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Showing metabocard for Tamarixetin (HMDB0002937)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2019-01-11 19:17:18 UTC
HMDB IDHMDB0002937
Secondary Accession Numbers
  • HMDB02937
Metabolite Identification
Common NameTamarixetin
DescriptionTamarixetin is a flavanoid component of the Ginko Biloba extract. Exhibits antioxidant properties.
Structure
Data?1547234238
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
DihydrotamarixetinChEMBL
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0942000000-243d67f1bef64e8ec397View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002f-2430090000-e78153eb3884bd8edb1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0109000000-214294e6786df702f543View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0925000000-96df061b2c051eba81fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-3900000000-986176e74a8e3aed42ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0309000000-2c0940e32c2ac06d9454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0925000000-80ccd9f800335c4efcf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbl-3910000000-95fddf0306ab882ab5a7View in MoNA
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
FoodDB IDFDB016383
KNApSAcK IDC00004636
Chemspider ID423348
KEGG Compound IDC10188
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTamarixetin
METLIN ID3446
PubChem Compound482576
PDB IDNot Available
ChEBI ID542812
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

Enzyme Details
1. Sulfotransferase family cytosolic 2B member 1
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
Enzyme Details
2. 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
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
Enzyme Details
3. Sulfotransferase 1A3
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