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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:41 UTC
Update Date2020-09-15 23:41:48 UTC
HMDB IDHMDB0059966
Secondary Accession Numbers
  • HMDB59966
Metabolite Identification
Common Name3,5-Dimethoxyphenol
Description3,5-Dimethoxyphenol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3,5-Dimethoxyphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-Dimethoxyphenol has been detected, but not quantified in, several different foods, such as cumins, white lupines, common salsifies, dates, and herbs and spices. This could make 3,5-dimethoxyphenol a potential biomarker for the consumption of these foods. In such a case, the intoxication can be signalized by the presence of 3,5-dimethoxyphenol in biological material (PMID: 20942244 ). Autopsy findings of fatal intoxication with yew are nonspecific. If yew decoction is consumed, plant residues are not found. A presence of plant residues in the digestive tract can signalize yew intoxication. 3,5-Dimethoxyphenol is a toxin metabolite that can be found in human consuming yew (Taxus baccata) leaves.
Structure
Data?1600213308
Synonyms
ValueSource
35-DimethoxyphenolHMDB
1,3-Dimethoxy-5-hydroxybenzeneHMDB
Phloroglucinol dimethyl etherHMDB
PhloroglucindimethyletherHMDB
1-Hydroxy-3,5-dimethoxybenzeneHMDB
3,5-DimethoxyphenolHMDB
TaxicatigeninHMDB
Chemical FormulaC8H10O3
Average Molecular Weight154.1632
Monoisotopic Molecular Weight154.062994186
IUPAC Name3,5-dimethoxyphenol
Traditional Name3,5-dimethoxyphenol
CAS Registry Number500-99-2
SMILES
COC1=CC(OC)=CC(O)=C1
InChI Identifier
InChI=1S/C8H10O3/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5,9H,1-2H3
InChI KeyXQDNFAMOIPNVES-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.3 g/LALOGPS
logP10(1.27) g/LALOGPS
logP10(1.35) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.97 m³·mol⁻¹ChemAxon
Polarizability15.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.08731661259
DarkChem[M-H]-133.13331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5-DimethoxyphenolCOC1=CC(OC)=CC(O)=C12780.0Standard polar33892256
3,5-DimethoxyphenolCOC1=CC(OC)=CC(O)=C11393.3Standard non polar33892256
3,5-DimethoxyphenolCOC1=CC(OC)=CC(O)=C11464.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5-Dimethoxyphenol,1TMS,isomer #1COC1=CC(OC)=CC(O[Si](C)(C)C)=C11495.2Semi standard non polar33892256
3,5-Dimethoxyphenol,1TBDMS,isomer #1COC1=CC(OC)=CC(O[Si](C)(C)C(C)(C)C)=C11734.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-6ffc61bab3cb0daf06a42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dimethoxyphenol GC-MS (1 TMS) - 70eV, Positivesplash10-03k9-7970000000-5fec4139089a0e2011a52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dimethoxyphenol 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 - 3,5-Dimethoxyphenol 40V, Positive-QTOFsplash10-00kb-9000000000-dd3b3735bcca8e69a6302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOFsplash10-052b-7900000000-eacd2590827ce881ca002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOFsplash10-0a4i-0900000000-06b711f0dc96bdfc56732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOFsplash10-06r2-6900000000-62834705b287ef331bdb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOFsplash10-0a4i-0900000000-cbb9850ac89acafe6fef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Positive-QTOFsplash10-066s-9000000000-7e6892e595be5d70e9ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Negative-QTOFsplash10-052s-4900000000-61963bee977e4ea4b9962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Negative-QTOFsplash10-000i-0900000000-8ea3f0e77e96fb0968d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Negative-QTOFsplash10-0f6t-9000000000-35d5e5055c7b6adcf6d42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOFsplash10-0a4i-0900000000-ffd8ef068282d660a5a62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOFsplash10-0a4i-0900000000-531fc72bb729b51b93532015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Positive-QTOFsplash10-0abc-9800000000-81c47001436a795750102015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Negative-QTOFsplash10-0udi-0900000000-f4547a36e0b6f212d68c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Negative-QTOFsplash10-0udi-1900000000-90b6b285e82384859fd52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Negative-QTOFsplash10-0a4i-9600000000-c7ac2ee075cdab19e48d2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.421 +/- 0.081 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030390
KNApSAcK IDNot Available
Chemspider ID9954
KEGG Compound IDNot Available
BioCyc IDCPD-9499
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10383
PDB IDNot Available
ChEBI IDNot Available
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. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]
  2. Stribrny J, Dogosi M, Snuparek Z, Toupalik P, Balaz P, Bartos P: [3,5-dimethoxyfenol--marker intoxication with Taxus baccata]. Soud Lek. 2010 Jul;55(3):36-9. [PubMed:20942244 ]