Isorhamnetin (CHEM021808)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:03 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021808
Identification
Common NameIsorhamnetin
ClassSmall Molecule
DescriptionA monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5,7,4'-Tetrahydroxy-3'-methoxyflavoneChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-benzopyran-4-oneChEBI
3-MethylquercetinChEBI
IsorhamnetolChEBI
Quercetin 3'-methyl etherChEBI
3'-Methoxy-3,4',5,7-tetrahydroxyflavoneHMDB
3'-MethoxyquercetinHMDB
3'-MethylquercetinHMDB
3'-O-MethylquercetinHMDB
3,4',5,7-Tetrahydroxy-3'-methoxy-flavoneHMDB, MeSH
3,4',5,7-Tetrahydroxy-3'-methoxyflavoneHMDB, MeSH
3-MethylquercetineHMDB
4'-MethoxyquercetinHMDB
4'-MethylquercetinHMDB
4'-O-MethylquercetinHMDB
3-O-MethylquercetinMeSH, HMDB
iso-RhamnetinMeSH, HMDB
IsorhamnetineMeSH, HMDB
3-Methyl-quercetinMeSH, HMDB
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-onePhytoBank
3,4’,5,7-Tetrahydroxy-3’-methoxyflavonePhytoBank
3’-MethoxyquercetinPhytoBank
3’-MethylquercetinPhytoBank
3’-O-MethylquercetinPhytoBank
Quercetin 3’-methyl etherPhytoBank
Chemical FormulaC16H12O7
Average Molecular Mass316.262 g/mol
Monoisotopic Mass316.058 g/mol
CAS Registry Number480-19-3
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional Nameisorhamnetin
SMILESCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI IdentifierInChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChI KeyIZQSVPBOUDKVDZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.96ALOGPS
logP2.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability30.58 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0591000000-2e1f6e28bf0d47d5e240Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001u-0041090000-7e13d91dc4b2bd93fc17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0394000000-f903b8df9b79e6a94f44Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0956000000-6286c6784746c9eba0e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0219000000-c620190cc3878a4242f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-1941000000-10313269e61a0584f37fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0109000000-082620470bd7fd8a6897Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0491000000-da6ec11ed89cc64a7972Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-141b68c1e564685b35ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-8fa57905e16cdfcc4e9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0493000000-2b88769e97319b5f076cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0udi-1940000000-51e0d426523f81faa98bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0gb9-0009000000-caca1c7784ed9828dfb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-0233e63233dadf52ffc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0zfr-0952000000-13e1d438b3f800cfc18aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0209000000-89d7fc697d82018c1228Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-0209000000-405d086d8e4de2b975b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-1910000000-170b80b866f2075e44e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0029000000-a9da21c499e339f09ac6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0493000000-14bbb49d59d91543a76eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-3458ddb4f7ba64eb81c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-bb7cbcffdd9f296b6b9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0079000000-c73663231834b1b1b79aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-3790000000-3b8ca78684ffcba51bf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-57dd2505d869c8f411dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0169000000-38b50b4081dff638023bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frb-3890000000-3525a3f4676b6a964b71Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002655
FooDB IDFDB000604
Phenol Explorer ID318
KNApSAcK IDC00004635
BiGG IDNot Available
BioCyc IDCPD-8004
METLIN ID3445
PDB IDNot Available
Wikipedia LinkIsorhamnetin
Chemspider ID4444973
ChEBI ID6052
PubChem Compound ID5281654
Kegg Compound IDC10084
YMDB IDYMDB01720
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21948481
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22790928
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23391847
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23417281
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23441850
6. Heap, Tom; Robinson, Robert. Synthesis of kaempferide and of isorhamnetin. Journal of the Chemical Society (1926), 2336-44.
7. Sheu JR, Hsiao G, Chou PH, Shen MY, Chou DS: Mechanisms involved in the antiplatelet activity of rutin, a glycoside of the flavonol quercetin, in human platelets. J Agric Food Chem. 2004 Jul 14;52(14):4414-8.
8. Chanoine JP, Braverman LE: The role of transthyretin in the transport of thyroid hormone to cerebrospinal fluid and brain. Acta Med Austriaca. 1992;19 Suppl 1:25-8.
9. Ritter J, Kahl R, Hildebrandt AG: Effect of the antioxidant (+)-cyanidanol-3 on H2O2 formation and lipid peroxidation in liver microsomes. Res Commun Chem Pathol Pharmacol. 1985 Jan;47(1):48-58.
