2-amino-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)-4-(3-methoxyphenyl)nicotinonitrile

ID: ALA4868909

PubChem CID: 164625158

Max Phase: Preclinical

Molecular Formula: C22H15N3O4

Molecular Weight: 385.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cc(-c3c(O)c4ccccc4oc3=O)nc(N)c2C#N)c1

Standard InChI:  InChI=1S/C22H15N3O4/c1-28-13-6-4-5-12(9-13)15-10-17(25-21(24)16(15)11-23)19-20(26)14-7-2-3-8-18(14)29-22(19)27/h2-10,26H,1H3,(H2,24,25)

Standard InChI Key:  ZHSQXZZMKDUQLK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.0462   -6.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616   -7.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598   -5.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -5.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764   -6.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1923   -7.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9078   -6.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -5.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -5.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6084   -5.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3262   -5.9290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0381   -5.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0336   -4.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111   -4.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6021   -4.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037   -3.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0163   -3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0088   -2.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2894   -1.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761   -2.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -3.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -7.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -4.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -4.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4571   -3.8505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7554   -5.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154   -1.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4305   -2.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
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  6  7  1  0
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  9 10  2  0
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 11 12  2  0
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  9 11  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 15 17  1  0
  8 23  2  0
 10 24  1  0
 25 26  3  0
 14 25  1  0
 13 27  1  0
 19 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4868909

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 385.38

Molecular Weight (Monoisotopic): 385.1063

AlogP: 3.69

#Rotatable Bonds: 3

Polar Surface Area: 122.37

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.96

CX Basic pKa: 0.84

CX LogP: 2.98

CX LogD: 1.54

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -0.49

References

1. Ahmed EY, Elserwy WS, El-Mansy MF, Serry AM, Salem AM, Abdou AM, Abdelrahman BA, Elsayed KH, Abd Elaziz MR..  (2021)  Angiokinase inhibition of VEGFR-2, PDGFR and FGFR and cell growth inhibition in lung cancer: Design, synthesis, biological evaluation and molecular docking of novel azaheterocyclic coumarin derivatives.,  48  [PMID:34246754] [10.1016/j.bmcl.2021.128258]

Source

Source(1):

• Scientific Literature