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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:46:49 UTC
Update Date2019-07-23 06:21:38 UTC
HMDB IDHMDB0036619
Secondary Accession Numbers
  • HMDB36619
Metabolite Identification
Common Name5,7-Dihydroxyflavone
Description5,7-Dihydroxyflavone, also known as chrysin or ois 3, 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, 5,7-dihydroxyflavone is considered to be a flavonoid lipid molecule. 5,7-Dihydroxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5,7-Dihydroxyflavone is a bitter tasting compound. Outside of the human body, 5,7-dihydroxyflavone has been detected, but not quantified in, several different foods, such as carrots, sour cherries, sweet oranges, and wild carrots. This could make 5,7-dihydroxyflavone a potential biomarker for the consumption of these foods. 5,7-Dihydroxyflavone is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC).
Structure
Data?1563862898
Synonyms
ValueSource
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-2-phenyl-4H-benzo(b)pyran-4-oneChEBI
5,7-Dihydroxy-2-phenylchromen-4-oneChEBI
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ciHMDB
ChrysinHMDB
Chrysinic acidHMDB
Ois 3HMDB
ChrysineMeSH
5,7-Dihydroxy-flavoneMeSH
5,7-DihydroxyflavoneChEBI
Chemical FormulaC15H10O4
Average Molecular Weight254.2375
Monoisotopic Molecular Weight254.057908808
IUPAC Name5,7-dihydroxy-2-phenyl-4H-chromen-4-one
Traditional Namechrysin
CAS Registry Number480-40-0
SMILES
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
InChI KeyRTIXKCRFFJGDFG-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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP3.44ALOGPS
logP3.01ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.93 m³·mol⁻¹ChemAxon
Polarizability25.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2839000000-d0964f24f611d1c14e95Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2839000000-d0964f24f611d1c14e95Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0619000000-53f48b2cf9bad74e8f65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0690000000-b07283fbd904f2901dd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-4439000000-26a54787c8758b70201fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0020900000-2dbcc5b06309066d63b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-0udi-0290000000-bdd70471bc805c9009b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fr6-0900000000-eee4ea35750adc10ef1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0090000000-2f6b543a5679e285552aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-0udi-0290000000-bdd70471bc805c9009b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fr6-0900000000-eee4ea35750adc10ef1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0490000000-554518d0a352f29f8093Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0zfr-0950000000-51b2794dec3e6f6eea6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-9cc0f49937b1a8fa0b34Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-66cd77f4bd910deb0103Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0290000000-10a8a1236031b97efe7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fr6-0920000000-19bbcaf4a2423b2cb49dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014m-0900000000-200355de722ac7f96ef7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-ac2af4316665e2509d89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190000000-8f5ac4706417c39a2d62Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gbc-0900000000-d619653decf40895a511Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0390000000-eb3159b6ffe6b7c816b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-006t-3930000000-3775c8b9ef4bbb0cb352Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-c8b5dd372a2667398b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c8a1f1ae722a2b79308aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-191437b0a57325aec07aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-4950000000-f1f4abaafec11c500890Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-4c48fd26f99d65b20cd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-acfd169c302ecc539f58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1940000000-98ef8f11854760675c83Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 ID240
FooDB IDFDB015535
KNApSAcK IDC00003794
Chemspider ID4444926
KEGG Compound IDC10028
BioCyc IDCPD-8184
BiGG IDNot Available
Wikipedia LinkChrysin
METLIN IDNot Available
PubChem Compound5281607
PDB IDNot Available
ChEBI ID75095
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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
5,7-Dihydroxyflavone → 3,4,5-trihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails
5,7-Dihydroxyflavone → 3,4,5-trihydroxy-6-[(7-hydroxy-4-oxo-2-phenyl-4H-chromen-5-yl)oxy]oxane-2-carboxylic aciddetails