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

ID: ALA1093314

PubChem CID: 46885410

Max Phase: Preclinical

Molecular Formula: C15H26O6

Molecular Weight: 302.37

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/C15H26O6/c1-9(17)7-11-13(18)14(19)12(8-16)21-15(11)20-10-5-3-2-4-6-10/h10-16,18-19H,2-8H2,1H3/t11-,12-,13-,14-,15+/m1/s1

Standard InChI Key:  OIWOHXUFYAMPDJ-RYPNDVFKSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   20.3792  -25.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3792  -26.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0912  -26.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8032  -26.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8032  -25.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0912  -24.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5171  -26.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0912  -27.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6653  -26.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6635  -24.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9502  -25.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5189  -24.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5213  -24.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2370  -23.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2414  -22.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5300  -22.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8125  -22.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8064  -23.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2321  -26.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9460  -26.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2333  -25.2521    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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093314

   1-[(2S,3R,4R,5S,6R)-2-cyclohexyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]propan-2-one

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: 302.37

Molecular Weight (Monoisotopic): 302.1729

AlogP: 0.37

#Rotatable Bonds: 5

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.02

CX Basic pKa: ┄

CX LogP: 0.24

CX LogD: 0.24

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 1.96

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