ChemFOnt: Showing chemical card for Luteolin 7-rhamnosylglucoside (CFc000336876)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:16 UTC

Chemfont ID

CFc000336876

Molecule Identification

Common Name

Luteolin 7-rhamnosylglucoside

Definition

Luteolin, also known as 3',4',5,7-tetrahydroxyflavone or digitoflavone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, luteolin is considered to be a flavonoid lipid molecule. Luteolin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Luteolin is a bitter tasting compound and can be found in a number of food items such as chinese chestnut, horned melon, walnut, and cherry tomato, which makes luteolin a potential biomarker for the consumption of these food products. Luteolin can be found primarily in blood. Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
3',4',5,7-Tetrahydroxyflavone	ChEBI
5,7,3',4'-Tetrahydroxyflavone	ChEBI
Digitoflavone	ChEBI
Flacitran	ChEBI
Luteolol	ChEBI
Salifazide	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one	HMDB
Luteoline	MeSH, HMDB
3',4',5,7-Tetrahydroxy-flavone	MeSH, HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one	PhytoBank
3’,4’,5,7-Tetrahydroxyflavone	PhytoBank
5,7,3’,4’-Tetrahydroxyflavone	PhytoBank
Cyanidenon	PhytoBank

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

luteolin

CAS Registry Number

36473-51-5

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H

InChI Key

IQPNAANSBPBGFQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:15864 )
3'-hydroxyflavonoid (CHEBI:15864 )
flavones (C01514 )
Flavones and Flavonols (C01514 )
Flavones and Flavonols (LMPK12110006 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0005800)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Tropical fruit

Kiwi (FooDB: FOOD00004)

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)

Berry

Strawberry (FooDB: FOOD00083)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Fruit vegetable

Olive (FooDB: FOOD00121)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)
German camomile (FooDB: FOOD00107)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.89 m³·mol⁻¹	ChemAxon
Polarizability	27.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon