(rac)-4-{[(Z)-(6-chloro-2-methoxy-4-oxo-2H-chromen-3(4H)-ylidene)methyl]amino}benzenesulfonamide

ID: ALA3797640

PubChem CID: 127047727

Max Phase: Preclinical

Molecular Formula: C17H15ClN2O5S

Molecular Weight: 394.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1Oc2ccc(Cl)cc2C(=O)/C1=C\Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C17H15ClN2O5S/c1-24-17-14(16(21)13-8-10(18)2-7-15(13)25-17)9-20-11-3-5-12(6-4-11)26(19,22)23/h2-9,17,20H,1H3,(H2,19,22,23)/b14-9+

Standard InChI Key:  MOSIWAHMPGPLCK-NTEUORMPSA-N

Molfile:  

     RDKit          2D

 26 28  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
    3.8894    2.7017    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
   -3.6486   -1.3517    0.0000 Cl  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
  5 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797640

   ---

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: 394.84

Molecular Weight (Monoisotopic): 394.0390

AlogP: 2.53

#Rotatable Bonds: 4

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: 2.10

CX LogD: 2.10

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -0.64

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