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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:39:25 UTC
Update Date2019-07-23 06:26:23 UTC
HMDB IDHMDB0038356
Secondary Accession Numbers
  • HMDB38356
Metabolite Identification
Common NameSideritiflavone
DescriptionSideritiflavone belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, sideritiflavone is considered to be a flavonoid. Sideritiflavone has been detected, but not quantified in, a few different foods, such as herbs and spices, peppermints (Mentha X piperita), and spearmints (Mentha spicata). This could make sideritiflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sideritiflavone.
Structure
Data?1563863183
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-oneHMDB
3',4',5-Trihydroxy-6,7,8-trimethoxyflavoneHMDB
5,3',4'-Trihydroxy-6,7,8-trimethoxyflavoneHMDB
SideritoflavoneHMDB
Chemical FormulaC18H16O8
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
Traditional Namesideritiflavone
CAS Registry Number70360-12-2
SMILES
COC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C18H16O8/c1-23-16-14(22)13-11(21)7-12(8-4-5-9(19)10(20)6-8)26-15(13)17(24-2)18(16)25-3/h4-7,19-20,22H,1-3H3
InChI KeyUWNUJPINKMRKKR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 - 198 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP2.65ALOGPS
logP2.23ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.66ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.3 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available184.89731661259
DarkChem[M-H]-PredictedNot Available186.23731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Sideritiflavone,1TMS,#13297.5117https://arxiv.org/abs/1905.12712
Sideritiflavone,1TMS,#23374.0251https://arxiv.org/abs/1905.12712
Sideritiflavone,1TMS,#33380.022https://arxiv.org/abs/1905.12712
Sideritiflavone,2TMS,#13322.734https://arxiv.org/abs/1905.12712
Sideritiflavone,2TMS,#23301.1624https://arxiv.org/abs/1905.12712
Sideritiflavone,2TMS,#33293.771https://arxiv.org/abs/1905.12712
Sideritiflavone,3TMS,#13217.5444https://arxiv.org/abs/1905.12712
Sideritiflavone,1TBDMS,#13561.6914https://arxiv.org/abs/1905.12712
Sideritiflavone,1TBDMS,#23587.5945https://arxiv.org/abs/1905.12712
Sideritiflavone,1TBDMS,#33601.5034https://arxiv.org/abs/1905.12712
Sideritiflavone,2TBDMS,#13784.1567https://arxiv.org/abs/1905.12712
Sideritiflavone,2TBDMS,#23743.4092https://arxiv.org/abs/1905.12712
Sideritiflavone,2TBDMS,#33743.7485https://arxiv.org/abs/1905.12712
Sideritiflavone,3TBDMS,#13886.7683https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0119000000-d661f929d6e7c6e1e2a62017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-1030190000-da25a150ef664eff6f062017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-341009b391d78207b8af2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-0f73369acc39d5f937642016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cfr-2977000000-3274aff2824af897c04a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-9bdb314df607331460dc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0019000000-4a242a4a1e57df1b55522016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9271000000-f83431b833cacf2df46e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-1b2458f70b43c2827ff82021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aou-0009000000-3415977c64a46461f5ee2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-ef0e36da9abfe27aa0762021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-c383b2e8879413a775be2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-0249000000-439492fde1587ad3646e2021-09-23View 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 IDNot Available
FooDB IDFDB017693
KNApSAcK IDC00003927
Chemspider ID136978
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155493
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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.. .