Showing Compound 6-Hydroxyluteolin 7-rhamnoside (FDB021743)

Record Information

Version

1.0

Creation date

2011-03-17 23:28:39 UTC

Update date

2019-11-26 03:20:50 UTC

Primary ID

FDB021743

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6-Hydroxyluteolin 7-rhamnoside

Description

6-hydroxyluteolin 7-rhamnoside 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. 6-hydroxyluteolin 7-rhamnoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 6-hydroxyluteolin 7-rhamnoside can be found in mexican oregano, which makes 6-hydroxyluteolin 7-rhamnoside a potential biomarker for the consumption of this food product.

CAS Number

107390-48-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3',4',5,6,7-Pentahydroxyflavone 7-O-a-L-rhamnopyranoside	manual
6-Hydroxyluteolin 7-O-a-L-rhamnopyranoside	manual
6-Hydroxyluteolin 7-O-a-L-rhamnoside	manual
6-Hydroxyluteolin 7-O-rhamnoside	manual
6-Hydroxyluteolin 7-rhamnoside	manual

Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.41 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.88	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.41	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.48 m³·mol⁻¹	ChemAxon
Polarizability	43.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O11

IUPAC name

2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one

InChI Identifier

InChI=1S/C21H20O11/c1-7-16(25)19(28)20(29)21(30-7)32-14-6-13-15(18(27)17(14)26)11(24)5-12(31-13)8-2-3-9(22)10(23)4-8/h2-7,16,19-23,25-29H,1H3

InChI Key

WBSLGYBCKVSSQR-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OC2=CC3=C(C(=O)C=C(O3)C3=CC(O)=C(O)C=C3)C(O)=C2O)C(O)C(O)C1O

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

Classification

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
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 56.25%; H 4.50%; O 39.25%	DFC
Melting Point	Mp 266? (as hepta-Ac)	DFC
Optical Rotation	[a]25D -60.1 (c, 0.32 in CHCl3) (hepta-Ac)	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	splash10-0udj-0149800000-b931c0794eabf4d868b0	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0289100000-8bd36064124a9fe9b495	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-2792000000-a8963ac223d43d87d5ae	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-2207900000-5bd61a0b914343a368d0	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2249200000-2147f69823ddc7a1a4e9	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfu-5494000000-728528a0400fb3d1bccc	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-6cdaf2bc31caca882f1d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000900000-6cdaf2bc31caca882f1d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0419700000-8e0c9ce644e3bc61f1ba	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-e34b057bc120eef7d6a0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000900000-578e80e06a8f791630d8	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0955400000-d57d92c5c589d52431dc	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

279

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

KDD85-Q:LHZ69-H

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 6-Hydroxyluteolin 7-rhamnoside (FDB021743)

Structure for FDB021743 (6-Hydroxyluteolin 7-rhamnoside)