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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 22:25:38 UTC
Update Date2021-10-13 04:48:04 UTC
HMDB IDHMDB0006083
Secondary Accession Numbers
  • HMDB06083
Metabolite Identification
Common NameTroxerutin
DescriptionTroxerutin 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 ).
Structure
Data?1582752373
Synonyms
ValueSource
TrioxyethylrutinHMDB
Vitamin P4HMDB
FlavonoidHMDB
3',4',7-Tri-O-(b-hydroxyethyl)rutosideHMDB
3',4',7-Tris(hydroxyethyl)rutinHMDB
3,5-Dihydroxy-3',4',7-tris(2-hydroxyethoxy)flavone 3-rutinosideHMDB
3-[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside]3,5-dihydroxy-3',4',7-tris(2-hydroxyethoxy)-flavoneHMDB
3-[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-delta-glucopyranoside]3,5-dihydroxy-3',4',7-tris(2-hydroxyethoxy)-flavoneHMDB
Factor p-zymaHMDB
PosorutinHMDB
Rufen-P4HMDB
RuvenHMDB
THRHMDB
TriHERHMDB
Tris(hydroxyethyl)rutinHMDB
Tris(hydroxyethyl)rutosideHMDB
Tris-O-(2-hydroxyethyl)rutinHMDB
Tris-O-(b-hydroxyethyl)rutosideHMDB
TroxerutineHMDB
VastribilHMDB
VeinamitolHMDB
VenitenHMDB
Venoruton P4HMDB
Z 6000HMDB
VenorutinHMDB
Venotrulan troxHMDB
3',4',7-Tris(O-(2- hydroxyethyl))rutinHMDB
Troxerutin-ratiopharmHMDB
OxerutinHMDB
Veno SLHMDB
ParovenHMDB
RelveneHMDB
RhéofluxHMDB
3',4',7-TrihydroxyethylrutinHMDB
TebovenHMDB
Troxérutine mazalHMDB
Veniten retardHMDB
VenorutonHMDB
TroxevenHMDB
Chemical FormulaC33H42O19
Average Molecular Weight742.6752
Monoisotopic Molecular Weight742.232029162
IUPAC Name2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameruven
CAS Registry Number7085-55-4
SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(OCCO)=CC(O)=C4C3=O)C3=CC(OCCO)=C(OCCO)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
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/t14-,21+,23-,24+,26+,27-,28+,29+,32+,33-/m0/s1
InChI KeyIYVFNTXFRYQLRP-VVSTWUKXSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility19300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.43 g/LALOGPS
logP10(-0.55) g/LALOGPS
logP10(-2.5) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Acidic)8.34ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area293.21 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity172.47 m³·mol⁻¹ChemAxon
Polarizability73.12 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TroxerutinC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(OCCO)=CC(O)=C4C3=O)C3=CC(OCCO)=C(OCCO)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5181.9Standard polar33892256
TroxerutinC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(OCCO)=CC(O)=C4C3=O)C3=CC(OCCO)=C(OCCO)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5746.4Standard non polar33892256
TroxerutinC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(OCCO)=CC(O)=C4C3=O)C3=CC(OCCO)=C(OCCO)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O6633.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxerutin GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 10V, Positive-QTOFsplash10-002r-1103914700-9118812e6a139677e7ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 20V, Positive-QTOFsplash10-00kr-1204920000-e1a6fe258249bdf38cca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 40V, Positive-QTOFsplash10-000i-0309413000-18cde334d33eb7397b732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 10V, Negative-QTOFsplash10-009w-3311738900-bc8203f2a87b41de15c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 20V, Negative-QTOFsplash10-01yk-2407319300-d09ced6a80acfeabd4f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 40V, Negative-QTOFsplash10-0019-1309403000-dcb1e6055caa3e58fcf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 10V, Positive-QTOFsplash10-000i-0000900200-67645d791629add48e0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 20V, Positive-QTOFsplash10-000o-0000900900-a2300754ed17d9d7b9912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 40V, Positive-QTOFsplash10-000i-0000900000-8d96ed536fe3359a7ffa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 10V, Negative-QTOFsplash10-0006-0000000900-acfa986c3ddec08dd01a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 20V, Negative-QTOFsplash10-000x-0000500900-7ece5d3b366c14d1584c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxerutin 40V, Negative-QTOFsplash10-001i-0010900100-c1e52788f916928bee372021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13124
Phenol Explorer Compound IDNot Available
FooDB IDFDB001254
KNApSAcK IDNot Available
Chemspider ID4589027
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTroxerutin
METLIN IDNot Available
PubChem Compound5486699
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1804511
References
Synthesis ReferenceCourbat, P.; Uhlmann, G.; Guerne, R. Product of the b-hydroxyethylation of rutoside. II. Identification of the major constituents by ultraviolet spectrophotometry. Helvetica Chimica Acta (1966), 49(4), 1420-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Turner RB, Fowler SL, Berg K: Treatment of the common cold with troxerutin. APMIS. 2004 Sep;112(9):605-11. [PubMed:15601310 ]
  2. Adam BS, Pentz R, Siegers CP, Strubelt O, Tegtmeier M: Troxerutin protects the isolated perfused rat liver from a possible lipid peroxidation by coumarin. Phytomedicine. 2005 Jan;12(1-2):52-61. [PubMed:15693708 ]
  3. Chung HK, Choi SM, Ahn BO, Kwak HH, Kim JH, Kim WB: Efficacy of troxerutin on streptozotocin-induced rat model in the early stage of diabetic retinopathy. Arzneimittelforschung. 2005;55(10):573-80. [PubMed:16294503 ]
  4. Maurya DK, Balakrishnan S, Salvi VP, Nair CK: Protection of cellular DNA from gamma-radiation-induced damages and enhancement in DNA repair by troxerutin. Mol Cell Biochem. 2005 Dec;280(1-2):57-68. [PubMed:16311905 ]