(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(octyloxy)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA446037

Cas Number: 29836-26-8

PubChem CID: 62852

Product Number: O105509, Order Now?

Max Phase: Preclinical

Molecular Formula: C14H28O6

Molecular Weight: 292.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Octyl Beta-D-Glucoside | 29836-26-8|Octyl-beta-D-glucopyranoside|OCTYL BETA-D-GLUCOPYRANOSIDE|B-Octylglucoside|n-Octyl-beta-D-glucopyranoside|1-O-n-Octyl-beta-D-glucopyranoside|Octyl beta-D-glucoside|Octyl glucoside|caprylyl glucoside|n-Octyl glucoside|(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(octyloxy)tetrahydro-2H-pyran-3,4,5-triol|beta-D-Octyl glucoside|Octyl-beta-D-glucoside|1-O-Octyl-beta-D-glucopyranoside|(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-octoxyoxane-3,4,5-triol|n-Octyl beta-D-glucopyranosiShow More⌵

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

Standard InChI:  InChI=1S/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14-/m1/s1

Standard InChI Key:  HEGSGKPQLMEBJL-RKQHYHRCSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.0736    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591    0.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -1.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.8970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -1.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880    0.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    1.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  1  3  1  0
  1 10  1  0
 13  2  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA446037

   N-Octyl-β-D-glucopyranoside

Molecule Features

Natural Product: Yes

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: 292.37

Molecular Weight (Monoisotopic): 292.1886

AlogP: 0.16

#Rotatable Bonds: 9

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: 12.21

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: 0.81

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 1.81

References

1. Randhawa P, Farasati NA, Huang Y..  (2007)  BK Virus replication in vitro: limited effect of drugs interfering with viral uptake and intracellular transport.,  51  (12): [PMID:17893158] [10.1128/aac.00843-07]

2. Lairson LL, Watts AG, Wakarchuk WW, Withers SG..  (2006)  Using substrate engineering to harness enzymatic promiscuity and expand biological catalysis.,  2  (12): [PMID:17057723] [10.1038/nchembio828]

3. PubChem BioAssay data set, 

4. Nkosana NK, Czyzyk DJ, Siegel ZS, Cote JM, Taylor EA..  (2018)  Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.,  28  (4): [PMID:29398539] [10.1016/j.bmcl.2018.01.040]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays