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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:46:49 UTC
Update Date2021-10-13 06:57:41 UTC
HMDB IDHMDB0036619
Secondary Accession Numbers
  • HMDB36619
Metabolite Identification
Common Name5,7-Dihydroxyflavone
Description5,7-Dihydroxyflavone 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. 5,7-Dihydroxyflavone is a bitter tasting compound. 5,7-Dihydroxyflavone has been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), sour cherries (Prunus cerasus), sweet oranges (Citrus sinensis), and wild carrots (Daucus carota). This could make 5,7-dihydroxyflavone a potential biomarker for the consumption of these foods. 5,7-Dihydroxyflavone 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 5,7-Dihydroxyflavone.
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-DihydroxyflavoneChEBI
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ciHMDB
ChrysinHMDB
Chrysinic acidHMDB
Ois 3HMDB
ChrysineMeSH
5,7-Dihydroxy-flavoneMeSH
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

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point285.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point491.91 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility84 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.520The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available151.684http://allccs.zhulab.cn/database/detail?ID=AllCCS00001433
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP10(3.44) g/LALOGPS
logP10(3.01) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7-DihydroxyflavoneOC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C13917.0Standard polar33892256
5,7-DihydroxyflavoneOC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C12657.4Standard non polar33892256
5,7-DihydroxyflavoneOC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C12707.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxyflavone,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C12786.9Semi standard non polar33892256
5,7-Dihydroxyflavone,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=CC=C1)O22736.5Semi standard non polar33892256
5,7-Dihydroxyflavone,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C12803.8Semi standard non polar33892256
5,7-Dihydroxyflavone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C13046.4Semi standard non polar33892256
5,7-Dihydroxyflavone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=CC=C1)O23002.3Semi standard non polar33892256
5,7-Dihydroxyflavone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C13261.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (2 TMS)splash10-001i-2839000000-d0964f24f611d1c14e952014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (Non-derivatized)splash10-001i-2839000000-d0964f24f611d1c14e952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7-Dihydroxyflavone GC-EI-TOF (Non-derivatized)splash10-001i-0619000000-53f48b2cf9bad74e8f652017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0690000000-b07283fbd904f2901dd62017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-4439000000-26a54787c8758b70201f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF , Negative-QTOFsplash10-0002-0020900000-2dbcc5b06309066d63b52017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 26V, Negative-QTOFsplash10-0udi-0290000000-bdd70471bc805c9009b22017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 40V, Negative-QTOFsplash10-0fr6-0900000000-eee4ea35750adc10ef1b2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF , Negative-QTOFsplash10-0udi-0090000000-2f6b543a5679e285552a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 26V, Negative-QTOFsplash10-0udi-0290000000-bdd70471bc805c9009b22017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 40V, Negative-QTOFsplash10-0fr6-0900000000-eee4ea35750adc10ef1b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone DI-ESI-qTof , Negative-QTOFsplash10-0udi-0490000000-554518d0a352f29f80932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone DI-ESI-qTof , Positive-QTOFsplash10-0zfr-0950000000-51b2794dec3e6f6eea6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-9cc0f49937b1a8fa0b342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-66cd77f4bd910deb01032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0290000000-10a8a1236031b97efe7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0fr6-0920000000-19bbcaf4a2423b2cb49d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-014m-0900000000-200355de722ac7f96ef72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-ac2af4316665e2509d892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0190000000-8f5ac4706417c39a2d622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOFsplash10-0gbc-0900000000-d619653decf40895a5112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOFsplash10-0a4i-0390000000-eb3159b6ffe6b7c816b22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOFsplash10-006t-3930000000-3775c8b9ef4bbb0cb3522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOFsplash10-0udi-0090000000-c8b5dd372a2667398b012017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 10V, Positive-QTOFsplash10-0a4i-0090000000-c8a1f1ae722a2b79308a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 20V, Positive-QTOFsplash10-0a4i-0090000000-191437b0a57325aec07a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 40V, Positive-QTOFsplash10-0udr-4950000000-f1f4abaafec11c5008902015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 10V, Negative-QTOFsplash10-0udi-0090000000-4c48fd26f99d65b20cd92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 20V, Negative-QTOFsplash10-0udi-0090000000-acfd169c302ecc539f582015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 40V, Negative-QTOFsplash10-0udi-1940000000-98ef8f11854760675c832015-04-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1229801
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