(rac)-4-({(Z)-[4-oxo-2-(propan-2-yloxy)-2H-chromen-3(4H)-ylidene]methyl}amino)benzenesulfonamide

ID: ALA3798555

PubChem CID: 127047759

Max Phase: Preclinical

Molecular Formula: C19H20N2O5S

Molecular Weight: 388.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC1Oc2ccccc2C(=O)/C1=C\Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C19H20N2O5S/c1-12(2)25-19-16(18(22)15-5-3-4-6-17(15)26-19)11-21-13-7-9-14(10-8-13)27(20,23)24/h3-12,19,21H,1-2H3,(H2,20,23,24)/b16-11+

Standard InChI Key:  PMFOXZVNMQLVKT-LFIBNONCSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.1123   -7.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1066   -5.9794    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1432   -5.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982   -2.9972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1995   -3.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058   -5.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5078   -5.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8038   -5.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7977   -3.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956   -2.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    3.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1486   -6.5747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270    3.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8487    3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 12 15  1  0
 11 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 24  1  0
 21  2  1  0
  2 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3798555

   ---

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: 388.45

Molecular Weight (Monoisotopic): 388.1093

AlogP: 2.66

#Rotatable Bonds: 5

Polar Surface Area: 107.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.82

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.46

References

1. al-Rashida M, Batool G, Sattar A, Ejaz SA, Khan S, Lecka J, Sévigny J, Hameed A, Iqbal J..  (2016)  2-Alkoxy-3-(sulfonylarylaminomethylene)-chroman-4-ones as potent and selective inhibitors of ectonucleotidases.,  115  [PMID:27054295] [10.1016/j.ejmech.2016.02.073]

Source

Source(1):

• Scientific Literature