4-Methyl-8-nitro-2-oxo-2H-chromen-7-yl butane-1-sulfonate

ID: ALA4102650

PubChem CID: 137658071

Max Phase: Preclinical

Molecular Formula: C20H19NO7S

Molecular Weight: 417.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1ccc(S(=O)(=O)Oc2ccc3c(C)cc(=O)oc3c2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H19NO7S/c1-3-4-5-14-6-8-15(9-7-14)29(25,26)28-17-11-10-16-13(2)12-18(22)27-20(16)19(17)21(23)24/h6-12H,3-5H2,1-2H3

Standard InChI Key:  VOKQKDCVSRJUEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   27.6566   -2.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0693   -2.8932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.4777   -2.1808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4876   -2.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4865   -2.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1945   -3.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1927   -1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9014   -2.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9047   -2.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6132   -3.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3228   -2.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3194   -2.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6064   -1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6020   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0316   -3.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7785   -3.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3630   -3.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6563   -2.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9505   -3.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9513   -4.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6638   -4.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3667   -4.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2448   -4.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5359   -4.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8294   -4.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1939   -4.1244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9018   -4.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4864   -4.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1205   -4.1270    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  2  0
 13 14  1  0
 11 15  2  0
  5 16  1  0
 16  2  1  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 26 27  2  0
 26 28  1  0
  6 26  1  0
 25 29  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4102650

   ---

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: 417.44

Molecular Weight (Monoisotopic): 417.0882

AlogP: 4.12

#Rotatable Bonds: 7

Polar Surface Area: 116.72

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.09

CX LogD: 5.09

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -0.50

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