Showing Compound Rhoifolin 4-glucoside (FDB021744)

Record Information

Version

1.0

Creation date

2011-03-17 23:28:41 UTC

Update date

2019-11-26 03:20:50 UTC

Primary ID

FDB021744

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Rhoifolin 4-glucoside

Description

Rhoifolin 4-glucoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Rhoifolin 4-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Rhoifolin 4-glucoside can be found in grapefruit/pummelo hybrid, which makes rhoifolin 4-glucoside a potential biomarker for the consumption of this food product.

CAS Number

31498-83-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4',5,7-Trihydroxyflavone; 7-O-[a-L-Rhamnopyranosyl-(1->2)-b-D-glucopyranoside], 4'-O-b-D-glucopyranoside	db_source
Apigenin 7-neohesperidoside 4'-glucoside	db_source
Rhoifolin 4-glucoside	manual
Rhoifolin 4-O-glucoside	db_source

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	4.04 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	-2.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	304.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	168.07 m³·mol⁻¹	ChemAxon
Polarizability	71.72 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C33H40O19

IUPAC name

7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C33H40O19/c1-11-22(38)25(41)28(44)31(46-11)52-30-27(43)24(40)20(10-35)51-33(30)48-14-6-15(36)21-16(37)8-17(49-18(21)7-14)12-2-4-13(5-3-12)47-32-29(45)26(42)23(39)19(9-34)50-32/h2-8,11,19-20,22-36,38-45H,9-10H2,1H3

InChI Key

PTKZEWKSNFRXLZ-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(OC3OC(CO)C(O)C(O)C3O)C=C2)C(O)C(O)C1O

Average Molecular Weight

740.6593

Monoisotopic Molecular Weight

740.216379098

Classification

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
Pentose monosaccharide
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Tetrahydrofuran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 53.51%; H 5.44%; O 41.04%	DFC
Melting Point	Mp 212-214?	DFC
Optical Rotation	[a]23D -98.5 (c, 1.12 in Py)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00w9-0200980400-025df543bd98db9c9086	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0220930000-10de1138086ecbeb75df	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1410910000-6c9d4f196562f800f958	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01z0-3501890700-00c33512e715cdfbdf57	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-2700960200-336ff9e0398c3eebdb6a	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-7821900000-496909b34413a0b1c5c9	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-0000900400-ca33f819c34fb6c325d3	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001k-0000990100-0efc197e40973d40ca50	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000900000-509ee28ef47ce2bd195a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000010900-2dffc81f822bbaad5181	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001c-0000570900-8771c525009ffbc79cce	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0000900100-fa1bfddbf6d9aad67375	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

288

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CNR54-G:LMW85-D

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound Rhoifolin 4-glucoside (FDB021744)

Structure for FDB021744 (Rhoifolin 4-glucoside)