(Z)-4-(3-chloro-4-fluorobenzyl)-6-((4-oxo-2-thioxothiazolidin-5-ylidene)methyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA3922359

PubChem CID: 134140359

Max Phase: Preclinical

Molecular Formula: C19H12ClFN2O3S2

Molecular Weight: 434.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=S)S/C1=C\c1ccc2c(c1)N(Cc1ccc(F)c(Cl)c1)C(=O)CO2

Standard InChI:  InChI=1S/C19H12ClFN2O3S2/c20-12-5-11(1-3-13(12)21)8-23-14-6-10(2-4-15(14)26-9-17(23)24)7-16-18(25)22-19(27)28-16/h1-7H,8-9H2,(H,22,25,27)/b16-7-

Standard InChI Key:  KWDKVVZOYYHCRG-APSNUPSMSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.1901   -3.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997   -2.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1883   -1.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -2.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816   -2.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756   -1.6068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -2.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -2.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -3.2460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -3.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6081   -3.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3152   -2.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0586   -3.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6044   -2.5528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1947   -1.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3957   -2.0170    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2295   -3.9601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5258   -1.0986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779   -4.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -4.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834   -5.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910   -5.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -5.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8948   -4.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -4.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922   -6.5124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6080   -5.6916    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 14 18  2  0
 16 19  2  0
 10 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3922359

   ---

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: 434.90

Molecular Weight (Monoisotopic): 433.9962

AlogP: 3.89

#Rotatable Bonds: 3

Polar Surface Area: 58.64

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.99

References

1. Falasca M, Hamilton JR, Selvadurai M, Sundaram K, Adamska A, Thompson PE..  (2017)  Class II Phosphoinositide 3-Kinases as Novel Drug Targets.,  60  (1): [PMID:27644332] [10.1021/acs.jmedchem.6b00963]

Source

Source(1):

• Scientific Literature