3-Cyano-4-methyl-2-oxo-2H-chromen-7-yl 3-nitrobenzenesulfonate

ID: ALA4091160

PubChem CID: 137642382

Max Phase: Preclinical

Molecular Formula: C17H10N2O7S

Molecular Weight: 386.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C#N)c(=O)oc2cc(OS(=O)(=O)c3cccc([N+](=O)[O-])c3)ccc12

Standard InChI:  InChI=1S/C17H10N2O7S/c1-10-14-6-5-12(8-16(14)25-17(20)15(10)9-18)26-27(23,24)13-4-2-3-11(7-13)19(21)22/h2-8H,1H3

Standard InChI Key:  FKONMHGNDAFPBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.4863  -19.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8990  -20.2317    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3074  -19.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3174  -19.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3162  -20.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243  -20.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0225  -19.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7311  -19.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7345  -20.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4429  -20.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1525  -20.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1492  -19.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4362  -18.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4317  -18.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8614  -20.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6082  -20.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928  -20.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8515  -18.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5579  -18.5849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860  -20.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7802  -20.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811  -21.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936  -21.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1964  -21.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984  -22.6846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082  -23.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928  -23.0968    0.0000 O   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  2  0
 13 14  1  0
 11 15  2  0
  5 16  1  0
 16  2  1  0
  2 17  1  0
 18 19  3  0
 12 18  1  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 17  1  0
 25 26  2  0
 25 27  1  0
 23 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4091160

   ---

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: 386.34

Molecular Weight (Monoisotopic): 386.0209

AlogP: 2.65

#Rotatable Bonds: 4

Polar Surface Area: 140.51

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -1.17

References

1. Salar U, Khan KM, Iqbal J, Ejaz SA, Hameed A, Al-Rashida M, Perveen S, Tahir MN..  (2017)  Coumarin sulfonates: New alkaline phosphatase inhibitors; in vitro and in silico studies.,  131  [PMID:28288318] [10.1016/j.ejmech.2017.03.003]

Source

Source(1):

• Scientific Literature