10. Kandaswami C, Lee LT, Lee PP, Hwang JJ, Ke FC, Huang YT, Lee MT: The antitumor activities of flavonoids. In Vivo. 2005 Sep-Oct;19(5):895-909.
11. Lee HJ, Noh YH, Lee DY, Kim YS, Kim KY, Chung YH, Lee WB, Kim SS: Baicalein attenuates 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells. Eur J Cell Biol. 2005 Nov;84(11):897-905.
12. Chen CY, Milbury PE, Lapsley K, Blumberg JB: Flavonoids from almond skins are bioavailable and act synergistically with vitamins C and E to enhance hamster and human LDL resistance to oxidation. J Nutr. 2005 Jun;135(6):1366-73.
13. Lindahl M, Tagesson C: Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. Inflammation. 1997 Jun;21(3):347-56.
14. Wenisch C, Biffignandi PM: Effect of bioflavonoids (trihydroxyethylrutin and disodium flavodate) in vitro on neutrophil reactive oxygen production and phagocytic ability assessed by flow cytometry. Curr Med Res Opin. 2001;17(2):123-7.
15. Hubbard GP, Wolffram S, Lovegrove JA, Gibbins JM: Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans. J Thromb Haemost. 2004 Dec;2(12):2138-45.
16. Shoab SS, Porter JB, Scurr JH, Coleridge-Smith PD: Effect of oral micronized purified flavonoid fraction treatment on leukocyte adhesion molecule expression in patients with chronic venous disease: a pilot study. J Vasc Surg. 2000 Mar;31(3):456-61.
17. Lu J, Feng X, Sun Q, Lu H, Manabe M, Sugahara K, Ma D, Sagara Y, Kodama H: Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils. Clin Chim Acta. 2002 Feb;316(1-2):95-9.
18. Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C: Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med. 2001 Nov 1;31(9):1139-46.
19. Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG: Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther. 1992 Jun;261(3):1195-9.
20. Engler MB, Engler MM, Chen CY, Malloy MJ, Browne A, Chiu EY, Kwak HK, Milbury P, Paul SM, Blumberg J, Mietus-Snyder ML: Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults. J Am Coll Nutr. 2004 Jun;23(3):197-204.
21. Brusselmans K, Vrolix R, Verhoeven G, Swinnen JV: Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity. J Biol Chem. 2005 Feb 18;280(7):5636-45. Epub 2004 Nov 8.
22. Chen G, Lu H, Wang C, Yamashita K, Manabe M, Meng Z, Xu S, Kodama H: Effect of five flavonoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta. 2002 Dec;326(1-2):169-75.
23. Young JM, Shand BI, McGregor PM, Scott RS, Frampton CM: Comparative effects of enzogenol and vitamin C supplementation versus vitamin C alone on endothelial function and biochemical markers of oxidative stress and inflammation in chronic smokers. Free Radic Res. 2006 Jan;40(1):85-94.
24. Meng Z, Zhou Y, Lu J, Sugahara K, Xu S, Kodama H: Effect of five flavonoid compounds isolated from Quercus dentata Thunb on superoxide generation in human neutrophils and phosphorylation of neutrophil proteins. Clin Chim Acta. 2001 Apr;306(1-2):97-102.
25. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9.
26. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71.
27. Janisch KM, Williamson G, Needs P, Plumb GW: Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. Free Radic Res. 2004 Aug;38(8):877-84.
28. Ma G, Yang C, Qu Y, Wei H, Zhang T, Zhang N: The flavonoid component isorhamnetin in vitro inhibits proliferation and induces apoptosis in Eca-109 cells. Chem Biol Interact. 2007 Apr 25;167(2):153-60. Epub 2007 Feb 20.
29. Sanchez M, Lodi F, Vera R, Villar IC, Cogolludo A, Jimenez R, Moreno L, Romero M, Tamargo J, Perez-Vizcaino F, Duarte J: Quercetin and isorhamnetin prevent endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II in rat aorta. J Nutr. 2007 Apr;137(4):910-5.
30. Bao M, Lou Y: Isorhamnetin prevent endothelial cell injuries from oxidized LDL via activation of p38MAPK. Eur J Pharmacol. 2006 Oct 10;547(1-3):22-30. Epub 2006 Jul 22.