ChemFOnt: Showing chemical card for (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (CFc000281607)

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

CFc000281607

Molecule Identification

Common Name

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

Definition

(2s)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside is a member of the class of 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 (2s)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (2s)-naringenin 8-c-alpha-l-rhamnopyranosyl-(1->2)-beta-d-glucopyranoside can be found in loquat, which makes (2s)-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
(2S)-Naringenin 8-C-a-L-rhamnopyranosyl-(1->2)-b-D-glucopyranoside	Generator
(2S)-Naringenin 8-C-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	Generator

Chemical Formula

C₂₇H₃₂O₁₄

Average Molecular Weight

580.5346

Monoisotopic Molecular Weight

580.179205732

IUPAC Name

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

Traditional Name

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

CAS Registry Number

278614-43-0

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

InChI Identifier

InChI=1S/C27H32O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-6,9,15-16,19-23,25-31,33-37H,7-8H2,1H3/t9-,15-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302091)

Food

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.95 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.65	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.28 m³·mol⁻¹	ChemAxon
Polarizability	55.54 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

HMDB0302091

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001847

KNApSAcK ID

Not Available

Chemspider ID

8778688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10603320

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (CFc000281607)

MOL for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D MOL for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D SDF for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D-SDF for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

PDB for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D PDB for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

SMILES for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

INCHI for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

Structure for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D Structure for CFc000281607 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)