sodium 2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoate

ID: ALA5195075

PubChem CID: 21365319

Max Phase: Preclinical

Molecular Formula: C20H11NaO5

Molecular Weight: 332.31

Names and Identifiers

Canonical SMILES:  O=C([O-])c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12.[Na+]

Standard InChI:  InChI=1S/C20H12O5.Na/c21-11-5-7-15-17(9-11)25-18-10-12(22)6-8-16(18)19(15)13-3-1-2-4-14(13)20(23)24;/h1-10,21H,(H,23,24);/q;+1/p-1

Standard InChI Key:  BVBBXLSCRWJFHQ-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.9135   -1.0996    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.7695    1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    2.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737    2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882    1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882    0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872    2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594   -0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6586   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -1.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729   -0.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8030    2.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0888   -0.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905    0.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    2.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  3  1  0
  5  4  1  0
  6  5  2  0
  2  7  2  0
  7  6  1  0
  4  8  2  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
  5 11  1  0
  7 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
  2 15  1  0
 16  6  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 16 21  1  0
 21 20  2  0
  9 22  2  0
 17 23  1  0
 23 24  1  0
 23 25  2  0
 14 26  1  0
M  CHG  2   1   1  24  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 332.31

Molecular Weight (Monoisotopic): 332.0685

AlogP: 3.97

#Rotatable Bonds: 2

Polar Surface Area: 87.74

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: 2.85

CX LogP: 2.65

CX LogD: -1.30

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 0.59

References

1. McCoy MA, Spicer D, Wells N, Hoogewijs K, Fiedler M, Baud MGJ..  (2022)  Biophysical Survey of Small-Molecule β-Catenin Inhibitors: A Cautionary Tale.,  65  (10.0): [PMID:35581674] [10.1021/acs.jmedchem.2c00228]

Source

Source(1):

• Scientific Literature