N-(4-((2R,3R,4S,5R)-4,5-dihydroxy-3-(hydroxymethyl)piperidin-2-yl)butyl)-5-(dimethylamino)naphthalene-1-sulfonamide

ID: ALA3771185

PubChem CID: 127027505

Max Phase: Preclinical

Molecular Formula: C22H33N3O5S

Molecular Weight: 451.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc2c(S(=O)(=O)NCCCC[C@H]3NC[C@@H](O)[C@@H](O)[C@H]3CO)cccc12

Standard InChI:  InChI=1S/C22H33N3O5S/c1-25(2)19-10-5-8-16-15(19)7-6-11-21(16)31(29,30)24-12-4-3-9-18-17(14-26)22(28)20(27)13-23-18/h5-8,10-11,17-18,20,22-24,26-28H,3-4,9,12-14H2,1-2H3/t17-,18+,20+,22-/m0/s1

Standard InChI Key:  LUNDTHLWFREZBS-IKLNAOFOSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.3234    3.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2876    2.9981    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2810    4.1981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   10.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3600   11.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620   12.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   11.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9522   10.4760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6503    9.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   13.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   12.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    9.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   10.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414    8.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    7.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    5.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250    5.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0161    3.7416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -3.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -3.5999    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
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  6
  5 11  1  6
  4 12  1  6
 12 13  1  0
  9 14  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 24  1  0
 23 19  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 23  2  0
 25 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3771185

   ---

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: 451.59

Molecular Weight (Monoisotopic): 451.2141

AlogP: 0.66

#Rotatable Bonds: 9

Polar Surface Area: 122.13

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 9.02

CX LogP: 0.17

CX LogD: -1.13

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: 0.01

References

1. Thonhofer M, Weber P, Santana AG, Fischer R, Pabst BM, Paschke E, Schalli M, Stütz AE, Tschernutter M, Windischhofer W, Withers SG..  (2016)  Synthesis of C-5a-chain extended derivatives of 4-epi-isofagomine: Powerful β-galactosidase inhibitors and low concentration activators of GM1-gangliosidosis-related human lysosomal β-galactosidase.,  26  (5): [PMID:26838810] [10.1016/j.bmcl.2016.01.059]

Source

Source(1):

• Scientific Literature