -6.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1006   -5.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3852   -5.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8185   -6.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8150   -7.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5292   -8.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5252   -6.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2401   -6.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2412   -7.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9532   -7.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6687   -7.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6676   -6.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9488   -5.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2332   -5.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2310   -4.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5199   -5.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9442   -3.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6599   -4.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3755   -4.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9574   -6.7684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2433   -6.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5285   -6.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2439   -5.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8143   -6.3542    0.0000 O   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
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  8  9  1  0
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 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
  2 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4172352

   ---

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: 475.46

Molecular Weight (Monoisotopic): 475.1380

AlogP: 1.07

#Rotatable Bonds: 8

Polar Surface Area: 150.07

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: 4.10

CX LogP: 1.23

CX LogD: 1.22

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.38

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