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

ID: ALA4173491

PubChem CID: 145949515

Max Phase: Preclinical

Molecular Formula: C25H23N3O5

Molecular Weight: 445.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H23N3O5/c1-5-11-31-22(29)15-19-18-13-16(17-9-10-27-21(14-17)28(3)4)7-8-20(18)33-24(26)23(19)25(30)32-12-6-2/h1-2,7-10,13-14,19H,11-12,15,26H2,3-4H3

Standard InChI Key:  MBPADZLRXSZUQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.1306  -14.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8453  -14.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5618  -14.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5590  -13.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2770  -14.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -15.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9876  -15.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9835  -14.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.2693  -14.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2690  -13.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2686  -12.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4071  -13.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6915  -12.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6893  -12.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9782  -13.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4027  -11.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1182  -12.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8338  -12.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4158  -14.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7017  -14.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4151  -15.3724    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
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  9 12  2  0
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 15 18  1  0
 18 19  1  0
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 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
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173491

   ---

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: 445.48

Molecular Weight (Monoisotopic): 445.1638

AlogP: 2.20

#Rotatable Bonds: 7

Polar Surface Area: 103.98

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.55

CX LogP: 2.91

CX LogD: 2.86

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: -0.60

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