Showing Compound Quercetin 3-[glucosyl-(1->?)-glucuronide] (FDB017823)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:20 UTC

Update date

2019-11-26 03:15:17 UTC

Primary ID

FDB017823

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Quercetin 3-[glucosyl-(1->?)-glucuronide]

Description

Nelumboside belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Nelumboside has been detected, but not quantified in, bilberries (Vaccinium myrtillus) and herbs and spices. This could make nelumboside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Nelumboside.

CAS Number

93252-57-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S,3S,4R,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate	Generator
3,3',4',5,7-Pentahydroxyflavone 3-O-[b-D-glucopyranosyl-(1->?)-b-D-glucuronopyranoside]	manual
Nelumboside	db_source
Quercetin 3-[glucosyl-(1->?)-glucuronide]	manual
Quercetin 3-O-[b-D-glucopyranosyl-(1->?)-b-D-glucuronopyranoside]	manual

Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	8.31 g/L	ALOGPS
logP	0.38	ALOGPS
logP	-1.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	302.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.56 m³·mol⁻¹	ChemAxon
Polarizability	58.71 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	Yes	ChemAxon

Chemical Formula

C27H28O18

IUPAC name

(2S,3S,4R,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C27H28O18/c28-6-13-15(33)17(35)19(37)26(42-13)44-23-18(36)20(38)27(45-24(23)25(39)40)43-22-16(34)14-11(32)4-8(29)5-12(14)41-21(22)7-1-2-9(30)10(31)3-7/h1-5,13,15,17-20,23-24,26-33,35-38H,6H2,(H,39,40)/t13-,15-,17+,18-,19-,20-,23+,24+,26+,27-/m1/s1

InChI Key

RFPZGZUMXXMVEL-UBSYNHCDSA-N

Isomeric SMILES

OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC(O)=C(O)C=C3)O[C@@H]2C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

640.5004

Monoisotopic Molecular Weight

640.127564092

Classification

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Catechol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Pyran
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Acetal
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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 50.63%; H 4.41%; O 44.96%	DFC
Melting Point	Mp 174-175°	DFC
Optical Rotation	[a]26D -21.1 (H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-5834169000-75656b2b7750eab791d6	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-[glucosyl-(1->?)-glucuronide], TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0139808000-6ba2efa4e51ab831c6c5	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0239401000-0c0287d5c5ef9db4ce48	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-1946100000-26399b8c6ae6f82d3cd1	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ug0-1338539000-ccc52586156462573454	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2329411000-9ede8e167a200914fd3b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3936200000-73a9be085bba768cb075	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000009000-70ca1c86ba5b818eb55c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-0005009000-7dc45c262f3d0b5869d2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0019001000-a57d663fc642ed87faa6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009002000-fddfddebb95380f04c7c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udo-0009009000-1005a9f4ba14e392bc47	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0009000000-58b2754f892c40f07699	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

30777256

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

11968794

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38464

CRC / DFC (Dictionary of Food Compounds) ID

ODR86-B:LBF81-T

EAFUS ID

Not Available

Dr. Duke ID

QUERCETIN-3-GLUCOSYL-GLUCOSIDE|QUERCETIN-3-GLUCOSIDOGLUCOSIDE

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

HBR39-C:LBF81-T

Associated Foods

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Food	Content Range	Average	Reference

Bilberry	Expected but not quantified	Not Available	DUKE

Showing 1 to 1 of 1 entries

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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Quercetin 3-[glucosyl-(1->?)-glucuronide] (FDB017823)

Structure for FDB017823 (Quercetin 3-[glucosyl-(1->?)-glucuronide])