(4-Methyl-3-hydroxyphenyl)(6-hydroxy-1,3-benzothiazol-2-yl)methanone

ID: ALA2170754

PubChem CID: 56847605

Max Phase: Preclinical

Molecular Formula: C15H11NO3S

Molecular Weight: 285.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)c2nc3ccc(O)cc3s2)cc1O

Standard InChI:  InChI=1S/C15H11NO3S/c1-8-2-3-9(6-12(8)18)14(19)15-16-11-5-4-10(17)7-13(11)20-15/h2-7,17-18H,1H3

Standard InChI Key:  PJRMJIREEYPPSW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   13.8204   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8204   -8.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6211  -10.3238    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5348   -9.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2885   -9.1678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8406   -9.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4281  -10.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6656   -9.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0781  -10.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6656  -11.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8406  -11.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0781  -11.9243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1059   -9.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3914   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6770   -9.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6770  -10.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3914  -10.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1059  -10.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9625   -9.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9625  -10.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  3  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  7 11  2  0
  6  8  2  0
 10 12  1  0
  1  4  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 15 19  1  0
 16 20  1  0
  1 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2170754

   (6-Hydroxy-1,3-benzothiazol-2-yl)-(3-hydroxy-4-methylphenyl)methanone

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: 285.32

Molecular Weight (Monoisotopic): 285.0460

AlogP: 3.25

#Rotatable Bonds: 2

Polar Surface Area: 70.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.89

CX Basic pKa: 0.27

CX LogP: 3.86

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: -0.64

References

1. Spadaro A, Frotscher M, Hartmann RW..  (2012)  Optimization of hydroxybenzothiazoles as novel potent and selective inhibitors of 17β-HSD1.,  55  (5): [PMID:22277094] [10.1021/jm201711b]

2. Abdelsamie AS, Bey E, Gargano EM, van Koppen CJ, Empting M, Frotscher M..  (2015)  Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme.,  103  [PMID:26322835] [10.1016/j.ejmech.2015.08.030]

Source

Source(1):

• Scientific Literature