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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:51 UTC
HMDB IDHMDB0000318
Secondary Accession Numbers
  • HMDB0005870
  • HMDB00318
  • HMDB05870
Metabolite Identification
Common Name3,4-Dihydroxyphenylglycol
Description3,4-Dihydroxyphenylglycol, also known as DHPG or DOPEG, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxyphenylglycol is an extremely weak basic (essentially neutral) compound. 3,4-Dihydroxyphenylglycol exists in all living organisms, ranging from bacteria to plants to humans. It is a potent antioxidant (PMID: 30007612 ). In mammals, 3,4-Dihydroxyphenylglycol is the primary metabolite of norepinephrine and is generated through the action of the enzyme monoamine oxidase (MAO). DHPG is then further metabolized by the enzyme Catechol-O-methyltransferase (COMT) to 3-methoxy-4-hydroxyphenylglycol (MHPG). Within humans, 3,4-dihydroxyphenylglycol participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylglycol can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme alcohol dehydrogenase 1A. In addition, 3,4-dihydroxyphenylglycol and guaiacol can be converted into vanylglycol and pyrocatechol through its interaction with the enzyme catechol O-methyltransferase. Outside of the human body, 3,4-dihydroxyphenylglycol is found, on average, in the highest concentration in olives. High levels of DHPG (up to 368 mg/kg of dry weight) have been found in the pulp of natural black olives. This could make 3,4-dihydroxyphenylglycol a potential biomarker for the consumption of olives and olive oil. 3,4-Dihydroxyphenylglycol has been linked to Menkes disease (PMID: 19234788 ). DHPG level are lower in Menkes patients (3.57 ± 0.40 nM) than healthy infants 8.91 ± 0.77 nM). Menkes disease (also called “kinky hair disease”) is an X-linked recessive neurodevelopmental disorder caused by defects in a gene that encodes a copper-transporting ATPase (ATP7A). Affected infants typically appear healthy at birth and show normal neurodevelopment for 2-3 months. Subsequently there is loss of milestones (e.g., smiling, visual tracking, head control) and death in late infancy or childhood (PMID: 19234788 ).
Structure
Data?1582752123
Synonyms
ValueSource
(3,4-Dihydroxyphenyl)ethylene glycolChEBI
1-(3,4-Dihydroxyphenyl)-1,2-ethanediolChEBI
2-Hydroxy-2-(3,4-dihydroxy)phenylethanolChEBI
3,4-Dihydroxyphenethyl glycolChEBI
3,4-Dihydroxyphenylethyl glycolChEBI
beta,3,4-Trihydroxy phenethyl alcoholChEBI
DHPGChEBI
Dihydroxyphenylethylene glycolChEBI
DOPEGChEBI
b,3,4-Trihydroxy phenethyl alcoholGenerator
Β,3,4-trihydroxy phenethyl alcoholGenerator
3,4-DihydroxyphenylethyleneglycolHMDB
4-(1,2-Dihydroxyethyl)-1,2-benzenediolHMDB
DL-3,4-DihydroxyphenylglycolHMDB
Dihydroxyphenylethylene glycol, (+-)-isomerHMDB
Dihydroxyphenylethylene glycol, (S)-isomerHMDB
DihydroxyphenylglycineHMDB
Chemical FormulaC8H10O4
Average Molecular Weight170.1626
Monoisotopic Molecular Weight170.057908808
IUPAC Name4-(1,2-dihydroxyethyl)benzene-1,2-diol
Traditional Name3,4-dihydroxyphenylglycol
CAS Registry Number28822-73-3
SMILES
OCC(O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
InChI KeyMTVWFVDWRVYDOR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 132 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.01HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.7 g/LALOGPS
logP-0.72ALOGPS
logP-0.032ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.8 m³·mol⁻¹ChemAxon
Polarizability16.57 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]+137.63131661259
DarkChem[M-H]-133.48731661259
AllCCS[M+H]+137.91432859911
AllCCS[M-H]-134.16532859911
DeepCCS[M+H]+138.0930932474
DeepCCS[M-H]-134.33930932474
DeepCCS[M-2H]-171.95130932474
DeepCCS[M+Na]+147.48930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DihydroxyphenylglycolOCC(O)C1=CC(O)=C(O)C=C13293.2Standard polar33892256
3,4-DihydroxyphenylglycolOCC(O)C1=CC(O)=C(O)C=C11795.3Standard non polar33892256
3,4-DihydroxyphenylglycolOCC(O)C1=CC(O)=C(O)C=C11824.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxyphenylglycol,1TMS,isomer #1C[Si](C)(C)OCC(O)C1=CC=C(O)C(O)=C11916.3Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #2C[Si](C)(C)OC(CO)C1=CC=C(O)C(O)=C11893.8Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #3C[Si](C)(C)OC1=CC(C(O)CO)=CC=C1O1830.8Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O1851.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O)C(O)=C11858.4Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #2C[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C)C(O)=C11838.9Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #3C[Si](C)(C)OCC(O)C1=CC=C(O)C(O[Si](C)(C)C)=C11828.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C)C=C1O1815.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #5C[Si](C)(C)OC1=CC(C(CO)O[Si](C)(C)C)=CC=C1O1794.