3-(4-Hydroxy-3-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-1,2-dihydro-3H-1,3-benzothiazole

ID: ALA4762003

PubChem CID: 68108876

Max Phase: Preclinical

Molecular Formula: C16H12F3NO5S

Molecular Weight: 387.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)N2CS(=O)(=O)c3ccccc32)cc(C(F)(F)F)c1O

Standard InChI:  InChI=1S/C16H12F3NO5S/c1-25-12-7-9(6-10(14(12)21)16(17,18)19)15(22)20-8-26(23,24)13-5-3-2-4-11(13)20/h2-7,21H,8H2,1H3

Standard InChI Key:  KHNOOWVYFIYSGN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.5140  -18.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181  -19.1916    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237  -18.7794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251  -19.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240  -20.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320  -20.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302  -19.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7389  -19.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437  -20.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5281  -20.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0081  -19.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7851  -21.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419  -21.9113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5854  -21.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8377  -22.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6372  -22.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1814  -21.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9205  -21.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1216  -20.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9819  -21.9629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4616  -20.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2625  -20.5699    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.2018  -19.6326    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0386  -19.8231    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8939  -23.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6941  -23.3510    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
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2  8  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 16 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762003

   3-(4-Hydroxy-3-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole

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: 387.33

Molecular Weight (Monoisotopic): 387.0388

AlogP: 2.81

#Rotatable Bonds: 2

Polar Surface Area: 83.91

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.98

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -0.83

References

1. Uda J,Kobashi S,Miyata S,Ashizawa N,Matsumoto K,Iwanaga T.  (2020)  Discovery of Dotinurad (FYU-981), a New Phenol Derivative with Highly Potent Uric Acid Lowering Activity.,  11  (10): [PMID:33062187] [10.1021/acsmedchemlett.0c00176]

Source

Source(1):

• Scientific Literature