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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-12 03:34:50 UTC
Update Date2023-02-21 17:28:55 UTC
HMDB IDHMDB0041662
Secondary Accession Numbers
  • HMDB41662
Metabolite Identification
Common Name3,4-O-Dimethylgallic acid
Description3,4-O-Dimethylgallic acid, also known as 3,4-O-dimethylgallate or DMHBA, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Based on a literature review very few articles have been published on 3,4-O-Dimethylgallic acid.
Structure
Data?1677000535
Synonyms
ValueSource
3,4-O-DimethylgallateGenerator
DMHBAHMDB
3,4-Dimethoxy-5-hydroxybenzoic acidHMDB
3-Hydroxy-4,5-dimethoxybenzoateHMDB
3,4-dimethoxygallic acid HMDB
3,4-O-dimethylgallic acidHMDB
5-hydroxyveratric acidHMDB
3-hydroxy-4,5-dimethoxybenzoic acidHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
IUPAC Name3-hydroxy-4,5-dimethoxybenzoic acid
Traditional Name3-hydroxy-4,5-dimethoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(O)=C1OC)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c1-13-7-4-5(9(11)12)3-6(10)8(7)14-2/h3-4,10H,1-2H3,(H,11,12)
InChI KeyWFIBQVFJXGQICQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGallic acid and derivatives
Alternative Parents
Substituents
  • Gallic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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 Solubility3.63 g/LALOGPS
logP1.38ALOGPS
logP1.01ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.7631661259
DarkChem[M-H]-143.22131661259
DeepCCS[M+H]+142.50530932474
DeepCCS[M-H]-138.67730932474
DeepCCS[M-2H]-176.06930932474
DeepCCS[M+Na]+151.60730932474
AllCCS[M+H]+142.932859911
AllCCS[M+H-H2O]+138.832859911
AllCCS[M+NH4]+146.732859911
AllCCS[M+Na]+147.832859911
AllCCS[M-H]-140.432859911
AllCCS[M+Na-2H]-141.032859911
AllCCS[M+HCOO]-141.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-O-Dimethylgallic acidCOC1=CC(=CC(O)=C1OC)C(O)=O2917.4Standard polar33892256
3,4-O-Dimethylgallic acidCOC1=CC(=CC(O)=C1OC)C(O)=O1730.5Standard non polar33892256
3,4-O-Dimethylgallic acidCOC1=CC(=CC(O)=C1OC)C(O)=O1747.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-O-Dimethylgallic acid,1TMS,isomer #1COC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1OC1807.6Semi standard non polar33892256
3,4-O-Dimethylgallic acid,1TMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1OC1797.3Semi standard non polar33892256
3,4-O-Dimethylgallic acid,2TMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1OC1850.1Semi standard non polar33892256
3,4-O-Dimethylgallic acid,1TBDMS,isomer #1COC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1OC2083.7Semi standard non polar33892256
3,4-O-Dimethylgallic acid,1TBDMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1OC2062.2Semi standard non polar33892256
3,4-O-Dimethylgallic acid,2TBDMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1OC2325.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-O-Dimethylgallic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-0900000000-4c88963fef853a8d6a652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-O-Dimethylgallic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-8196000000-295d89fc94fced912e902017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-O-Dimethylgallic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 10V, Positive-QTOFsplash10-000t-0900000000-fb8ffe24b52003300a382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 20V, Positive-QTOFsplash10-0f89-0900000000-6ed0ed507f79965e9e952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 40V, Positive-QTOFsplash10-0ka9-2900000000-40fab205158bb32d3d752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 10V, Negative-QTOFsplash10-0002-0900000000-7e148cea6e2951fe15972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 20V, Negative-QTOFsplash10-0f6t-0900000000-230215d59f169e7ad1892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 40V, Negative-QTOFsplash10-0pka-6900000000-47804112f400a698774d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 10V, Positive-QTOFsplash10-001i-0900000000-45e2c399f043e558b3952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 20V, Positive-QTOFsplash10-0f8a-0900000000-70780eccb2a1118c336b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 40V, Positive-QTOFsplash10-005i-9400000000-9b24691858311719f1422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 10V, Negative-QTOFsplash10-0002-0900000000-d50a53f419188a4061a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 20V, Negative-QTOFsplash10-0f6t-0900000000-3eb139913997c78ff7d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-O-Dimethylgallic acid 40V, Negative-QTOFsplash10-053r-9200000000-02e70d7f8b96a007eb452021-09-22Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.018 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.016 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.072 +/- 0.062 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.036 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.025 +/- 0.009 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.05 +/- 0.014 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.066 +/- 0.023 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.017 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 924 details
UrineDetected and Quantified0.057 +/- 0.011 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029820
KNApSAcK IDNot Available
Chemspider ID67282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74709
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. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]