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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:59 UTC
Update Date2022-03-07 02:52:15 UTC
HMDB IDHMDB0029676
Secondary Accession Numbers
  • HMDB29676
Metabolite Identification
Common NameDiosmetin
DescriptionDiosmetin 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. Diosmetin has been detected, but not quantified in, several different foods, such as sweet marjorams (Origanum majorana), rosemaries (Rosmarinus officinalis), common thymes (Thymus vulgaris), lemons (Citrus limon), and common oreganos (Origanum vulgare). This could make diosmetin a potential biomarker for the consumption of these foods. Diosmetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Diosmetin.
Structure
Data?1582753449
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxyflavoneChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyroneChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
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

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 230 °CNot Available
Boiling Point576.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility104.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.10Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available164.785http://allccs.zhulab.cn/database/detail?ID=AllCCS00001489
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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+172.34830932474
DeepCCS[M-H]-169.9930932474
DeepCCS[M-2H]-203.63230932474
DeepCCS[M+Na]+178.85930932474
AllCCS[M+H]+168.532859911
AllCCS[M+H-H2O]+164.832859911
AllCCS[M+NH4]+172.032859911
AllCCS[M+Na]+172.932859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-167.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiosmetinCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O4937.0Standard polar33892256
DiosmetinCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O3146.9Standard non polar33892256
DiosmetinCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O3283.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diosmetin,1TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C3262.0Semi standard non polar33892256
Diosmetin,1TMS,isomer #2COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O3333.5Semi standard non polar33892256
Diosmetin,1TMS,isomer #3COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O3283.8Semi standard non polar33892256
Diosmetin,2TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C3140.9Semi standard non polar33892256
Diosmetin,2TMS,isomer #2COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C3212.0Semi standard non polar33892256
Diosmetin,2TMS,isomer #3COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1O3269.3Semi standard non polar33892256
Diosmetin,3TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C3153.8Semi standard non polar33892256
Diosmetin,1TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3518.5Semi standard non polar33892256
Diosmetin,1TBDMS,isomer #2COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O3599.4Semi standard non polar33892256
Diosmetin,1TBDMS,isomer #3COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O3556.7Semi standard non polar33892256
Diosmetin,2TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3656.5Semi standard non polar33892256
Diosmetin,2TBDMS,isomer #2COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3744.4Semi standard non polar33892256
Diosmetin,2TBDMS,isomer #3COC1=CC=C(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)C=C1O3767.6Semi standard non polar33892256
Diosmetin,3TBDMS,isomer #1COC1=CC=C(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)C=C1O[Si](C)(C)C(C)(C)C3897.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diosmetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kh9-0492000000-c9cb489c6e399645f54f2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diosmetin GC-MS (3 TMS) - 70eV, Positivesplash10-0ukc-2190860000-1029bf37ad921c9a81e82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diosmetin 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 - Diosmetin ESI-TOF 20V, Negative-QTOFsplash10-014u-0000700009-50048523dd30a3c691262017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 10V, Negative-QTOFsplash10-014u-0000700009-50048523dd30a3c691262017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 50V, Negative-QTOFsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 40V, Negative-QTOFsplash10-001i-0190000000-77edda567cd76512c52d2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 20V, Negative-QTOFsplash10-001i-0090000000-675379707ad9e98244a92017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 10V, Negative-QTOFsplash10-0002-0091000000-188fb9f96e76251ce5392017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 50V, Negative-QTOFsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin ESI-TOF 40V, Negative-QTOFsplash10-001i-0190000000-77edda567cd76512c52d2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-ITTOF , negative-QTOFsplash10-001i-0090000000-ae5188debe4910fab9c62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin Linear Ion Trap , negative-QTOFsplash10-001i-0090000000-6e1198f4157cda4df0ac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin Linear Ion Trap , negative-QTOFsplash10-001i-0090000000-b23157e3c53d703e88d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-675379707ad9e98244a92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOFsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOFsplash10-001i-0190000000-77edda567cd76512c52d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin Linear Ion Trap , positive-QTOFsplash10-000i-0094000000-0b3f48256d5c0ee7fb1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-QFT 21V, positive-QTOFsplash10-000i-0092000000-0448ee3b6390176e376a2020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin LC-ESI-IT 21V, positive-QTOFsplash10-000i-0090000000-8bb45858bd3dc65a5c072020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin 6V, Negative-QTOFsplash10-0002-0190000000-15ab8c66562248b310ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diosmetin 40V, Positive-QTOFsplash10-0a4i-0290000000-2ce24609e65e5b7d0d112021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 10V, Positive-QTOFsplash10-0udi-0009000000-a4a0986393c64d566f912015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 20V, Positive-QTOFsplash10-0udi-0019000000-9488c8767caac5f6b9b52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 40V, Positive-QTOFsplash10-0ufr-2590000000-e4455d0da36912d7b96a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 10V, Negative-QTOFsplash10-0002-0090000000-91f51b4b036d4731f3052015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 20V, Negative-QTOFsplash10-0002-0090000000-b6f4a2a03e7355f95b1c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosmetin 40V, Negative-QTOFsplash10-0ue9-0390000000-e296a45296f81b0f14542015-04-25Wishart 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 IDDB11259
Phenol Explorer Compound ID241
FooDB IDFDB000861
KNApSAcK IDC00001036
Chemspider ID4444931
KEGG Compound IDC10038
BioCyc IDCPD-20639
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
Good Scents IDrw1700891
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