(1R,SR)1-dodecylsulfinyl-5N,6O-oxomethylidenenojirimycin

ID: ALA4475863

PubChem CID: 155538098

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-CPXLMBNHSA-N

Molfile:  

 
     RDKit          2D

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   12.4147   -6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1200   -6.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8253   -6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8253   -5.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4124   -5.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1200   -5.1549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9498   -4.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1370   -4.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8050   -5.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4965   -3.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7082   -6.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1200   -7.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5324   -6.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5366   -4.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2455   -3.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2479   -3.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9568   -2.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9592   -1.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6681   -1.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3746   -1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3722   -2.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0787   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0763   -3.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7828   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7804   -5.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8180   -4.7504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2387   -5.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6181   -5.7740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  4  5  1  0
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  7  8  1  0
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  9 10  1  0
  6 10  1  0
  8 11  2  0
  5  1  1  0
  2 12  1  6
  3 13  1  1
  4 14  1  6
  1 15  1  0
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 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:

   

   ALA4475863

   ---

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