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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:32 UTC
Update Date2020-02-26 21:44:02 UTC
HMDB IDHMDB0029620
Secondary Accession Numbers
  • HMDB29620
Metabolite Identification
Common NameTricetin
DescriptionTricetin belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, tricetin is considered to be a flavonoid. Tricetin is a bitter tasting compound. Tricetin has been detected, but not quantified in, several different foods, such as ginkgo nuts (Ginkgo biloba), green tea, pulses, red tea, and black tea. This could make tricetin a potential biomarker for the consumption of these foods. Tricetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Tricetin.
Structure
Data?1582753442
Synonyms
ValueSource
3',4',5,5',7-PentahydroxyflavoneChEBI
5,7,3',4',5'-PentahydroxyflavoneChEBI
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-oneMeSH
5,7,3,4,5-PentahydroxyflavoneHMDB
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
MYFHMDB
Chemical FormulaC15H10O7
Average Molecular Weight302.2357
Monoisotopic Molecular Weight302.042652674
IUPAC Name5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Nametricetin
CAS Registry Number520-31-0
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H10O7/c16-7-3-8(17)14-9(18)5-12(22-13(14)4-7)6-1-10(19)15(21)11(20)2-6/h1-5,16-17,19-21H
InChI KeyARSRJFRKVXALTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point330 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.29ALOGPS
logP2.1ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.57ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.88 m³·mol⁻¹ChemAxon
Polarizability28.66 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Tricetin,1TMS,#13469.8586https://arxiv.org/abs/1905.12712
Tricetin,1TMS,#23405.4324https://arxiv.org/abs/1905.12712
Tricetin,1TMS,#33441.8367https://arxiv.org/abs/1905.12712
Tricetin,1TMS,#43424.5508https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#13389.0486https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#23396.912https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#33412.0464https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#43309.8716https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#53339.3794https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#63349.0557https://arxiv.org/abs/1905.12712
Tricetin,2TMS,#73298.191https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#13209.216https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#23347.802https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#33245.763https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#43207.5483https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#53186.4954https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#63152.0935https://arxiv.org/abs/1905.12712
Tricetin,3TMS,#73192.0232https://arxiv.org/abs/1905.12712
Tricetin,4TMS,#13281.4944https://arxiv.org/abs/1905.12712
Tricetin,4TMS,#23245.2903https://arxiv.org/abs/1905.12712
Tricetin,4TMS,#33174.7554https://arxiv.org/abs/1905.12712
Tricetin,4TMS,#43129.4534https://arxiv.org/abs/1905.12712
Tricetin,5TMS,#13272.1443https://arxiv.org/abs/1905.12712
Tricetin,1TBDMS,#13752.6172https://arxiv.org/abs/1905.12712
Tricetin,1TBDMS,#23694.7905https://arxiv.org/abs/1905.12712
Tricetin,1TBDMS,#33738.0222https://arxiv.org/abs/1905.12712
Tricetin,1TBDMS,#43706.9675https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#13982.804https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#24002.4033https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#33962.3174https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#43945.7173https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#53916.7222https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#63974.4292https://arxiv.org/abs/1905.12712
Tricetin,2TBDMS,#73898.8303https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#14054.4111https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#24124.759https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#34110.715https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#44059.366https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#54028.0894https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#63984.526https://arxiv.org/abs/1905.12712
Tricetin,3TBDMS,#74013.3918https://arxiv.org/abs/1905.12712
Tricetin,4TBDMS,#14229.064https://arxiv.org/abs/1905.12712
Tricetin,4TBDMS,#24184.7905https://arxiv.org/abs/1905.12712
Tricetin,4TBDMS,#34171.3022https://arxiv.org/abs/1905.12712
Tricetin,4TBDMS,#44104.8467https://arxiv.org/abs/1905.12712
Tricetin,5TBDMS,#14329.9937https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uki-0691000000-88f18a856d20d64a9d7d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0002-1013059000-95ee4443442210260b102017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0901000000-f56262960dba956afd502017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0006-0901000000-f56262960dba956afd502017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b922017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-3dcc5d7fef903a3c09f52017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0002-0901000000-adca52e8c5d4d614e5902017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b922017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0198000000-cba95552c614a2f9b7e72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0059000000-b7e0731c9dbeb70ddeb12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0fb9-0922000000-9e56c907be227f02313b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0fb9-0922000000-44709dc0d0320556b03f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-3dcc5d7fef903a3c09f52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0002-0901000000-adca52e8c5d4d614e5902017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0290000000-0f57575f574a95305eb82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0290000000-8d5cb27fdf5674bad3d32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0290000000-2d8433bfc6706f733d6c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0290000000-34ded98bef3c50e30b292017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-2fc4f29a425d7615cf062021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-8e740cef01c2d073c39d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-55f2245ee61168ca65122021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-2639c7ffa8fd21499e872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159000000-5bcb1791e18c9991237c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-4690000000-f0fd1c4e0a31338873c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-7f4283df70683b988cfd2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-702e4fc650b6dfb6c68d2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0540-5970000000-cbadd30d87aae8c98ab92016-08-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08230
Phenol Explorer Compound IDNot Available
FooDB IDFDB000790
KNApSAcK IDC00013328
Chemspider ID4445018
KEGG Compound IDC10192
BioCyc IDCPD-12570
BiGG IDNot Available
Wikipedia LinkTricetin
METLIN IDNot Available
PubChem Compound5281701
PDB IDMYF
ChEBI ID507499
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pistelli L, Bertoli A, Noccioli C, Mendez J, Musmanno RA, Di Maggio T, Coratza G: Antimicrobial activity of Inga fendleriana extracts and isolated flavonoids. Nat Prod Commun. 2009 Dec;4(12):1679-83. [PubMed:20120106 ]
  2. Geraets L, Haegens A, Brauers K, Haydock JA, Vernooy JH, Wouters EF, Bast A, Hageman GJ: Inhibition of LPS-induced pulmonary inflammation by specific flavonoids. Biochem Biophys Res Commun. 2009 May 8;382(3):598-603. doi: 10.1016/j.bbrc.2009.03.071. Epub 2009 Mar 16. [PubMed:19292976 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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
Tricetin → 3,4,5-trihydroxy-6-{[5-hydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails
Tricetin → 3,4,5-trihydroxy-6-{[7-hydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
Tricetin → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2,6-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Tricetin → 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails