ChemFOnt: Showing chemical card for (2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (CFc000281606)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:10 UTC

Chemfont ID

CFc000281606

Molecule Identification

Common Name

(2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside

Definition

(2r)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside is soluble (in water) and a very weakly acidic compound (based on its pKa). (2r)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside can be found in loquat, which makes (2r)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-Naringenin 8-C-a-L-rhamnopyranosyl-(1->2)-b-D-glucopyranoside	Generator
(2R)-Naringenin 8-C-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	Generator

Chemical Formula

C₂₆H₃₀O₁₅

Average Molecular Weight

582.5074

Monoisotopic Molecular Weight

582.15847029

IUPAC Name

(2R)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,4R,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,4R,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

278614-44-1

SMILES

[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C(O)C3=C2O[C@H](CC3=O)C2=CC=C(O)C=C2)O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H30O15/c27-7-14-17(32)19(34)24(40-26-21(36)18(33)20(35)25(37)41-26)23(39-14)16-11(30)5-10(29)15-12(31)6-13(38-22(15)16)8-1-3-9(28)4-2-8/h1-5,13-14,17-21,23-30,32-37H,6-7H2/t13-,14-,17-,18-,19+,20-,21-,23+,24-,25-,26-/m1/s1

InChI Key

RSOASCRBGDBQFY-VCLDZDMQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavan
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
C-glycosyl compound
Chromane
1-benzopyran
Benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Vinylogous acid
Ketone
Hemiacetal
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302090)

Food

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	13.6 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-1.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.89 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302090

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001846

KNApSAcK ID

Not Available

Chemspider ID

59696280

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (CFc000281606)

MOL for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D MOL for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D SDF for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D-SDF for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

PDB for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D PDB for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

SMILES for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

INCHI for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

Structure for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D Structure for CFc000281606 ((2R)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)