Cyclohexyl 2-deoxy-2-C-propyl-alpha-D-glucopyranoside

ID: ALA1088821

PubChem CID: 46885408

Max Phase: Preclinical

Molecular Formula: C15H28O5

Molecular Weight: 288.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H28O5/c1-2-6-11-13(17)14(18)12(9-16)20-15(11)19-10-7-4-3-5-8-10/h10-18H,2-9H2,1H3/t11-,12-,13-,14-,15+/m1/s1

Standard InChI Key:  VLMLGSXLIFLFAE-RYPNDVFKSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    8.3833  -25.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3833  -26.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0954  -26.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8074  -26.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8074  -25.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0954  -25.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5212  -26.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0954  -27.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6695  -26.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677  -25.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9544  -25.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5230  -25.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5255  -24.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2412  -23.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2456  -23.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5342  -22.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8167  -23.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8106  -23.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2363  -26.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9502  -26.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  1
  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
M  END

Alternative Forms

1. Parent:

   

   ALA1088821

   (2R,3S,4R,5R,6S)-6-cyclohexyloxy-2-(hydroxymethyl)-5-propyloxane-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: 288.38

Molecular Weight (Monoisotopic): 288.1937

AlogP: 1.19

#Rotatable Bonds: 5

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.02

CX Basic pKa: ┄

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: 1.89

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