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

ID: ALA4227083

PubChem CID: 145970892

Max Phase: Preclinical

Molecular Formula: C23H20N2O7S

Molecular Weight: 468.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2c(O)cccc2oc2cc(NS(=O)(=O)c3ccc(N4CCCC4)cc3)c(O)c(O)c12

Standard InChI:  InChI=1S/C23H20N2O7S/c26-16-4-3-5-17-19(16)22(28)20-18(32-17)12-15(21(27)23(20)29)24-33(30,31)14-8-6-13(7-9-14)25-10-1-2-11-25/h3-9,12,24,26-27,29H,1-2,10-11H2

Standard InChI Key:  GDCWTQZIYLQMCS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   17.2972  -21.0447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7099  -21.7546    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1184  -21.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0377  -20.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0366  -21.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7446  -22.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7428  -20.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4514  -20.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4503  -21.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1604  -22.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1627  -20.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8774  -20.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8761  -21.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5854  -22.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2965  -21.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2938  -20.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5839  -20.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1628  -19.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5816  -19.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0000  -20.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0048  -22.1643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4202  -22.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7404  -19.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4191  -22.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1285  -23.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8377  -22.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8329  -22.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1230  -21.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5472  -23.3793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6358  -24.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4358  -24.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8417  -23.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2924  -23.0441    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 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 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  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227083

   ---

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: 468.49

Molecular Weight (Monoisotopic): 468.0991

AlogP: 3.46

#Rotatable Bonds: 4

Polar Surface Area: 140.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.05

CX Basic pKa: 2.53

CX LogP: 5.00

CX LogD: 4.49

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.27

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