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O[Si](C)(C)C1855.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C11798.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #2C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C11804.3Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #3C[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11840.3Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C)C=C1O[Si](C)(C)C1822.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,4TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11824.3Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O)C(O)=C12138.4Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CO)C1=CC=C(O)C(O)=C12118.8Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C(O)CO)=CC=C1O2065.0Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O2092.4Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12352.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12318.6Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12302.7Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C(C)(C)C)C=C1O2289.9Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(C(CO)O[Si](C)(C)C(C)(C)C)=CC=C1O2277.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O[Si](C)(C)C(C)(C)C2338.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12506.5Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12505.2Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12539.9Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2513.2Semi standard non polar33892256
3,4-Dihydroxyphenylglycol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12732.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (4 TMS)splash10-0a59-0965000000-0c949d05cfff1600a5db2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxyphenylglycol EI-B (Non-derivatized)splash10-00y3-8900000000-0cb05419b964f5d6016b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized)splash10-0a59-0965000000-0c949d05cfff1600a5db2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-EI-TOF (Non-derivatized)splash10-0a4j-0936000000-6334bc60ea77682060ca2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ly9-2900000000-9512bd346f5c1a6474d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (4 TMS) - 70eV, Positivesplash10-0a4l-3009500000-7ac807311c5bfb441ee92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00fr-2900000000-fbceba2f96c4ee1154ae2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9300000000-dd28ad7f56904a5c7c7e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0bvi-9200000000-b9f4f1a5509344427d532012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol EI-B (HITACHI M-52) , Positive-QTOFsplash10-00y3-8900000000-0cb05419b964f5d6016b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol , negative-QTOFsplash10-0udi-0900000000-d656bf5821ba57e34cfa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 35V, Negative-QTOFsplash10-0uk9-0900000000-d35e76633f689d86ec712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 35V, Negative-QTOFsplash10-00di-0900000000-98bd90051b89e92f73832021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Positive-QTOFsplash10-00di-0900000000-785c9bdff21d7558b9b42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Positive-QTOFsplash10-0fk9-1900000000-953cf944dd232b8d78322015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Positive-QTOFsplash10-0zg0-7900000000-cb8414fe82a1c814f7642015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Negative-QTOFsplash10-014i-0900000000-a3cd8f79f0fba00900c32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Negative-QTOFsplash10-0aor-1900000000-ecff175233ea65fe5f8f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Negative-QTOFsplash10-0a4i-7900000000-f8265f1946f33cedd5462015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Negative-QTOFsplash10-0gb9-0900000000-e314b75f5fe1649a113b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Negative-QTOFsplash10-0fl0-0900000000-1e4c5e4e19625ce535722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Negative-QTOFsplash10-052f-9400000000-637155f483cd289f34ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Positive-QTOFsplash10-000i-0900000000-73931a09199f234b44b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Positive-QTOFsplash10-0nmr-3900000000-563a89742bb8d15cecc42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Positive-QTOFsplash10-0ue9-9100000000-5934a8f5824689891a5d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adrenal Medulla
  • Brain
  • Neuron
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.005 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.006 +/- 0.0016 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.009 +/- 0.003 uMNewborn (0-30 days old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.204 +/- 0.0674 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.25 umol/mmol creatinineAdult (>18 years old)MaleNormal
