4-cyano-N-(1,2,8-trihydroxy-9-oxo-9H-xanthen-3-yl)benzenesulfonamide

ID: ALA4226616

PubChem CID: 145969948

Max Phase: Preclinical

Molecular Formula: C20H12N2O7S

Molecular Weight: 424.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(S(=O)(=O)Nc2cc3oc4cccc(O)c4c(=O)c3c(O)c2O)cc1

Standard InChI:  InChI=1S/C20H12N2O7S/c21-9-10-4-6-11(7-5-10)30(27,28)22-12-8-15-17(20(26)18(12)24)19(25)16-13(23)2-1-3-14(16)29-15/h1-8,22-24,26H

Standard InChI Key:  FNPJGKDSSRCXQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   29.5386  -13.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9513  -13.7849    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.3597  -13.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2791  -12.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2779  -13.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9860  -14.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9842  -12.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6928  -12.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6916  -13.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4017  -14.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4041  -12.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1187  -12.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.8268  -14.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5378  -13.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5351  -12.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8252  -12.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4041  -11.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8229  -11.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2414  -12.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2461  -14.1946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6615  -14.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9817  -11.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6605  -15.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3699  -15.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0790  -15.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0743  -14.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3643  -13.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7870  -15.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4963  -15.8161    0.0000 N   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 11  1  0
  9 10  1  0
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 12 11  1  0
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 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 11 18  2  0
 17 19  1  0
 16 20  1  0
 15 21  1  0
 21  2  1  0
  2 22  1  0
  7 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 29 30  3  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4226616

   ---

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: 424.39

Molecular Weight (Monoisotopic): 424.0365

AlogP: 2.74

#Rotatable Bonds: 3

Polar Surface Area: 160.86

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.60

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 3.51

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.29

Np Likeness Score: -0.22

References

1. Wang P, Jiang L, Cao Y, Zhang X, Chen B, Zhang S, Huang K, Ye D, Zhou L..  (2018)  Xanthone derivatives as phosphoglycerate mutase 1 inhibitors: Design, synthesis, and biological evaluation.,  26  (8): [PMID:29530347] [10.1016/j.bmc.2018.02.044]

Source

Source(1):

• Scientific Literature