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

ID: ALA4585802

PubChem CID: 155566950

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-UBZXTLHSSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   41.8377   -5.3117    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.7204   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4257   -6.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1310   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1310   -5.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7182   -5.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4257   -5.3076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2556   -4.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4428   -4.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1107   -5.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8022   -3.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0139   -6.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4257   -7.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.8381   -6.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.8423   -4.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5512   -4.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5536   -3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2625   -2.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2649   -2.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9738   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6803   -2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6779   -2.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3844   -3.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3820   -4.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0885   -4.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0861   -5.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1237   -4.9031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   42.5444   -5.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.9239   -5.9267    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  1
  6 29  1  6
M  CHG  2   1   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4585802

   ---

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