2-Hydroxy-4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)-benzoic Acid

ID: ALA4520531

PubChem CID: 7328982

Max Phase: Preclinical

Molecular Formula: C20H14N2O3S

Molecular Weight: 362.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(Nc2nc(-c3ccc4ccccc4c3)cs2)cc1O

Standard InChI:  InChI=1S/C20H14N2O3S/c23-18-10-15(7-8-16(18)19(24)25)21-20-22-17(11-26-20)14-6-5-12-3-1-2-4-13(12)9-14/h1-11,23H,(H,21,22)(H,24,25)

Standard InChI Key:  HUECFCSRZKSRJF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.5364  -26.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1249  -25.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023  -25.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3578  -26.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8370  -27.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6184  -26.8075    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6186  -25.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8373  -25.7335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3258  -25.5723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0410  -25.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439  -26.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7583  -27.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4677  -26.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4582  -25.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7433  -25.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059  -27.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008  -26.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908  -26.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849  -27.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990  -27.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9076  -27.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1651  -25.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1834  -27.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1913  -28.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8871  -26.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4 18  2  0
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  6  7  1  0
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 20 21  1  0
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 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520531

   2-hydroxy-4-[(4-naphthalen-2-yl-1,3-thiazol-2-yl)amino]benzoic Acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.41

Molecular Weight (Monoisotopic): 362.0725

AlogP: 5.11

#Rotatable Bonds: 4

Polar Surface Area: 82.45

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 1.82

CX LogP: 5.59

CX LogD: 2.36

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -1.14

References

1. Bestgen B, Kufareva I, Seetoh W, Abell C, Hartmann RW, Abagyan R, Le Borgne M, Filhol O, Cochet C, Lomberget T, Engel M..  (2019)  2-Aminothiazole Derivatives as Selective Allosteric Modulators of the Protein Kinase CK2. 2. Structure-Based Optimization and Investigation of Effects Specific to the Allosteric Mode of Action.,  62  (4): [PMID:30689946] [10.1021/acs.jmedchem.8b01765]

2. Lindenblatt D, Nickelsen A, Applegate VM, Jose J, Niefind K..  (2020)  Structural and Mechanistic Basis of the Inhibitory Potency of Selected 2-Aminothiazole Compounds on Protein Kinase CK2.,  63  (14): [PMID:32589844] [10.1021/acs.jmedchem.0c00587]

3. Brear P,Ball D,Stott K,D'Arcy S,Hyvönen M.  (2020)  Proposed Allosteric Inhibitors Bind to the ATP Site of CK2α.,  63  (21.0): [PMID:33119282] [10.1021/acs.jmedchem.0c01173]

Source

Source(1):

• Scientific Literature