3-(3-Cyano-5-cyclopropyl-4-hydroxy-benzoyl)-1,1-dioxo-1,2-dihydro-3H-1,3-benzothiazole

ID: ALA4740995

PubChem CID: 51349185

Max Phase: Preclinical

Molecular Formula: C18H14N2O4S

Molecular Weight: 354.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cc(C(=O)N2CS(=O)(=O)c3ccccc32)cc(C2CC2)c1O

Standard InChI:  InChI=1S/C18H14N2O4S/c19-9-13-7-12(8-14(17(13)21)11-5-6-11)18(22)20-10-25(23,24)16-4-2-1-3-15(16)20/h1-4,7-8,11,21H,5-6,10H2

Standard InChI Key:  HJNASESSRLKUIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   41.4869  -16.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4910  -17.7347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.1967  -17.3225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2981  -17.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2969  -18.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0050  -19.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0032  -17.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7118  -17.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7166  -18.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5010  -19.0682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9810  -18.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7580  -19.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2148  -20.4544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.5583  -20.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8106  -20.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6101  -20.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1543  -20.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8934  -19.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0946  -19.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9548  -20.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8688  -21.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1254  -22.5006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4329  -18.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2077  -18.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5953  -18.1474    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
 21 22  3  0
 16 21  1  0
 24 23  1  0
 25 24  1  0
 23 25  1  0
 18 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740995

   3-(3-Cyano-5-cyclopropyl-4-hydroxybenzoyl)-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: 354.39

Molecular Weight (Monoisotopic): 354.0674

AlogP: 2.53

#Rotatable Bonds: 2

Polar Surface Area: 98.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.69

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -0.89

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