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

ID: ALA3800455

PubChem CID: 127047642

Max Phase: Preclinical

Molecular Formula: C20H22N2O5S

Molecular Weight: 402.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC1Oc2ccccc2C(=O)/C1=C\Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C20H22N2O5S/c1-2-3-12-26-20-17(19(23)16-6-4-5-7-18(16)27-20)13-22-14-8-10-15(11-9-14)28(21,24)25/h4-11,13,20,22H,2-3,12H2,1H3,(H2,21,24,25)/b17-13+

Standard InChI Key:  FCRUJYDVTBVQOD-GHRIWEEISA-N

Molfile:  

     RDKit          2D

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    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
    5.1872    3.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1850    5.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2230    5.8586    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
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800455

   ---

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: 402.47

Molecular Weight (Monoisotopic): 402.1249

AlogP: 3.05

#Rotatable Bonds: 7

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: 2.82

CX LogD: 2.82

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.50

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