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details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.002 +/- 0.001 uMInfant (0-1 year old)Not SpecifiedMenkes syndrome details
BloodDetected and Quantified0.004 +/- 0.002 uMNewborn (0-30 days old)BothMenkes syndrome details
Associated Disorders and Diseases
Disease References
Menkes disease
  1. Kaler SG, Holmes CS, Goldstein DS, Tang J, Godwin SC, Donsante A, Liew CJ, Sato S, Patronas N: Neonatal diagnosis and treatment of Menkes disease. N Engl J Med. 2008 Feb 7;358(6):605-14. doi: 10.1056/NEJMoa070613. [PubMed:18256395 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID661
FooDB IDFDB020084
KNApSAcK IDNot Available
Chemspider ID82648
KEGG Compound IDC05576
BioCyc IDCPD-11878
BiGG ID46054
Wikipedia LinkNot Available
METLIN ID5307
PubChem Compound91528
PDB IDNot Available
ChEBI ID1387
Food Biomarker OntologyNot Available
VMH ID34DHOXPEG
MarkerDB IDMDB00000143
Good Scents IDNot Available
References
Synthesis ReferenceHunter L W; Rorie D K; Yaksh T L; Tyce G M Concurrent separation of catecholamines, dihydroxyphenylglycol, vasoactive intestinal peptide, and neuropeptide Y in superfusate and tissue extract. Analytical biochemistry (1988), 173(2), 340-52.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Julien C, Rodriguez C, Sacquet J, Cuisinaud G, Sassard J: Liquid-chromatographic determination of free and total 3,4-dihydroxyphenylglycol and 3-methoxy-4-hydroxyphenylglycol in urine. Clin Chem. 1988 May;34(5):966-9. [PubMed:3370800 ]
  3. Nakada T, Sasagawa I, Kubota Y, Suzuki H, Ishigooka M, Watanabe M: Dihydroxyphenylglycol in pheochromocytoma: its diagnostic use for norepinephrine dominant tumor. J Urol. 1996 Jan;155(1):14-8. [PubMed:7490813 ]
  4. Eisenhofer G, Brush JE, Cannon RO 3rd, Stull R, Kopin IJ, Goldstein DS: Plasma dihydroxyphenylalanine and total body and regional noradrenergic activity in humans. J Clin Endocrinol Metab. 1989 Feb;68(2):247-55. [PubMed:2563731 ]
  5. Divers WA Jr, Wilkes MM, Babaknia A, Yen SS: Maternal smoking and elevation of catecholamines and metabolites in the amniotic fluid. Am J Obstet Gynecol. 1981 Nov 15;141(6):625-8. [PubMed:7315891 ]
  6. Graham PE, Smythe GA, Edwards GA, Lazarus L: Laboratory diagnosis of phaeochromocytoma: which analytes should we measure? Ann Clin Biochem. 1993 Mar;30 ( Pt 2):129-34. [PubMed:8466142 ]
  7. Machida M, Sakaguchi A, Kamada S, Fujimoto T, Takechi S, Kakinoki S, Nomura A: Simultaneous analysis of human plasma catecholamines by high-performance liquid chromatography with a reversed-phase triacontylsilyl silica column. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 18;830(2):249-54. Epub 2005 Nov 21. [PubMed:16301006 ]
  8. Eisenhofer G, Kopin IJ, Goldstein DS: Catecholamine metabolism: a contemporary view with implications for physiology and medicine. Pharmacol Rev. 2004 Sep;56(3):331-49. [PubMed:15317907 ]
  9. Baskys A, Fang L, Bayazitov I: Activation of neuroprotective pathways by metabotropic group I glutamate receptors: a potential target for drug discovery? Ann N Y Acad Sci. 2005 Aug;1053:55-73. [PubMed:16179509 ]
  10. Esler MD, Lambert GW, Ferrier C, Kaye DM, Wallin BG, Kalff V, Kelly MJ, Jennings GL: Central nervous system noradrenergic control of sympathetic outflow in normotensive and hypertensive humans. Clin Exp Hypertens. 1995 Jan-Feb;17(1-2):409-23. [PubMed:7735286 ]
  11. Divers WA, Wilkes MM, Babaknia A, Hill LM, Quilligan EJ, Yen SS: Amniotic fluid catecholamines and metabolites in intrauterine growth retardation. Am J Obstet Gynecol. 1981 Nov 15;141(6):608-10. [PubMed:7315888 ]
  12. Elsworth JD, Roth RH, Redmond DE Jr: Relative importance of 3-methoxy-4-hydroxyphenylglycol and 3,4-dihydroxyphenylglycol as norepinephrine metabolites in rat, monkey, and humans. J Neurochem. 1983 Sep;41(3):786-93. [PubMed:6875564 ]
  13. Loo H, Scatton B, Dennis T, Benkelfat C, Gay C, Poirier-Littre MF, Garreau M, Vanelle JM, Olie JP, Deniker P: [Study of noradrenaline metabolism in depressed patients by the determination of plasma dihydroxyphenylethylene glycol]. Encephale. 1983;9(4):297-316. [PubMed:6671452 ]
  14. Bermudez-Oria A, Rodriguez-Gutierrez G, Rodriguez-Juan E, Gonzalez-Benjumea A, Fernandez-Bolanos J: Molecular interactions between 3,4-dihydroxyphenylglycol and pectin and antioxidant capacity of this complex in vitro. Carbohydr Polym. 2018 Oct 1;197:260-268. doi: 10.1016/j.carbpol.2018.05.089. Epub 2018 May 31. [PubMed:30007612 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxyphenylglycol → S-Adenosylhomocysteine + Vanylglycoldetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27
Reactions
3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Iondetails