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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:59 UTC
Update Date2020-02-26 21:44:09 UTC
HMDB IDHMDB0029676
Secondary Accession Numbers
  • HMDB29676
Metabolite Identification
Common NameDiosmetin
DescriptionDiosmetin, also known as 4'-methylluteolin or vitamin p, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, diosmetin is considered to be a flavonoid lipid molecule. Diosmetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Diosmetin has been detected, but not quantified in, several different foods, such as common sages, lemons, dills, lemon verbena, and sweet marjorams. This could make diosmetin a potential biomarker for the consumption of these foods. Diosmetin is an O-methylated flavone and the aglycone part of the flavonoid glycosides diosmin that occurs naturally in citrus fruits .
Structure
Data?1582753449
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxyflavoneChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyroneChEBI
Luteolin 4'-methyl etherChEBI
SalinigricoflavonolChEBI
4'-MethylluteolinHMDB
5,7,3'-Trihydroxy-4'-methoxyflavoneHMDB
Vitamin pHMDB
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Traditional Namediosmetin
CAS Registry Number520-34-3
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
InChI KeyMBNGWHIJMBWFHU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 3'-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

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.10Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP3.06ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
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
Polarizability29.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available164.785http://allccs.zhulab.cn/database/detail?ID=AllCCS00001489

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Diosmetin,1TMS,#13261.9888https://arxiv.org/abs/1905.12712
Diosmetin,1TMS,#23333.535https://arxiv.org/abs/1905.12712
Diosmetin,1TMS,#33283.8052https://arxiv.org/abs/1905.12712
Diosmetin,2TMS,#13140.94https://arxiv.org/abs/1905.12712
Diosmetin,2TMS,#23212.0322https://arxiv.org/abs/1905.12712
Diosmetin,2TMS,#33269.2917https://arxiv.org/abs/1905.12712
Diosmetin,3TMS,#13153.801https://arxiv.org/abs/1905.12712
Diosmetin,1TBDMS,#13518.4963https://arxiv.org/abs/1905.12712
Diosmetin,1TBDMS,#23599.3652https://arxiv.org/abs/1905.12712
Diosmetin,1TBDMS,#33556.6985https://arxiv.org/abs/1905.12712
Diosmetin,2TBDMS,#13656.4888https://arxiv.org/abs/1905.12712
Diosmetin,2TBDMS,#23744.4485https://arxiv.org/abs/1905.12712
Diosmetin,2TBDMS,#33767.6238https://arxiv.org/abs/1905.12712
Diosmetin,3TBDMS,#13897.9268https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kh9-0492000000-c9cb489c6e399645f54f2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ukc-2190860000-1029bf37ad921c9a81e82017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014u-0000700009-50048523dd30a3c691262017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014u-0000700009-50048523dd30a3c691262017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0190000000-77edda567cd76512c52d2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-675379707ad9e98244a92017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0091000000-188fb9f96e76251ce5392017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0190000000-77edda567cd76512c52d2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-001i-0090000000-ae5188debe4910fab9c62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-6e1198f4157cda4df0ac2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-b23157e3c53d703e88d12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-675379707ad9e98244a92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0190000000-77edda567cd76512c52d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0094000000-0b3f48256d5c0ee7fb1b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-000i-0092000000-0448ee3b6390176e376a2020-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 21V, positivesplash10-000i-0090000000-8bb45858bd3dc65a5c072020-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-a4a0986393c64d566f912015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-9488c8767caac5f6b9b52015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-2590000000-e4455d0da36912d7b96a2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-91f51b4b036d4731f3052015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-b6f4a2a03e7355f95b1c2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-0390000000-e296a45296f81b0f14542015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-4cf9dd217b03f450a62e2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0039000000-21f9279ab01ca5ee3dd42021-09-07View 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 IDDB11259
Phenol Explorer Compound ID241
FooDB IDFDB000861
KNApSAcK IDC00001036
Chemspider ID4444931
KEGG Compound IDC10038
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiosmetin
METLIN IDNot Available
PubChem Compound5281612
PDB IDNot Available
ChEBI ID4630
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.. .

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
Diosmetin → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
Diosmetin → Diosmetin 7-O-beta-D-glucuronopyranosidedetails
Diosmetin → 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenoxy]-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
Diosmetin → [5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]oxidanesulfonic aciddetails