Showing Compound Luteolin 7-glucoside (FDB014280)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:11 UTC

Update date

2020-09-17 15:32:55 UTC

Primary ID

FDB014280

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Luteolin 7-glucoside

Description

Luteolin-7-O-glucoside, also known as 7-O-glucoluteolin or cinaroside, belongs to the class of organic compounds known as flavonoid O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. glucoside. Because of the conjugation of glucose, Luteolin 7-O-glucoside is a moderately water-soluble compound. Luteolin 7-O-glucoside is found, on average, in a few different plants, spices and foods, such as Mexican oregano, anises, and wild celeries and in a lower concentration in lentils, and wild carrots. common buckwheats, corns, globe artichokes, roman camomiles, and orange mints.

CAS Number

5373-11-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside	ChEBI
2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	ChEBI
7-Glucoluteolin	ChEBI
7-Glucosylluteolin	ChEBI
7-O-beta-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone	ChEBI
Cinaroside	ChEBI
Cynaroside	ChEBI
Luteolin 7-monoglucoside	ChEBI
Luteolin 7-O-glucopyranoside	ChEBI
Luteolin 7-O-glucoside	ChEBI
Luteolin-7-glucoside	ChEBI
Luteoloside	ChEBI
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl b-D-glucopyranoside	Generator
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside	Generator
2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	Generator
7-O-b-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone	Generator
7-O-Β-D-glucosyl-5,7,3',4'-tetrahydroxyflavone	Generator
Luteolin 7-glucoside	ChEBI
Daphneflavonoloside	HMDB
Flavopurposide	HMDB
Glucoluteolin	HMDB
Luteolin 7-O-beta-D-glucoside	HMDB
Luteolin 7-O-b-D-glucoside	Generator
Luteolin 7-O-β-D-glucoside	Generator
Nephrocizin	MeSH
Luteolin-7-O-monoglucoside	MeSH
Luteolin-7-O-beta-D-glucopyranoside	MeSH
Luteolin-7-beta-D-glucoside	MeSH
3',4',5,7-Tetrahydroxyflavone 7-beta-D-glucopyranoside	PhytoBank
3',4',5,7-Tetrahydroxyflavone 7-β-D-glucopyranoside	PhytoBank
3’,4’,5,7-Tetrahydroxyflavone 7-β-D-glucopyranoside	PhytoBank
3',4',5-Trihydroxyflavone 7-O-beta-D-glucopyranoside	PhytoBank
3',4',5-Trihydroxyflavone 7-O-β-D-glucopyranoside	PhytoBank
3’,4’,5-Trihydroxyflavone 7-O-β-D-glucopyranoside	PhytoBank
7-(beta-D-Glucosyloxy)-3',4',5-trihydroxyflavone	PhytoBank
7-(β-D-Glucosyloxy)-3',4',5-trihydroxyflavone	PhytoBank
7-(β-D-Glucosyloxy)-3’,4’,5-trihydroxyflavone	PhytoBank
7-O-beta-D-Glucosylluteolin	PhytoBank
7-O-β-D-Glucosylluteolin	PhytoBank
Luteolin 7-O-beta-D-glucopyranoside	PhytoBank
Luteolin 7-O-β-D-glucopyranoside	PhytoBank
Luteolin 7-O-beta-glucopyranoside	PhytoBank
Luteolin 7-O-β-glucopyranoside	PhytoBank
Luteolin 7-O-beta-glucoside	PhytoBank
Luteolin 7-O-β-glucoside	PhytoBank
Luteolin 7-beta-D-glucoside	PhytoBank
Luteolin 7-β-D-glucoside	PhytoBank
7-O-β-D-glucosyl-5,7,3',4'-tetrahydroxyflavone	Generator

Predicted Properties

Property	Value	Source
Water Solubility	1.08 g/L	ALOGPS
logP	0.58	ALOGPS
logP	0.14	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3	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	4	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	42.98 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-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

InChI Key

PEFNSGRTCBGNAN-QNDFHXLGSA-N

Isomeric SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

Classification

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:27994 )
monosaccharide derivative (CHEBI:27994 )
glycosyloxyflavone (CHEBI:27994 )
trihydroxyflavone (CHEBI:27994 )
flavones (C03951 )
Flavones and Flavonols (C03951 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 56.25%; H 4.50%; O 39.25%	DFC
Melting Point	Mp 256-258° (254°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	398 (e 21000) (MeOH-NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Luteolin 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001r-8934600000-7e7c6044b90fb9c11463	Spectrum
Predicted GC-MS	Luteolin 7-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f72-4730119000-f82ba729f371b8abdbda	Spectrum
Predicted GC-MS	Luteolin 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0010900030-c10d893db863fa97d0a8	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0010900030-c10d893db863fa97d0a8	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-000i-0090000000-f076599705f9f223d360	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-000i-0090100000-fe6850abbcec4fe56dd9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0012-0190500000-bcf45c556204b1713d58	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0030900020-65868b413ea8969c4672	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0019-0090000000-0908e4e690a4acb6edfc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0000900000-f15806fb1fd62f75af54	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001a-0190400000-862638c136c541fb742b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0091000000-f63c0d3cebcf6fc2e507	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-0040900000-e3f9043e8fac7872cb66	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-1ff8e42522b8a1f6961a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090100000-cb0df3f467ea51e6ab18	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000j-0090600000-8f1dad507334d836e2a8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0190000000-e3aa1461dda1c7043d2d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF , positive	splash10-000i-0090000000-31bb8bd03bfd2eff538b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0091100000-ea4c2b653cea6f474766	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0090000000-8392154e4309f46037d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-0090000000-a15f658ade963370f0c3	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0190600000-49dfd37238ba14bc6c11	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0190000000-8733c538660a8dd11d05	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1390000000-ceeece13914238abed46	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-1261900000-e1ec4112e692ec8fbbd6	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1190100000-bcbf2a30e128889e8047	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-2190000000-954ea2eef82d3bedfb36	2016-08-04	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

245

DrugBank ID

Not Available

HMDB ID

HMDB35588

CRC / DFC (Dictionary of Food Compounds) ID

HQG45-Z:JPC55-X

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

Not Available

KNApSAcK ID

C00004266

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

Luteolin_7-glucoside

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti complementary		A substance that diminishes or abolishes the action of a complement, playing a role in regulating the immune system. Therapeutically, it's used to prevent excessive inflammation and tissue damage. Key medical uses include treating autoimmune disorders, transplant rejection, and inflammatory diseases.	DUKE
Anti dermatic	50177	An agent that reduces skin inflammation and allergic reactions, commonly used in managing dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and irritation.	DUKE
Anti-herpetic	22587	An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.	DUKE
Anti hyperthyroid	52217	An agent that reduces thyroid hormone production, used to manage hyperthyroidism by decreasing thyroid-stimulating hormone (TSH) and thyroid hormone levels, commonly used to treat conditions such as Graves' disease and thyroid storm.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Calcium antagonist	48706	A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Cholagogue		An agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.	DUKE
Deiodinase inhibitor	23924	An agent that blocks the activity of deiodinases, enzymes involved in thyroid hormone regulation. It reduces thyroid hormone conversion, commonly used in managing thyroid disorders, such as hyperthyroidism, and certain types of cancer, including thyroid cancer.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Insectiphile	24852	A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE