2,6-Difluoro-3-hydroxy-N-(6-hydroxy-1,3-benzothiazol-2-yl)benzamide

ID: ALA2170747

PubChem CID: 56929159

Max Phase: Preclinical

Molecular Formula: C14H8F2N2O3S

Molecular Weight: 322.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccc(O)cc2s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C14H8F2N2O3S/c15-7-2-4-9(20)12(16)11(7)13(21)18-14-17-8-3-1-6(19)5-10(8)22-14/h1-5,19-20H,(H,17,18,21)

Standard InChI Key:  WAIPUKHVRXNDDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.4416  -10.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6166  -10.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2041   -9.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3791   -9.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9666  -10.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3791  -10.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2041  -10.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8541   -9.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8541  -10.7818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1641  -11.4493    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6791  -10.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1641  -10.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9487  -10.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9487  -11.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6632   -9.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776  -10.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776  -11.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6632  -11.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0921  -11.6068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9666   -8.6384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6166  -11.4963    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6166   -8.6384    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 10 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 14 18  2  0
 13 15  2  0
 17 19  1  0
  9 11  1  0
  4 20  1  0
  7 21  1  0
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2170747

   2,6-difluoro-3-hydroxy-N-(6-hydroxy-1,3-benzothiazol-2-yl)benzamide

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: 322.29

Molecular Weight (Monoisotopic): 322.0224

AlogP: 3.24

#Rotatable Bonds: 2

Polar Surface Area: 82.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -1.74

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]

Source

Source(1):

• Scientific Literature