N-((R)-1-Benzothiophen-2-yl(2-chlorophenyl)methyl)cyclopropanesulfonamide

ID: ALA3747326

PubChem CID: 127039286

Max Phase: Preclinical

Molecular Formula: C18H16ClNO2S2

Molecular Weight: 377.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(N[C@@H](c1cc2ccccc2s1)c1ccccc1Cl)C1CC1

Standard InChI:  InChI=1S/C18H16ClNO2S2/c19-15-7-3-2-6-14(15)18(20-24(21,22)13-9-10-13)17-11-12-5-1-4-8-16(12)23-17/h1-8,11,13,18,20H,9-10H2/t18-/m1/s1

Standard InChI Key:  IISHLQHSFRXAQC-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.9203   -2.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202   -2.5626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069   -1.5312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8867   -3.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586   -5.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482   -4.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536   -1.2532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    1.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3204    1.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0517    2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2832    3.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833    3.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0520    2.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9353    0.3377    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    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  1  0
  5  6  1  0
  4  6  1  0
  2  7  1  0
  4  2  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 10 15  1  0
  8  9  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 18 24  2  0
 19 21  2  0
  8 16  1  0
  8  7  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3747326

   ---

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: 377.92

Molecular Weight (Monoisotopic): 377.0311

AlogP: 4.73

#Rotatable Bonds: 5

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -1.36

References

1. Pennington LD, Bartberger MD, Croghan MD, Andrews KL, Ashton KS, Bourbeau MP, Chen J, Chmait S, Cupples R, Fotsch C, Helmering J, Hong FT, Hungate RW, Jordan SR, Kong K, Liu L, Michelsen K, Moyer C, Nishimura N, Norman MH, Reichelt A, Siegmund AC, Sivits G, Tadesse S, Tegley CM, Van G, Yang KC, Yao G, Zhang J, Lloyd DJ, Hale C, St Jean DJ..  (2015)  Discovery and Structure-Guided Optimization of Diarylmethanesulfonamide Disrupters of Glucokinase-Glucokinase Regulatory Protein (GK-GKRP) Binding: Strategic Use of a N → S (nN → σ*S-X) Interaction for Conformational Constraint.,  58  (24): [PMID:26551034] [10.1021/acs.jmedchem.5b01367]

Source

Source(1):

• Scientific Literature