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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:08 UTC
Update Date2019-07-23 06:07:20 UTC
HMDB IDHMDB0030802
Secondary Accession Numbers
  • HMDB30802
Metabolite Identification
Common NamePatuletin
DescriptionPatuletin is found in german camomile. Patuletin is a pigment from flowers of French marigold Tagetes patul
Structure
Data?1563862040
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyroneChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-oneChEBI
3',4',5,7-Tetrahydroxy-6-methoxyflavonolChEBI
3,5,7,3',4'-Pentahydroxy-6-methoxyflavoneChEBI
6-MethoxyquercetinChEBI
6-O-MethylquercetagetinChEBI
Quercetagetin 6-methyl etherChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC16H12O8
Average Molecular Weight332.2617
Monoisotopic Molecular Weight332.05321736
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-chromen-4-one
Traditional Namepatuletin
CAS Registry Number519-96-0
SMILES
COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3
InChI KeyJMIFIYIEXODVTO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonols. These 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
  • 6-methoxyflavonoid-skeleton
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Catechol
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point262 - 264 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP1.82ALOGPS
logP2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.95ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.33 m³·mol⁻¹ChemAxon
Polarizability31.49 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0529000000-80eb16e79922e773ce42JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-0024029000-5b6566c1e3d3b3e22ad5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-0433b24ac8fa3594d2efJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0109000000-8ce46b5c40f4ed741ffdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-4921000000-98be6ac7065ad4f7fb0cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0109000000-0074b1f85f21aec6fa6fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0139000000-11cfd247fb3babf52f64JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-6941000000-01e1b2cba8f4e48697a6JSpectraViewer | MoNA
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 IDNot Available
Phenol Explorer Compound ID353
FoodDB IDFDB002744
KNApSAcK IDC00004680
Chemspider ID4444997
KEGG Compound IDC10118
BioCyc IDCPD-14907
BiGG IDNot Available
Wikipedia LinkPatuletin
METLIN IDNot Available
PubChem Compound5281678
PDB IDNot Available
ChEBI ID75164
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Patuletin → Spinacetindetails
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
Patuletin → 6-{[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-6-methoxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Patuletin → 6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Patuletin → 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Patuletin → 3,4,5-trihydroxy-6-[2-hydroxy-4-(3,5,7-trihydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails
Patuletin → 3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-6-methoxy-4-oxo-4H-chromen-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
Patuletin → [2-hydroxy-5-(3,5,7-trihydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)phenyl]oxidanesulfonic aciddetails