Showing Compound Troxerutin (FDB001254)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:53 UTC

Update date

2018-05-28 23:05:34 UTC

Primary ID

FDB001254

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Troxerutin

Description

Bioflavonoid Troxerutin is a flavonol, a type of flavonoid. It is more acurately a hydroxyethylrutoside. It can be isolated from Sophora japonica, the japanese pagoda tree.; Troxerutin is a rutoside, a naturally occurring flavonoid. Flavonoids are polyphenolic compounds that are present in most fruits and vegetables. Although flavonoids are devoid of classical nutritional value, they are increasingly viewed as beneficial dietary components that act as potential protectors against human diseases such as coronary heart disease, cancers, and inflammatory bowel disease. Troxerutin is a beneficial cofactor in coumarin preparations used for the therapy of chronic venous insufficiency, since has hepatoprotective properties and thus protects the liver from a possible lipid peroxidation caused by coumarin. Oxidative stress might be involved in the upregulation of retinal vascular endothelial growth factor (VEGF) during early diabetes, and it is likely that troxerutin has comparatively effective antioxidant properties; therefore, troxerutin might be a useful treatment for attenuating diabetic retinopathy. Troxerutin offers protection against gamma-radiation-induced micronuclei formation and DNA strand breaks and enhances repair of radiation-induced DNA strand breaks, in addition to anti-erythrocytic, anti-thrombic, fibrinolytic and oedema-protective rheological activity. (PMID: 15601310, 15693708, 16294503, 16311905).

CAS Number

7085-55-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-[3,4-Bis(2-hydroxyethoxy)phenyl]-3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-7-(2-hydroxyethoxy)-4H-1-benzopyran-4-one, 9CI	db_source
3',4',7-Tri-O-(b-hydroxyethyl)rutoside	biospider
3',4',7-Trihydroxyethylrutin	MeSH
3',4',7-Tris(hydroxyethyl)rutin	biospider
3',4',7-Tris(O-(2- hydroxyethyl))rutin	MeSH
3',4',7-Tris[O-(2-hydroxyethyl)]rutin	biospider
3,5-Dihydroxy-3',4',7-tris(2-hydroxyethoxy)flavone 3-[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside], 8CI	db_source
Factor p-zyma	biospider
Oxerutin	MeSH
Paroven	MeSH

Showing 1 to 10 of 38 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.43 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-2.5	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	293.21 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	172.47 m³·mol⁻¹	ChemAxon
Polarizability	73.84 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

C33H42O19

IUPAC name

2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one

InChI Identifier

InChI=1S/C33H42O19/c1-14-23(38)26(41)28(43)32(49-14)48-13-21-24(39)27(42)29(44)33(51-21)52-31-25(40)22-17(37)11-16(45-7-4-34)12-20(22)50-30(31)15-2-3-18(46-8-5-35)19(10-15)47-9-6-36/h2-3,10-12,14,21,23-24,26-29,32-39,41-44H,4-9,13H2,1H3

InChI Key

IYVFNTXFRYQLRP-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OCC2OC(OC3=C(OC4=C(C(O)=CC(OCCO)=C4)C3=O)C3=CC(OCCO)=C(OCCO)C=C3)C(O)C(O)C2O)C(O)C(O)C1O

Average Molecular Weight

742.6752

Monoisotopic Molecular Weight

742.232029162

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
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
Disaccharide
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Oxane
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
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 53.37%; H 5.70%; O 40.93%	DFC
Melting Point	Mp 181°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5486699

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06083

CRC / DFC (Dictionary of Food Compounds) ID

BXK52-C:BXK52-C

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

Troxerutin

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

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Troxerutin (FDB001254)

Structure for FDB001254 (Troxerutin)