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Human Metabolome Database Version 3.5

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Showing metabocard for Isorhamnetin (HMDB02655)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:01 -0600
Update Date 2013-02-08 17:12:02 -0700
HMDB ID HMDB02655
Secondary Accession Numbers None
Metabolite Identification
Common Name Isorhamnetin
Description Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells. (PMID: 15493462 Link_out, 17368593 Link_out, 17374653 Link_out, 16963021 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3'-Methoxy-3,4',5,7-tetrahydroxyflavone
  2. 3'-Methoxyquercetin
  3. 3'-Methylquercetin
  4. 3'-O-Methylquercetin
  5. 3,4',5,7-Tetrahydroxy-3'-methoxy-Flavone
  6. 3,4',5,7-Tetrahydroxy-3'-methoxyflavone
  7. 3-Methylquercetin
  8. 3-Methylquercetine
  9. 4'-Methoxyquercetin
  10. 4'-Methylquercetin
  11. 4'-O-Methylquercetin
  12. Isorhamnetol
  13. Quercetin 3'-methyl ether
Chemical Formula C16H12O7
Average Molecular Weight 316.2623
Monoisotopic Molecular Weight 316.058302738
IUPAC Name 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional IUPAC Name isorhamnetin
CAS Registry Number 480-19-3
SMILES COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier InChI=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 Key IZQSVPBOUDKVDZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Flavonoids
Sub Class Flavones
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Flavones and Flavonols(KEGG)
  • Flavones and Flavonols(Lipidmaps)
  • Flavonols(KEGG)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Benzopyran
  • Chromone
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
  • Pyran
  • Pyranone
  • Resorcinol
Direct Parent Flavonols
Ontology
Status Detected and Quantified
Origin
  • Plant
Biofunction
  • RNA component
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 311 - 314 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.15 g/L ALOGPS
LogP 1.96 ALOGPS
LogP 2.3 ChemAxon
LogS -3.33 ALOGPS
pKa (strongest acidic) 6.44 ChemAxon
pKa (strongest basic) -4 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 116.45 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 81.34 ChemAxon
Polarizability 30.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Liver
  • Prostate
  • Platelet
  • Neutrophil
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.043 (0.040-0.046) uM Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
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30 umol/mmol creatinine Adult (>18 years old) Both Normal 24 hours after the 2-day diet started
Urine Detected and Quantified
Article_icon
30 umol/mmol creatinine Adult (>18 years old) Both Normal After 2-day diet protocol
Urine Detected and Quantified
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0.0065 +/- 0.0065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.019 +/- 0.0065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 318 Not Available
Urine Expected and not Quantified
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Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 318 Not Available
Urine Expected and not Quantified
Article_icon
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 318 Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID 318 Link_out
Phenol Explorer Metabolite ID 318 Link_out
FoodDB ID FDB000604
KNApSAcK ID C00004635 Link_out
Chemspider ID 4444973 Link_out
KEGG Compound ID C10084 Link_out
BioCyc ID CPD-8004 Link_out
BiGG ID Not Available
Wikipedia Link Flavonoid Link_out
NuGOwiki Link HMDB02655 Link_out
Metagene Link HMDB02655 Link_out
METLIN ID 3445 Link_out
PubChem Compound 5281654 Link_out
PDB ID Not Available
ChEBI ID 448850 Link_out
References
Synthesis Reference Heap, Tom; Robinson, Robert. Synthesis of kaempferide and of isorhamnetin. Journal of the Chemical Society (1926), 2336-44.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 15237945 Link_out
  2. 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. Pubmed: 1519447 Link_out
  3. 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. Pubmed: 3983470 Link_out
  4. Kanadaswami 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. Pubmed: 16097445 Link_out
  5. 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. Pubmed: 16323286 Link_out
  6. 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. Pubmed: 15930439 Link_out
  7. 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. Pubmed: 9246576 Link_out
  8. 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. Pubmed: 11759181 Link_out
  9. 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. Pubmed: 15613018 Link_out
  10. 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. Pubmed: 10709057 Link_out
  11. 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. Pubmed: 11750278 Link_out
  12. 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. Pubmed: 11677047 Link_out
  13. 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. Pubmed: 1602384 Link_out
  14. 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. Pubmed: 15190043 Link_out
  15. 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. Pubmed: 15533929 Link_out
  16. 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. Pubmed: 12417109 Link_out
  17. 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. Pubmed: 16298763 Link_out
  18. 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. Pubmed: 11282099 Link_out
  19. 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. Pubmed: 16197573 Link_out
  20. 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. Pubmed: 12787887 Link_out