Ethanesulfonic acid (S)-((S)-6-cyano-3-hydroxy-2,2-dimethyl-chroman-4-yl)-methyl-amide

ID: ALA44297

Cas Number: 163163-25-5

PubChem CID: 6604863

Product Number: S607164, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H20N2O4S

Molecular Weight: 324.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)N(C)[C@@H]1c2cc(C#N)ccc2OC(C)(C)[C@H]1O

Standard InChI:  InChI=1S/C15H20N2O4S/c1-5-22(19,20)17(4)13-11-8-10(9-16)6-7-12(11)21-15(2,3)14(13)18/h6-8,13-14,18H,5H2,1-4H3/t13-,14+/m1/s1

Standard InChI Key:  HVSJHHXUORMCGK-KGLIPLIRSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    4.5042   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -4.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -5.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -5.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -5.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -5.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -4.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  1  4  1  1
  5  1  1  0
  6  5  1  0
  7  6  1  0
  8  3  1  0
  9 13  3  0
 10  3  2  0
 11  2  2  0
 12  2  2  0
 13 15  1  0
 14  8  2  0
 15 10  1  0
 16  2  1  0
  5 17  1  6
 18 15  2  0
 19  6  1  0
 20  6  1  0
 21  4  1  0
 22 16  1  0
  7  8  1  0
 18 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA44297

   3S,4R-293B

Molecule Features

Natural Product: Yes

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: 324.40

Molecular Weight (Monoisotopic): 324.1144

AlogP: 1.41

#Rotatable Bonds: 3

Polar Surface Area: 90.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: ┄

CX LogP: 0.80

CX LogD: 0.80

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: -0.31

References

1. Wermuth CG..  (2004)  Selective optimization of side activities: another way for drug discovery.,  47  (6): [PMID:14998318] [10.1021/jm030480f]

2. Wermuth CG..  (2004)  Selective optimization of side activities: another way for drug discovery.,  47  (6): [PMID:14998318] [10.1021/jm030480f]

3. Coghlan MJ, Carroll WA, Gopalakrishnan M..  (2001)  Recent developments in the biology and medicinal chemistry of potassium channel modulators: update from a decade of progress.,  44  (11): [PMID:11356099] [10.1021/jm000484+]

4. Gerlach U, Brendel J, Lang HJ, Paulus EF, Weidmann K, Brüggemann A, Busch AE, Suessbrich H, Bleich M, Greger R..  (2001)  Synthesis and activity of novel and selective I(Ks)-channel blockers.,  44  (23): [PMID:11689069] [10.1021/jm0109255]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays