2-(5-(2,6-Difluoro-3-hydroxybenzoyl)thiophen-2-yl)phenyl sulfamate

ID: ALA4088890

PubChem CID: 137643959

Max Phase: Preclinical

Molecular Formula: C17H11F2NO5S2

Molecular Weight: 411.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)Oc1ccccc1-c1ccc(C(=O)c2c(F)ccc(O)c2F)s1

Standard InChI:  InChI=1S/C17H11F2NO5S2/c18-10-5-6-11(21)16(19)15(10)17(22)14-8-7-13(26-14)9-3-1-2-4-12(9)25-27(20,23)24/h1-8,21H,(H2,20,23,24)

Standard InChI Key:  KQHDOCJPMHAEJX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.7378   -8.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4477   -8.9561    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4466   -8.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5320  -11.4004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2588  -11.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9692  -11.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0641  -10.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8688  -10.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2722  -11.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0903  -11.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4845  -10.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3026  -10.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7312  -11.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3376  -11.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5189  -11.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7161  -11.7153    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2519  -12.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9555  -13.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6700  -12.6103    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9486  -13.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2341  -14.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5305  -13.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8160  -14.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5374  -13.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8297  -12.5847    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0591   -9.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2675   -8.9379    0.0000 N   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  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
  9 16  1  0
  6 16  1  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 17 24  1  0
 24 25  1  0
 11 26  1  0
 26  2  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088890

   ---

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: 411.41

Molecular Weight (Monoisotopic): 411.0047

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 106.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.45

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -0.70

References

1. Salah M, Abdelsamie AS, Frotscher M..  (2017)  First Dual Inhibitors of Steroid Sulfatase (STS) and 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1): Designed Multiple Ligands as Novel Potential Therapeutics for Estrogen-Dependent Diseases.,  60  (9): [PMID:28406629] [10.1021/acs.jmedchem.7b00062]

Source

Source(1):

• Scientific Literature