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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:20:37 UTC
HMDB IDHMDB0000318
Secondary Accession Numbers
  • HMDB00318
  • HMDB05870
Metabolite Identification
Common Name3,4-Dihydroxyphenylglycol
Description3,4-Dihydroxyphenylglycol (DOPEG) is a normal norepinephrine metabolite present in CSF, plasma and urine in humans (PMID 6875564 ). In healthy individuals there is a tendency for free DOPEG to increase and for conjugated DOPEG to decrease with age; plasmatic DOPEG levels are significantly lower in depressed patients as compared to healthy controls (PMID 6671452 ).
Structure
Thumb
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, (+-)-isomerMeSH
Dihydroxyphenylethylene glycol, (S)-isomerMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as catechols. These are compounds containing a 1,2-benzenediol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

    Cell:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 - 132 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.01HANSCH,C ET AL. (1995)
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0a59-0965000000-0c949d05cfff1600a5dbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00y3-8900000000-0cb05419b964f5d6016bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a59-0965000000-0c949d05cfff1600a5dbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0936000000-6334bc60ea77682060caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ly9-2900000000-9512bd346f5c1a6474d1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4l-3009500000-7ac807311c5bfb441ee9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00fr-2900000000-fbceba2f96c4ee1154aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-dd28ad7f56904a5c7c7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bvi-9200000000-b9f4f1a5509344427d53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00y3-8900000000-0cb05419b964f5d6016bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-d656bf5821ba57e34cfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-785c9bdff21d7558b9b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-1900000000-953cf944dd232b8d7832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg0-7900000000-cb8414fe82a1c814f764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a3cd8f79f0fba00900c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1900000000-ecff175233ea65fe5f8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-f8265f1946f33cedd546View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Medulla
  • Brain
  • Nerve Cells
  • Prostate
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaPw000180Pw000180 greyscalePw000180 simpleNot Available
Disulfiram PathwayPw000431Pw000431 greyscalePw000431 simpleNot Available
Dopamine beta-hydroxylase deficiencyPw000474Pw000474 greyscalePw000474 simpleNot Available
HawkinsinuriaPw000181Pw000181 greyscalePw000181 simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)Pw000509Pw000509 greyscalePw000509 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 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 and Quantified0.25 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID661
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB020084
KNApSAcK IDNot Available
Chemspider ID82648
KEGG Compound IDC05576
BioCyc IDNot Available
BiGG ID46054
Wikipedia LinkDHPG
METLIN ID5307
PubChem Compound91528
PDB IDNot Available
ChEBI ID1387
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 ]

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