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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:01 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002655
Secondary Accession Numbers
  • HMDB02655
Metabolite Identification
Common NameIsorhamnetin
DescriptionIsorhamnetin 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 , 17368593 , 17374653 , 16963021 ).
Structure
Data?1582752253
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 Weight316.2623
Monoisotopic Molecular Weight316.058302738
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional Nameisorhamnetin
CAS Registry Number480-19-3
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 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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point311 - 314 °CNot Available
Boiling Point599.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1122 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.760 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker174.630932474
[M+H]+Baker172.95830932474
[M-H]-Not Available174.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00001936
[M+H]+Not Available172.958http://allccs.zhulab.cn/database/detail?ID=AllCCS00001936
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+174.17430932474
DeepCCS[M-H]-171.81630932474
DeepCCS[M-2H]-205.5530932474
DeepCCS[M+Na]+180.77730932474
AllCCS[M+H]+171.632859911
AllCCS[M+H-H2O]+168.032859911
AllCCS[M+NH4]+175.032859911
AllCCS[M+Na]+175.932859911
AllCCS[M-H]-171.132859911
AllCCS[M+Na-2H]-170.532859911
AllCCS[M+HCOO]-170.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsorhamnetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O15088.9Standard polar33892256
IsorhamnetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O13146.5Standard non polar33892256
IsorhamnetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O13216.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isorhamnetin,1TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3248.4Semi standard non polar33892256
Isorhamnetin,1TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O3225.5Semi standard non polar33892256
Isorhamnetin,1TMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O3259.6Semi standard non polar33892256
Isorhamnetin,1TMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3311.4Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3185.4Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3138.4Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3116.3Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3146.7Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O3117.3Semi standard non polar33892256
Isorhamnetin,2TMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3248.7Semi standard non polar33892256
Isorhamnetin,3TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3136.9Semi standard non polar33892256
Isorhamnetin,3TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3059.1Semi standard non polar33892256
Isorhamnetin,3TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3033.4Semi standard non polar33892256
Isorhamnetin,3TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3139.4Semi standard non polar33892256
Isorhamnetin,4TMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3129.8Semi standard non polar33892256
Isorhamnetin,1TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3524.5Semi standard non polar33892256
Isorhamnetin,1TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O3527.1Semi standard non polar33892256
Isorhamnetin,1TBDMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O3534.1Semi standard non polar33892256
Isorhamnetin,1TBDMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3580.7Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3724.7Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3678.6Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3658.8Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3696.5Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O3661.8Semi standard non polar33892256
Isorhamnetin,2TBDMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3766.6Semi standard non polar33892256
Isorhamnetin,3TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3917.0Semi standard non polar33892256
Isorhamnetin,3TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3820.8Semi standard non polar33892256
Isorhamnetin,3TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3791.0Semi standard non polar33892256
Isorhamnetin,3TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3893.1Semi standard non polar33892256
Isorhamnetin,4TBDMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4022.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isorhamnetin EI-B (Non-derivatized)splash10-014i-2219000000-20feeef38553ee7cdd292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isorhamnetin EI-B (Non-derivatized)splash10-014i-2219000000-20feeef38553ee7cdd292018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorhamnetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0591000000-2e1f6e28bf0d47d5e2402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorhamnetin GC-MS (4 TMS) - 70eV, Positivesplash10-001u-0041090000-7e13d91dc4b2bd93fc172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorhamnetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin DI-ESI-qTof , Positive-QTOFsplash10-0udi-0394000000-f903b8df9b79e6a94f442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin DI-ESI-qTof , Negative-QTOFsplash10-0udi-0956000000-6286c6784746c9eba0e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOFsplash10-0gb9-0219000000-c620190cc3878a4242f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOFsplash10-0zfr-1941000000-10313269e61a0584f37f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOFsplash10-0gb9-0109000000-082620470bd7fd8a68972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOFsplash10-0ufr-0491000000-da6ec11ed89cc64a79722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOFsplash10-014i-0139000000-141b68c1e564685b35ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOFsplash10-014i-0139000000-8fa57905e16cdfcc4e9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 30V, Positive-QTOFsplash10-0udi-0493000000-2b88769e97319b5f076c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 50V, Positive-QTOFsplash10-0udi-1940000000-51e0d426523f81faa98b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 35V, Negative-QTOFsplash10-0gb9-0009000000-caca1c7784ed9828dfb42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOFsplash10-014i-0009000000-0233e63233dadf52ffc52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 30V, Negative-QTOFsplash10-0zfr-0952000000-13e1d438b3f800cfc18a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOFsplash10-0gb9-0209000000-89d7fc697d82018c12282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOFsplash10-0gb9-0209000000-405d086d8e4de2b975b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 50V, Negative-QTOFsplash10-0a4i-1910000000-170b80b866f2075e44e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOFsplash10-014i-0029000000-a9da21c499e339f09ac62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOFsplash10-0udi-0493000000-14bbb49d59d91543a76e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorhamnetin 10V, Positive-QTOFsplash10-014i-0029000000-3458ddb4f7ba64eb81c82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 10V, Positive-QTOFsplash10-014i-0019000000-bb7cbcffdd9f296b6b9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 20V, Positive-QTOFsplash10-014i-0079000000-c73663231834b1b1b79a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 40V, Positive-QTOFsplash10-0uds-3790000000-3b8ca78684ffcba51bf12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOFsplash10-014i-0009000000-57dd2505d869c8f411dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 20V, Negative-QTOFsplash10-014i-0169000000-38b50b4081dff638023b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorhamnetin 40V, Negative-QTOFsplash10-0frb-3890000000-3525a3f4676b6a964b712016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
  • Intestine
  • Leukocyte
  • Liver
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0388 +/- 0.0454 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0399 +/- 0.0450 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.043 (0.040-0.046) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0-0.157 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00432 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0300 +/- 0.0300 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0333 +/- 0.0333 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.02 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.02 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0065 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 318 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 318 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 318 details
UrineDetected and Quantified0.0347 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0546 +/- 0.0420 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID318
FooDB IDFDB000604
KNApSAcK IDC00004635
Chemspider ID4444973
KEGG Compound IDC10084
BioCyc IDCPD-8004
BiGG IDNot Available
Wikipedia LinkIsorhamnetin
METLIN ID3445
PubChem Compound5281654
PDB IDNot Available
ChEBI ID6052
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000395
Good Scents IDrw1486311
References
Synthesis ReferenceHeap, 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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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. [PubMed:16097445 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  21. 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. [PubMed:15493462 ]
  22. 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. [PubMed:17368593 ]
  23. 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. [PubMed:17374653 ]
  24. 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. [PubMed:16963021 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Isorhamnetin → 6-{[3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Isorhamnetin → 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Isorhamnetin → 3,4,5-trihydroxy-6-[2-methoxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails