sodium-(E)-6,6'-(Diazene-1,2-diyl)bis(4-oxo-4H-chromene-2-carboxylate)

ID: ALA2386596

PubChem CID: 71681998

Max Phase: Preclinical

Molecular Formula: C20H8N2Na2O8

Molecular Weight: 406.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])c1cc(=O)c2cc(/N=N/c3ccc4oc(C(=O)[O-])cc(=O)c4c3)ccc2o1.[Na+].[Na+]

Standard InChI:  InChI=1S/C20H10N2O8.2Na/c23-13-7-17(19(25)26)29-15-3-1-9(5-11(13)15)21-22-10-2-4-16-12(6-10)14(24)8-18(30-16)20(27)28;;/h1-8H,(H,25,26)(H,27,28);;/q;2*+1/p-2/b22-21+;;

Standard InChI Key:  GGYDHBICMBNENG-ZPZFBZIMSA-L

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   23.1934   -2.5359    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.8378   -3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8378   -4.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5505   -4.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5505   -2.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2632   -3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2616   -4.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9732   -4.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6870   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6847   -3.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9724   -2.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5505   -2.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1224   -4.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4066   -4.2101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1236   -5.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3984   -2.9627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1150   -3.3734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8288   -2.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8397   -2.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5383   -3.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2592   -2.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5559   -1.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2649   -2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9802   -1.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9926   -0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2836   -0.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5622   -0.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8516   -0.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7149   -0.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4243   -0.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7263    0.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4413   -3.9121    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  3  2  0
  2  5  1  0
  3  4  1  0
  4  7  1  0
  6  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  2  0
 13 14  1  0
 13 15  2  0
  3 13  1  0
 10 16  1  0
 16 17  2  0
 17 18  1  0
 19 18  2  0
 18 20  1  0
 20 21  2  0
 21 23  1  0
 22 19  1  0
 22 23  2  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 29 30  1  0
 29 31  2  0
 25 29  1  0
M  CHG  4   1   1  14  -1  30  -1  32   1
M  END

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: 406.31

Molecular Weight (Monoisotopic): 406.0437

AlogP: 3.71

#Rotatable Bonds: 4

Polar Surface Area: 159.74

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.21

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: -4.03

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: -0.09

References

1. Velema WA, van der Toorn M, Szymanski W, Feringa BL..  (2013)  Design, synthesis, and inhibitory activity of potent, photoswitchable mast cell activation inhibitors.,  56  (11): [PMID:23617679] [10.1021/jm400115k]

2. Velema WA, van der Toorn M, Szymanski W, Feringa BL..  (2013)  Design, synthesis, and inhibitory activity of potent, photoswitchable mast cell activation inhibitors.,  56  (11): [PMID:23617679] [10.1021/jm400115k]

Source

Source(1):

• Scientific Literature