Cyclohexyl 2-deoxy-2-C-(2'',3''-epoxypropyl)-alpha-D-glucopyranoside

ID: ALA1088771

PubChem CID: 46885475

Max Phase: Preclinical

Molecular Formula: C15H26O6

Molecular Weight: 302.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](OC2CCCCC2)[C@H](CC2CO2)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H26O6/c16-7-12-14(18)13(17)11(6-10-8-19-10)15(21-12)20-9-4-2-1-3-5-9/h9-18H,1-8H2/t10?,11-,12-,13-,14-,15+/m1/s1

Standard InChI Key:  UMGKHHGSDLSCAF-CIJFKWAFSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.3042    1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    1.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -0.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921   -1.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180   -0.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198    1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331    1.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463    2.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    3.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1533    3.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    3.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769    2.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4512    0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705    0.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409    0.9183    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
 20 19  1  0
 21 20  1  0
 19 21  1  0
  2  3  1  0
  1 10  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1088771

   (2R,3S,4R,5R,6S)-6-cyclohexyloxy-2-(hydroxymethyl)-5-(oxiran-2-ylmethyl)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: 302.37

Molecular Weight (Monoisotopic): 302.1729

AlogP: 0.18

#Rotatable Bonds: 5

Polar Surface Area: 91.68

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: 0.32

CX LogD: 0.32

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.63

Np Likeness Score: 1.90

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