Showing Compound Quercetin 3-alpha-D-galactoside (FDB021640)

Record Information

Version

1.0

Creation date

2011-03-17 23:25:22 UTC

Update date

2020-02-24 19:11:05 UTC

Primary ID

FDB021640

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Quercetin 3-alpha-D-galactoside

Description

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4h-chromen-4-one is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4h-chromen-4-one can be found in a number of food items such as red raspberry, german camomile, caraway, and bilberry, which makes 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4h-chromen-4-one a potential biomarker for the consumption of these food products.

CAS Number

65549-68-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	MeSH, HMDB
3,3',4',5,7-Pentahydroxyflavone 3-O-a-D-galactopyranoside	manual
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy	MeSH, HMDB
Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside	MeSH, HMDB
Isohyperoside?	db_source
Isoquercetin	MeSH, HMDB
Isoquercitin	MeSH, HMDB
Isoquercitroside	MeSH, HMDB
Isotrifoliin	MeSH, HMDB
Quercetin 3-(beta-D-glucofuranoside)	MeSH, HMDB

Showing 1 to 10 of 22 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.95 g/L	ALOGPS
logP	0.47	ALOGPS
logP	-0.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.28 m³·mol⁻¹	ChemAxon
Polarizability	43.39 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

C21H20O12

IUPAC name

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

InChI Identifier

InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2

InChI Key

OVSQVDMCBVZWGM-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O

Average Molecular Weight

464.3763

Monoisotopic Molecular Weight

464.095476104

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

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 54.32%; H 4.34%; O 41.34%	DFC
Melting Point	Mp 242-245?	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014r-3620009000-aa92fb234d45c04fb4a1	Spectrum
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uea-8903800000-39e954868a814e35f210	Spectrum
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Quercetin 3-alpha-D-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-0049500000-20e4fa8431a412ba6e72	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-0udi-0049400000-57f0e54fd0a63993ec29	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-0049600000-97fd2ad1db1430a06040	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0159000000-cbdc9506eda9b72e273b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0009000000-8d0c97d5f4b72edf6907	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-0049500000-06bb5b7c561f318ccd7c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0169000000-4b074a7221cb7ddc3ab7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-0w29-0029800000-8cdd2547cd9e683a4299	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0290000000-83b6bb1fcc715c093d03	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-0029800000-29a463f7205be78952db	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0049400000-21f606dc00e0fa8b1489	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03di-0002900000-ec5593251ed9c77f2e27	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-0049500000-e10c29f517c285f60e3f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0390000000-c5faddda80502a2e9dfd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03di-0002900000-5715cf05e3136d0d9893	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0290000000-e2e8be47ff4b35f3d50f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0159000000-a8efaae63da17e22db76	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0159000000-7270b42009be0e90b6f8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03di-0002900000-d1f60685296b1015259e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0128900000-322729b83b9a5a6c77be	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0289100000-1d31df3055902067f16a	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fki-1963000000-0bafbbfdc4b8c66e92d0	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-0205900000-e3b73a70dbcdc676fe63	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1449300000-d44433eb2305d966c28b	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdi-3932000000-c3c8f57f573b48beacf6	2019-02-23	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

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HBR39-C:KWD87-V

EAFUS ID

Not Available

Dr. Duke ID

QUERCETIN-3-O-BETA-D-GALACTOSIDE|QUERCETIN-3-0-GALACTOSIDE

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

Bilberry	Expected but not quantified	Not Available	DUKE
Black tea	Expected but not quantified	Not Available	DUKE
Caraway	Expected but not quantified	Not Available	DUKE
German camomile	Expected but not quantified	Not Available	DUKE
Green tea	Expected but not quantified	Not Available	DUKE
Herbal tea	Expected but not quantified	Not Available	DUKE
Peach	Expected but not quantified	Not Available	DUKE
Pear	Expected but not quantified	Not Available	DUKE
Red raspberry	Expected but not quantified	Not Available	DUKE
Red tea	Expected but not quantified	Not Available	DUKE