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2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose

PubChem CID: 441426

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Compound Synonyms 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose, C08244, alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose, Neohesperidoside, AC1L9B54, 2-O-alpha-L-Rhamnosyl-D-glucose, SureCN6521257, Ambap17074-02-1, SCHEMBL6521257, CHEBI:73992, 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranose, alpha-L-Rhap-(1->2)-beta-D-Glcp, 2-O-alpha-l-rhamnosyl-beta-d-glucose, 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranose, Q3347120, 6-deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-glucopyranose, (2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,4,5-triol, (2S,3R,4R,5R,6S)-2-methyl-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]oxy-tetrahydropyran-3,4,5-triol
Topological Polar Surface Area 169.0
Hydrogen Bond Donor Count 7.0
Heavy Atom Count 22.0
Description Neohesperidoside, also known as 2-O-alpha-L-rhamnopyranosyl-D-glucopyranose or alpha-L-rhap-(1->2)-beta-D-glcp, is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Neohesperidoside is soluble (in water) and a very weakly acidic compound (based on its pKa). Neohesperidoside can be found in lemon, which makes neohesperidoside a potential biomarker for the consumption of this food product. Neohesperidoside is the disaccharide which is present in some flavonoids. It can be found in species of typha, in species of typha angustifolia .
Isotope Atom Count 0.0
Molecular Complexity 368.0
Database Name fooddb_chem_all;hmdb_chem_all;pubchem
Defined Atom Stereocenter Count 10.0
Iupac Name (2S,3R,4R,5R,6S)-2-methyl-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
Nih Violation True
Class Organooxygen compounds
Xlogp -3.7
Superclass Organic oxygen compounds
Is Pains False
Subclass Carbohydrates and carbohydrate conjugates
Molecular Formula C12H22O10
Inchi Key VSRVRBXGIRFARR-OUEGHFHCSA-N
Rotatable Bond Count 3.0
Synonyms 2-O-(alpha-L-Rhamnopyranosyl)-beta-D-glucopyranose, 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose, 6-Deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-glucopyranose, alpha-L-Rhap-(1->2)-beta-D-GLCP, Neohesperidose, 2-O-(a-L-Rhamnopyranosyl)-b-D-glucopyranose, 2-O-(Α-L-rhamnopyranosyl)-β-D-glucopyranose, 2-O-a-L-Rhamnopyranosyl-D-glucopyranose, 2-O-Α-L-rhamnopyranosyl-D-glucopyranose, 6-Deoxy-a-L-mannopyranosyl-(1->2)-b-D-glucopyranose, 6-Deoxy-α-L-mannopyranosyl-(1->2)-β-D-glucopyranose, a-L-Rhap-(1->2)-b-D-GLCP, Α-L-rhap-(1->2)-β-D-GLCP, a-L-Rhamnopyranosyl-(1->2)-b-D-glucopyranose, α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranose
Compound Name 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose
Kingdom Organic compounds
Exact Mass 326.121
Formal Charge 0.0
Brenk Violation False
Monoisotopic Mass 326.121
Hydrogen Bond Acceptor Count 10.0
Molecular Weight 326.3
Covalent Unit Count 1.0
Total Atom Stereocenter Count 10.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aliphatic heteromonocyclic compounds
Inchi InChI=1S/C12H22O10/c1-3-5(14)7(16)9(18)12(20-3)22-10-8(17)6(15)4(2-13)21-11(10)19/h3-19H,2H2,1H3/t3-,4+,5-,6+,7+,8-,9+,10+,11+,12-/m0/s1
Smiles C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O)CO)O)O)O)O)O
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent O-glycosyl compounds

  • 1. Outgoing r'ship FOUND_IN to/from Citrus Limon (Plant) Rel Props:Source_db:fooddb_chem_all