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

ID: ALA4172637

PubChem CID: 145949479

Max Phase: Preclinical

Molecular Formula: C26H23N3O7

Molecular Weight: 489.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H23N3O7/c1-3-11-34-22(31)15-19-18-13-16(17-7-8-28-20(14-17)25(32)29-9-10-30)5-6-21(18)36-24(27)23(19)26(33)35-12-4-2/h1-2,5-8,13-14,19,30H,9-12,15,27H2,(H,29,32)

Standard InChI Key:  WOEFSUBHBYXQKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.9609  -27.3705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9598  -28.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6745  -28.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3910  -28.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3881  -27.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6727  -26.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1061  -28.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1024  -29.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8168  -29.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8128  -28.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5276  -28.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5287  -29.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2408  -29.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9562  -29.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9551  -28.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2385  -28.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6707  -29.8392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6692  -27.3629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0984  -28.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0981  -27.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0979  -26.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2363  -27.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5208  -26.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5184  -26.1257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8074  -27.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2318  -25.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9473  -26.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6630  -26.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2449  -28.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5308  -28.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2443  -29.4348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5295  -29.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8154  -29.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1006  -29.8456    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
  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
 10  7  1  0
 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
  2 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4172637

   ---

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: 489.48

Molecular Weight (Monoisotopic): 489.1536

AlogP: 0.86

#Rotatable Bonds: 9

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: ┄

CX Basic pKa: 2.23

CX LogP: 0.98

CX LogD: 0.98

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.34

Np Likeness Score: -0.52

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