Cyclohexyl 2-deoxy-2-C-(2''-hydroxypropyl)-alpha-D-glucopyranoside

ID: ALA1090142

PubChem CID: 46885409

Max Phase: Preclinical

Molecular Formula: C15H28O6

Molecular Weight: 304.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(O)C[C@H]1[C@@H](OC2CCCCC2)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H28O6/c1-9(17)7-11-13(18)14(19)12(8-16)21-15(11)20-10-5-3-2-4-6-10/h9-19H,2-8H2,1H3/t9?,11-,12-,13-,14-,15+/m1/s1

Standard InChI Key:  PJDNUTKOHPACDR-ZMPBYDAFSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   14.2542  -25.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2542  -26.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9662  -26.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6782  -26.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6782  -25.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9662  -25.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3921  -26.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9662  -27.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5403  -26.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5385  -25.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8252  -25.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3939  -25.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3963  -24.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1120  -23.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1164  -23.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4050  -22.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6875  -22.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6814  -23.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1071  -26.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8210  -26.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1083  -25.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 10 11  1  0
  4  5  1  0
  5 12  1  6
  5  6  1  0
 12 13  1  0
 13 14  1  0
  4  7  1  6
  1  2  1  0
  3  8  1  1
  1  6  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  2  9  1  6
  7 19  1  0
  2  3  1  0
 19 20  1  0
  1 10  1  1
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090142

   (2R,3S,4R,5R,6S)-6-cyclohexyloxy-2-(hydroxymethyl)-5-(2-hydroxypropyl)oxane-3,4-diol

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: 304.38

Molecular Weight (Monoisotopic): 304.1886

AlogP: 0.16

#Rotatable Bonds: 5

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.02

CX Basic pKa: ┄

CX LogP: 0.21

CX LogD: 0.21

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 1.97

References

1. Gammon DW, Steenkamp DJ, Mavumengwana V, Marakalala MJ, Mudzunga TT, Hunter R, Munyololo M..  (2010)  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol.,  18  (7): [PMID:20304659] [10.1016/j.bmc.2010.02.049]

Source

Source(1):

• Scientific Literature