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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002937
Secondary Accession Numbers
  • HMDB02937
Metabolite Identification
Common NameTamarixetin
DescriptionTamarixetin belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Tamarixetin is an extremely weak basic (essentially neutral) compound (based on its pKa). Tamarixetin is an O-methylated flav-on-ol, a naturally occurring flavonoid. Outside of the human body, Tamarixetin has been detected, but not quantified in, tea. This could make tamarixetin a potential biomarker for the consumption of these foods.
Structure
Data?1582752259
Synonyms
ValueSource
DihydrotamarixetinHMDB
3,3',5,7-Tetrahydroxy-4'-methoxyflavoneHMDB
Chemical FormulaC16H14O7
Average Molecular Weight318.2782
Monoisotopic Molecular Weight318.073952802
IUPAC Name3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namequercetin 4'-methyl ether
CAS Registry Number603-61-2
SMILES
COC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O
InChI Identifier
InChI=1S/C16H14O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,15-19,21H,1H3
InChI KeyKQNGHARGJDXHKF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Flavanonol
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP1.32ALOGPS
logP1.96ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.09 m³·mol⁻¹ChemAxon
Polarizability31.06 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
DarkChem[M+H]+174.91631661259
DarkChem[M-H]-176.47731661259
DeepCCS[M+H]+171.55530932474
DeepCCS[M-H]-169.16730932474
DeepCCS[M-2H]-203.48930932474
DeepCCS[M+Na]+179.14130932474
AllCCS[M+H]+174.432859911
AllCCS[M+H-H2O]+170.932859911
AllCCS[M+NH4]+177.632859911
AllCCS[M+Na]+178.632859911
AllCCS[M-H]-173.332859911
AllCCS[M+Na-2H]-172.932859911
AllCCS[M+HCOO]-172.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TamarixetinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O4462.3Standard polar33892256
TamarixetinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O3031.0Standard non polar33892256
TamarixetinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O3041.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tamarixetin,1TMS,isomer #1COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O)C=C1O[Si](C)(C)C3124.5Semi standard non polar33892256
Tamarixetin,1TMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)C2O)C=C1O3150.1Semi standard non polar33892256
Tamarixetin,1TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2O)C=C1O3150.5Semi standard non polar33892256
Tamarixetin,1TMS,isomer #4COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O[Si](C)(C)C)C=C1O3050.2Semi standard non polar33892256
Tamarixetin,2TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)C2O)C=C1O[Si](C)(C)C3026.0Semi standard non polar33892256
Tamarixetin,2TMS,isomer #2COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2O)C=C1O[Si](C)(C)C3027.0Semi standard non polar33892256
Tamarixetin,2TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C2953.1Semi standard non polar33892256
Tamarixetin,2TMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)C2O)C=C1O3057.4Semi standard non polar33892256
Tamarixetin,2TMS,isomer #5COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)C2O[Si](C)(C)C)C=C1O2930.9Semi standard non polar33892256
Tamarixetin,2TMS,isomer #6COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2O[Si](C)(C)C)C=C1O2977.8Semi standard non polar33892256
Tamarixetin,3TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)C2O)C=C1O[Si](C)(C)C2997.0Semi standard non polar33892256
Tamarixetin,3TMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C2865.1Semi standard non polar33892256
Tamarixetin,3TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C2908.1Semi standard non polar33892256
Tamarixetin,3TMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)C2O[Si](C)(C)C)C=C1O2916.9Semi standard non polar33892256
Tamarixetin,4TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C2916.8Semi standard non polar33892256
Tamarixetin,1TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O)C=C1O[Si](C)(C)C(C)(C)C3379.6Semi standard non polar33892256
Tamarixetin,1TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)C2O)C=C1O3406.3Semi standard non polar33892256
Tamarixetin,1TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O)C=C1O3410.5Semi standard non polar33892256
Tamarixetin,1TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O3352.4Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)C2O)C=C1O[Si](C)(C)C(C)(C)C3544.1Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O)C=C1O[Si](C)(C)C(C)(C)C3545.3Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3485.9Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O)C=C1O3564.9Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #5COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O3457.0Semi standard non polar33892256
Tamarixetin,2TBDMS,isomer #6COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O3503.7Semi standard non polar33892256
Tamarixetin,3TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O)C=C1O[Si](C)(C)C(C)(C)C3694.7Semi standard non polar33892256
Tamarixetin,3TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3601.6Semi standard non polar33892256
Tamarixetin,3TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3620.3Semi standard non polar33892256
Tamarixetin,3TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O3644.1Semi standard non polar33892256
Tamarixetin,4TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3785.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tamarixetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0942000000-243d67f1bef64e8ec3972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tamarixetin GC-MS (4 TMS) - 70eV, Positivesplash10-002f-2430090000-e78153eb3884bd8edb1a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tamarixetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tamarixetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 10V, Positive-QTOFsplash10-014i-0109000000-214294e6786df702f5432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 20V, Positive-QTOFsplash10-0uxr-0925000000-96df061b2c051eba81fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 40V, Positive-QTOFsplash10-0uki-3900000000-986176e74a8e3aed42ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 10V, Negative-QTOFsplash10-014i-0309000000-2c0940e32c2ac06d94542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 20V, Negative-QTOFsplash10-0gb9-0925000000-80ccd9f800335c4efcf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 40V, Negative-QTOFsplash10-0pbl-3910000000-95fddf0306ab882ab5a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 10V, Negative-QTOFsplash10-014i-0009000000-bf47ad651d2af1b091442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 20V, Negative-QTOFsplash10-014i-0309000000-4f56e4ee0972dae05af22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 40V, Negative-QTOFsplash10-0a59-2900000000-262acfca5032dda41efe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 10V, Positive-QTOFsplash10-014i-0509000000-07dd9e06c9a656c5cb4b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 20V, Positive-QTOFsplash10-0gdi-0906000000-1601e6e6e99b2c1666eb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamarixetin 40V, Positive-QTOFsplash10-0udi-0900000000-97b177f72d54ce0fe5192021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00429 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016577
KNApSAcK IDC00004636
Chemspider ID423348
KEGG Compound IDC10188
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTamarixetin
METLIN ID3446
PubChem Compound482576
PDB IDNot Available
ChEBI ID542812
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRao, Koppaka V.; Owoyale, Jacob A. Partial methylation of quercetin: direct synthesis of tamarixetin, ombuin and ayanin. Journal of Heterocyclic Chemistry (1976), 13(6), 1293-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nielsen SE, Freese R, Kleemola P, Mutanen M: Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2002 May;11(5):459-66. [PubMed:12010860 ]
  2. Brevik A, Rasmussen SE, Drevon CA, Andersen LF: Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2004 May;13(5):843-9. [PubMed:15159318 ]
  3. (). Wu, Z., Smith, J. V., Paramasivam, V., Butko, P., Khan, I., Cypser, J. R., and Luo, Y. (2002). Ginkgo biloba extract EGb 761 increases stress resistance and extends life span of caenoraibditis elegans. Cell Mol Biol (Noisy-le-grand) 48, 725-31.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Tamarixetin → [5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxidanesulfonic aciddetails
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
Tamarixetin → 6-{[3,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Tamarixetin → 6-{[3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Tamarixetin → 3,4,5-trihydroxy-6-[2-methoxy-5-(3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Tamarixetin → [2-methoxy-5-(3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails