Showing Compound Card for Isorhamnetin (CDB004938)

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Record Information
Version1.0
Created at2020-04-17 18:52:30 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB004938
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsorhamnetin
DescriptionIsorhamnetin, also known as 3-methylquercetin, 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. Thus, isorhamnetin is considered to be a flavonoid lipid molecule. A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. Isorhamnetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isorhamnetin exists in all eukaryotes, ranging from yeast to humans. Isorhamnetin is a bitter tasting compound. Outside of the human body, Isorhamnetin is found, on average, in the highest concentration within a few different foods, such as parsley, green bell peppers, and dills and in a lower concentration in romaine lettuces, chinese cabbages, and pears. Isorhamnetin has also been detected, but not quantified in, several different foods, such as lemons, agars, chickpea, apples, and cucurbita. This could make isorhamnetin a potential biomarker for the consumption of these foods. Isorhamnetin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight316.26
Monoisotopic Molecular Weight316.0583
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point311 - 314 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsorhamnetin, non-derivatized, GC-MS Spectrumsplash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
GC-MSIsorhamnetin, non-derivatized, GC-MS Spectrumsplash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
Predicted GC-MSIsorhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0591000000-2e1f6e28bf0d47d5e240Spectrum
Predicted GC-MSIsorhamnetin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001u-0041090000-7e13d91dc4b2bd93fc17Spectrum
Predicted GC-MSIsorhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0394000000-f903b8df9b79e6a94f442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0956000000-6286c6784746c9eba0e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0219000000-c620190cc3878a4242f92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-1941000000-10313269e61a0584f37f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0109000000-082620470bd7fd8a68972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0491000000-da6ec11ed89cc64a79722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-141b68c1e564685b35ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-8fa57905e16cdfcc4e9e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0493000000-2b88769e97319b5f076c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0udi-1940000000-51e0d426523f81faa98b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0gb9-0009000000-caca1c7784ed9828dfb42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-0233e63233dadf52ffc52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0zfr-0952000000-13e1d438b3f800cfc18a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0209000000-89d7fc697d82018c12282021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-0209000000-405d086d8e4de2b975b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-1910000000-170b80b866f2075e44e92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0029000000-a9da21c499e339f09ac62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0493000000-14bbb49d59d91543a76e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-3458ddb4f7ba64eb81c82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-bb7cbcffdd9f296b6b9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0079000000-c73663231834b1b1b79a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-3790000000-3b8ca78684ffcba51bf12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-57dd2505d869c8f411dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0169000000-38b50b4081dff638023b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frb-3890000000-3525a3f4676b6a964b712016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00174 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00103 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.000392 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.000745 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.000576 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00117 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0002655
DrugBank IDNot Available
Phenol Explorer Compound ID318
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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