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

ID: ALA124454

PubChem CID: 11090778

Max Phase: Preclinical

Molecular Formula: C21H27NO5S

Molecular Weight: 405.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)N(C)[C@H]1c2cc(OCc3ccccc3)ccc2OC(C)(C)[C@@H]1O

Standard InChI:  InChI=1S/C21H27NO5S/c1-5-28(24,25)22(4)19-17-13-16(26-14-15-9-7-6-8-10-15)11-12-18(17)27-21(2,3)20(19)23/h6-13,19-20,23H,5,14H2,1-4H3/t19-,20+/m0/s1

Standard InChI Key:  MSKWAZCFXKMVSS-VQTJNVASSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  1  0  0  0  0  0999 V2000
    3.0792   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -2.4875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -2.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -5.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -2.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -1.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -1.6667    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  6
  5  1  1  0
  6  5  1  0
  7  6  1  0
  8  3  1  0
  9  2  2  0
 10  2  2  0
 11  3  2  0
 12  8  2  0
 13 11  1  0
 14  2  1  0
  5 15  1  1
 16 13  1  0
 17 13  2  0
 18 16  1  0
 19  6  1  0
 20  6  1  0
 21  4  1  0
 22 18  1  0
 23 22  2  0
 24 22  1  0
 25 14  1  0
 26 23  1  0
 27 24  2  0
 28 27  1  0
  7  8  1  0
 17 12  1  0
 28 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA124454

   N-[(3R,4S)-3-hydroxy-2,2-dimethyl-6-phenylmethoxy-3,4-dihydrochromen-4-yl]-N-methylethanesulfonamide

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: 405.52

Molecular Weight (Monoisotopic): 405.1610

AlogP: 3.12

#Rotatable Bonds: 6

Polar Surface Area: 76.07

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: 2.51

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.80

Np Likeness Score: -0.08

References

1. 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]

Source

Source(1):

• Scientific Literature