ChemFOnt: Showing chemical card for Neohesperidoside (CFc000282056)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:03 UTC

Chemfont ID

CFc000282056

Molecule Identification

Common Name

Neohesperidoside

Definition

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 .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-O-(alpha-L-Rhamnopyranosyl)-beta-D-glucopyranose	ChEBI
2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose	ChEBI
6-Deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-glucopyranose	ChEBI
alpha-L-Rhap-(1->2)-beta-D-GLCP	ChEBI
Neohesperidose	ChEBI
2-O-(a-L-Rhamnopyranosyl)-b-D-glucopyranose	Generator
2-O-(Α-L-rhamnopyranosyl)-β-D-glucopyranose	Generator
2-O-a-L-Rhamnopyranosyl-D-glucopyranose	Generator
2-O-Α-L-rhamnopyranosyl-D-glucopyranose	Generator
6-Deoxy-a-L-mannopyranosyl-(1->2)-b-D-glucopyranose	Generator
6-Deoxy-α-L-mannopyranosyl-(1->2)-β-D-glucopyranose	Generator
a-L-Rhap-(1->2)-b-D-GLCP	Generator
Α-L-rhap-(1->2)-β-D-GLCP	Generator
a-L-Rhamnopyranosyl-(1->2)-b-D-glucopyranose	Generator
Α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranose	Generator

Chemical Formula

C₁₂H₂₂O₁₀

Average Molecular Weight

326.298

Monoisotopic Molecular Weight

326.121296908

IUPAC Name

(2S,3R,4R,5R,6S)-2-methyl-6-{[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol

Traditional Name

neohesperidose

CAS Registry Number

17074-02-1

SMILES

[H][C@@]1(C)O[C@@]([H])(O[C@@]2([H])[C@]([H])(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

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

InChI Key

VSRVRBXGIRFARR-OUEGHFHCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

disaccharide (CHEBI:73992 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302540)

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	486 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.7	ChemAxon
logS	0.17	ALOGPS
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.79 m³·mol⁻¹	ChemAxon
Polarizability	30.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon