(1R,SS)-1-Dodecylsulfinyl-5N,6O-oxomethylidenegalactonojirimycin

ID: ALA4589470

PubChem CID: 155569212

Max Phase: Preclinical

Molecular Formula: C19H35NO6S

Molecular Weight: 405.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC[S@+]([O-])[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H]2COC(=O)N21

Standard InChI:  InChI=1S/C19H35NO6S/c1-2-3-4-5-6-7-8-9-10-11-12-27(25)18-17(23)16(22)15(21)14-13-26-19(24)20(14)18/h14-18,21-23H,2-13H2,1H3/t14-,15+,16+,17-,18-,27+/m1/s1

Standard InChI Key:  USUBBLBZXUZTKN-OWFQYJTESA-N

Molfile:  

 
     RDKit          2D

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   32.8445   -4.7215    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.7272   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4325   -6.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1378   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1378   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7249   -5.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4325   -4.7174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2623   -3.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4495   -3.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1175   -4.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8090   -3.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0207   -6.3579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4325   -7.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8449   -6.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8491   -3.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5580   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5604   -2.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2693   -2.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2717   -1.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9806   -1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6871   -1.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6847   -2.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3912   -2.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3888   -3.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0953   -3.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0929   -4.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1305   -4.3130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.5512   -5.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9059   -5.1219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
  8 11  2  0
  5  1  1  0
  2 12  1  1
  3 13  1  1
  4 14  1  6
  1 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  5 27  1  1
  1 28  1  6
  6 29  1  6
M  CHG  2   1   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4589470

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.56

Molecular Weight (Monoisotopic): 405.2185

AlogP: 1.90

#Rotatable Bonds: 12

Polar Surface Area: 113.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.67

CX Basic pKa: ┄

CX LogP: 1.87

CX LogD: 1.87

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: 0.52

References

1. Schaeffer E, Sánchez-Fernández EM, Gonçalves-Pereira R, Flacher V, Lamon D, Duval M, Fauny JD, García Fernández JM, Mueller CG, Ortiz Mellet C..  (2019)  sp²-Iminosugar glycolipids as inhibitors of lipopolysaccharide-mediated human dendritic cell activation in vitro and of acute inflammation in mice in vivo.,  169  [PMID:30870792] [10.1016/j.ejmech.2019.02.078]

Source

Source(1):

• Scientific Literature