ChemFOnt: Showing chemical card for Phloretin-2'-O-(2''-O-xylosylglucoside) (CFc000281186)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:19 UTC

Chemfont ID

CFc000281186

Molecule Identification

Common Name

Phloretin-2'-O-(2''-O-xylosylglucoside)

Definition

Phloretin-2'-o-(2''-o-xylosylglucoside) is a member of the class of compounds known as flavonoid o-glycosides. Flavonoid o-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phloretin-2'-o-(2''-o-xylosylglucoside) is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Phloretin-2'-o-(2''-o-xylosylglucoside) can be found in apple, apricot, and pear, which makes phloretin-2'-o-(2''-o-xylosylglucoside) a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₄

Average Molecular Weight

568.5239

Monoisotopic Molecular Weight

568.179205732

IUPAC Name

1-(2-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

Traditional Name

1-(2-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

CAS Registry Number

60-82-2

SMILES

OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=CC(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H32O14/c27-9-17-20(33)22(35)24(40-25-23(36)21(34)18(10-28)38-25)26(39-17)37-16-8-13(30)7-15(32)19(16)14(31)6-3-11-1-4-12(29)5-2-11/h1-2,4-5,7-8,17-18,20-30,32-36H,3,6,9-10H2/t17-,18-,20-,21+,22+,23-,24-,25+,26-/m1/s1

InChI Key

ZPVXZDCYCDBKAJ-NCMRLHFPSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Phenolic glycoside
Alkyl-phenylketone
O-glycosyl compound
Glycosyl compound
Butyrophenone
Disaccharide
Phenylketone
Phenol ether
Phenoxy compound
Resorcinol
Benzoyl
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Oxane
Benzenoid
Tetrahydrofuran
Vinylogous acid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301670)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Drupe

Apricot (FooDB: FOOD00144)

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)

Fermented beverage

Apple cider (FooDB: FOOD00615)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.78 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	-0.16	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-3	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	10	ChemAxon
Refractivity	132.3 m³·mol⁻¹	ChemAxon
Polarizability	55.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0301670

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000084

KNApSAcK ID

Not Available

Chemspider ID

59696152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101746085

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Phloretin-2'-O-(2''-O-xylosylglucoside) (CFc000281186)

MOL for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

3D MOL for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

3D SDF for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

3D-SDF for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

PDB for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

3D PDB for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

SMILES for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

INCHI for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

Structure for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))

3D Structure for CFc000281186 (Phloretin-2'-O-(2''-O-xylosylglucoside))