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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:38:18 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030667
Secondary Accession Numbers
  • HMDB30667
Metabolite Identification
Common NameChrysoeriol
DescriptionChrysoeriol, also known as 3'-O-methylluteolin, belongs to the class of organic compounds known as 3'-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods.
Structure
Data?1586983984
Synonyms
ValueSource
3'-MethoxyapigeninChEBI
3'-O-MethylluteolinChEBI
5,7,4'-Trihydroxy-3'-methoxyflavoneChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyroneChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
ChryseriolChEBI
Luteolin 3'-methyl etherChEBI
8-ChrysoeriolMeSH
ChrysoeriolChEBI
2-(5-Methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-oneHMDB
3'-Methoxy-4',5,7-trihydroxyflavoneHMDB
3'-O-MethyluteolinHMDB
4',5,7-Trihydroxy-3'-methoxy-flavoneHMDB
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
ScoparolHMDB
3’-Methoxy-4’,5,7-trihydroxyflavoneHMDB
3’-MethoxyapigeninHMDB
3’-O-MethylluteolinHMDB
5,7,4’-Trihydroxy-3’-methoxyflavoneHMDB
ChrysoriolHMDB
Luteolin 3’-methyl etherHMDB
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional Namechrysoeriol
CAS Registry Number491-71-4
SMILES
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3
InChI KeySCZVLDHREVKTSH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3'-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point330 - 331 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP3.07ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.58ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.38 m³·mol⁻¹ChemAxon
Polarizability29.74 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+171.00230932474
DeepCCS[M-H]-168.64430932474
DeepCCS[M-2H]-202.10430932474
DeepCCS[M+Na]+177.33130932474
AllCCS[M+H]+168.132859911
AllCCS[M+H-H2O]+164.432859911
AllCCS[M+NH4]+171.632859911
AllCCS[M+Na]+172.632859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-167.832859911
AllCCS[M+HCOO]-167.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChrysoeriolCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O14950.9Standard polar33892256
ChrysoeriolCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O13122.1Standard non polar33892256
ChrysoeriolCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O13261.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chrysoeriol,1TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3246.5Semi standard non polar33892256
Chrysoeriol,1TMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O3247.2Semi standard non polar33892256
Chrysoeriol,1TMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3302.7Semi standard non polar33892256
Chrysoeriol,2TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3113.5Semi standard non polar33892256
Chrysoeriol,2TMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3189.0Semi standard non polar33892256
Chrysoeriol,2TMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3233.8Semi standard non polar33892256
Chrysoeriol,3TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3138.0Semi standard non polar33892256
Chrysoeriol,1TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3510.6Semi standard non polar33892256
Chrysoeriol,1TBDMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O3508.3Semi standard non polar33892256
Chrysoeriol,1TBDMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3572.0Semi standard non polar33892256
Chrysoeriol,2TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3643.6Semi standard non polar33892256
Chrysoeriol,2TBDMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3728.0Semi standard non polar33892256
Chrysoeriol,2TBDMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3747.8Semi standard non polar33892256
Chrysoeriol,3TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3894.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoeriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zn9-0591000000-7220607989921b5eb2cf2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoeriol GC-MS (3 TMS) - 70eV, Positivesplash10-0ukc-2190860000-4372f124a3dd76bf7eee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoeriol 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 - Chrysoeriol ESI-TOF , Negative-QTOFsplash10-0udj-0159000000-3b5e183acbd84887fe162017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 20V, Negative-QTOFsplash10-0udj-0159000000-3b5e183acbd84887fe162017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 40V, Negative-QTOFsplash10-0a59-0190000000-e41a7a0b369e042fae342017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 50V, Negative-QTOFsplash10-057i-0590000000-9bcbe16e3cceb12dd4312017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 10V, Negative-QTOFsplash10-057i-0590000000-9bcbe16e3cceb12dd4312017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF , Negative-QTOFsplash10-0002-0091010000-c79a20e1046701a4b60a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 20V, Negative-QTOFsplash10-001j-0090000000-10b8cb8801e211ef50f32017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 40V, Negative-QTOFsplash10-0a59-0190000000-e41a7a0b369e042fae342017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 50V, Negative-QTOFsplash10-057i-0590000000-9bcbe16e3cceb12dd4312017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol ESI-TOF 10V, Negative-QTOFsplash10-0002-0091000000-bcccd2fe60d84477404f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol DI-ESI-qTof , Negative-QTOFsplash10-001i-0090000000-949568b80cb16a148dbc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0390000000-05ee89ba1f8ae9db73cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOFsplash10-0002-0090000000-1784fb1bc26ba2970df02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOFsplash10-001i-0090000000-8a5f685e7c770df2fae82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOFsplash10-0a59-0690000000-f42c517370ac99fa2b5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOFsplash10-001j-0090000000-10b8cb8801e211ef50f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOFsplash10-0a59-0190000000-e41a7a0b369e042fae342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOFsplash10-057i-0590000000-9bcbe16e3cceb12dd4312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-af2dad55a1de3a0bb83b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 10V, Positive-QTOFsplash10-0udi-0009000000-092a839c4ea4b680b7eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 20V, Positive-QTOFsplash10-0udi-0029000000-cbb434b2646e02f29d562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 40V, Positive-QTOFsplash10-0udi-2590000000-ff4ac1c0435d02e5a2a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 10V, Negative-QTOFsplash10-0002-0090000000-1080ec21704ad22b1e2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 20V, Negative-QTOFsplash10-0002-0090000000-7da56dabd16c2e5c217a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 40V, Negative-QTOFsplash10-0v0u-1390000000-a28554e987b0184da54f2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID282
FooDB IDFDB002579
KNApSAcK IDC00001029
Chemspider ID4444263
KEGG Compound IDC04293
BioCyc ID574-TRIHYDROXY-3-METHOXYFLAVONE
BiGG IDNot Available
Wikipedia LinkChrysoeriol
METLIN IDNot Available
PubChem Compound5280666
PDB IDNot Available
ChEBI ID16514
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cha BY, Shi WL, Yonezawa T, Teruya T, Nagai K, Woo JT: An inhibitory effect of chrysoeriol on platelet-derived growth factor (PDGF)-induced proliferation and PDGF receptor signaling in human aortic smooth muscle cells. J Pharmacol Sci. 2009 May;110(1):105-10. Epub 2009 May 8. [PubMed:19423953 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .