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

ID: ALA4167314

PubChem CID: 145952732

Max Phase: Preclinical

Molecular Formula: C22H19N3O5

Molecular Weight: 405.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOC(=O)CC1C(C(=O)OCC#C)=C(N)Oc2ccc(-c3cnn(C)c3)cc21

Standard InChI:  InChI=1S/C22H19N3O5/c1-4-8-28-19(26)11-17-16-10-14(15-12-24-25(3)13-15)6-7-18(16)30-21(23)20(17)22(27)29-9-5-2/h1-2,6-7,10,12-13,17H,8-9,11,23H2,3H3

Standard InChI Key:  NHSIUZUXAMTREQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.6110   -5.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3253   -6.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213   -4.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361   -5.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372   -5.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493   -6.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4648   -5.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4636   -5.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7471   -4.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1780   -4.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8927   -5.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1778   -3.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6069   -4.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6067   -3.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6064   -2.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0293   -3.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7404   -2.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560   -2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1715   -2.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998   -4.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163   -3.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -3.6392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -4.3541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1499   -4.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729   -2.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
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  8  9  2  0
  9 10  1  0
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  9 12  1  0
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 16 17  3  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  3  0
  1 25  1  0
 25 26  2  0
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 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4167314

   ---

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: 405.41

Molecular Weight (Monoisotopic): 405.1325

AlogP: 1.48

#Rotatable Bonds: 6

Polar Surface Area: 105.67

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.83

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -0.92

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