N-(6-Benzyloxy-3-hydroxy-2,2-dimethyl-chroman-4-yl)-N-methyl-methanesulfonamide

ID: ALA124308

PubChem CID: 11760985

Max Phase: Preclinical

Molecular Formula: C20H25NO5S

Molecular Weight: 391.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C1c2cc(OCc3ccccc3)ccc2OC(C)(C)C1O)S(C)(=O)=O

Standard InChI:  InChI=1S/C20H25NO5S/c1-20(2)19(22)18(21(3)27(4,23)24)16-12-15(10-11-17(16)26-20)25-13-14-8-6-5-7-9-14/h5-12,18-19,22H,13H2,1-4H3

Standard InChI Key:  WHSNUPSZOQRQAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    4.5167   -3.7292    0.0000 O   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
    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
   -1.9083   -2.5000    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
   -1.9125   -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
  4  1  1  0
  5  1  1  0
  6  5  1  0
  7  6  1  0
  8  3  1  0
  9  2  2  0
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 13 11  1  0
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 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
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 26 23  1  0
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  7  8  1  0
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 27 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA124308

   N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

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: 391.49

Molecular Weight (Monoisotopic): 391.1453

AlogP: 2.73

#Rotatable Bonds: 5

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: 2.00

CX LogD: 2.00

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: 0.06

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