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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:42 UTC
Update Date2019-07-23 06:21:40 UTC
HMDB IDHMDB0036632
Secondary Accession Numbers
  • HMDB36632
Metabolite Identification
Common Name6-Hydroxyluteolin
Description6-Hydroxyluteolin is found in common thyme. 6-Hydroxyluteolin is isolated from Valerianella eriocarpa (Italian corn salad).
Structure
Data?1563862900
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
3',4',5,6,7-PentahydroxyflavoneChEBI
5,6,7,3',4'-PentahydroxyflavoneChEBI
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-oneHMDB
6-OH-LuteolinHMDB
Chemical FormulaC15H10O7
Average Molecular Weight302.2357
Monoisotopic Molecular Weight302.042652674
IUPAC Name2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one
Traditional Name6-hydroxyluteolin
CAS Registry Number18003-33-3
SMILES
OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H
InChI KeyVYAKIUWQLHRZGK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • 1,2-diphenol
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point284 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.36ALOGPS
logP2.1ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.8ChemAxon
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
Polarizability28.67 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, Positivesplash10-00di-0590000000-5c4ce3145edbe606eb36JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00kb-3601498000-0df82f4f2bd531b86b30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-fa0dde92bf21c90837d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0398000000-76f5cd48c1a3243242a6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi9-2950000000-3f3461a6eb81aaa54019JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-0a2c4e44ab43a09e3c24JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0269000000-35fe66a840935c38d5ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-5940000000-14e771feddad0eca4284JSpectraViewer | 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 ID278
FoodDB IDFDB015551
KNApSAcK IDC00003884
Chemspider ID4444961
KEGG Compound IDC10072
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281642
PDB IDNot Available
ChEBI ID2197
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 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
6-Hydroxyluteolin → 3,4,5-trihydroxy-6-[2-hydroxy-4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails
6-Hydroxyluteolin → 3,4,5-trihydroxy-6-[2-hydroxy-5-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails
6-Hydroxyluteolin → 6-{[2-(3,4-dihydroxyphenyl)-6,7-dihydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6-Hydroxyluteolin → 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6-Hydroxyluteolin → 6-{[2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-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
6-Hydroxyluteolin → [2-hydroxy-5-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl]oxidanesulfonic aciddetails