IMPPAT Phytochemical information: 
(2R,3R,4S,5S,6R)-2-(furan-3-ylmethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

(2R,3R,4S,5S,6R)-2-(furan-3-ylmethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Summary

SMILES: OC[C@H]1O[C@@H](OCc2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C11H16O7/c12-3-7-8(13)9(14)10(15)11(18-7)17-5-6-1-2-16-4-6/h1-2,4,7-15H,3,5H2/t7-,8-,9+,10-,11-/m1/s1
InChIKey: SPFOGLIFWSAONR-KAMPLNKDSA-N
DeepSMILES: OC[C@H]O[C@@H]OCccocc5)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1cc(COC2CCCCO2)co1
Scaffold Graph/Node level: C1CCC(OCC2CCOC2)OC1
Scaffold Graph level: C1CCC(CCC2CCCC2)CC1
Functional groups: CO; CO[C@@H](C)OC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
beta-furfuryl-beta-glucoside
External chemical identifiers:
CID:CID_3086224
Chemical structure download


(2R,3R,4S,5S,6R)-2-(furan-3-ylmethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 260.24
Log P RDKit -1.4
Topological polar surface area (Å2) RDKit 112.52
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


(2R,3R,4S,5S,6R)-2-(furan-3-ylmethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53


(2R,3R,4S,5S,6R)-2-(furan-3-ylmethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.04
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No