3,4-Dihydroxyphenylglycol

Common Name

3,4-Dihydroxyphenylglycol Description

3,4-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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (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 Formlia

C₈H₁₀O₄ Average Molecliar Weight

170.1626 Monoisotopic Molecliar Weight

170.057908808 IUPAC Name

4-(1,2-dihydroxyethyl)benzene-1,2-diol Traditional Name

3,4-dihydroxyphenylglycol CAS Registry Number

28822-73-3 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 Key

MTVWFVDWRVYDOR-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as catechols. These are compounds containing a 1,2-benzenediol moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Phenols Direct Parent

Catechols Alternative Parents

1-hydroxy-4-unsubstituted benzenoids

1-hydroxy-2-unsubstituted benzenoids

Benzene and substituted derivatives

Secondary alcohols

1,2-diols

Primary alcohols

Hydrocarbon derivatives

Aromatic alcohols

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

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

catechols (CHEBI:1387 )

tetrol (CHEBI:1387 )

a catechol (CPD-11878 )

Ontology Status

Detected and Quantified Origin

Endogenous

Biofunction

Not Available Application

Not Available Cellliar locations

Cytoplasm

Extracellliar

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point130 – 132 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-1.01HANSCH,C ET AL. (1995)

Predicted Properties

Property Value Source Water Solubility16.7 mg/mLALOGPS 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 Å²ChemAxon Rotatable Bond Count2ChemAxon Refractivity42.8 m³·mol^-1ChemAxon Polarizability16.57 Å³ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key GC-MS

GC-MS Spectrum – GC-MS (4 TMS)splash10-0a59-0965000000-0c949d05cfff1600a5dbView in MoNA GC-MS

GC-MS Spectrum – EI-Bsplash10-00y3-8900000000-0cb05419b964f5d6016bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00fr-2900000000-fbceba2f96c4ee1154aeView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-dd28ad7f56904a5c7c7eView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0bvi-9200000000-b9f4f1a5509344427d53View in MoNA LC-MS/MS

LC-MS/MS Spectrum – EI-B (HITACHI M-52) , Positivesplash10-00y3-8900000000-0cb05419b964f5d6016bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-0udi-0900000000-d656bf5821ba57e34cfaView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-00di-0900000000-785c9bdff21d7558b9b4View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0fk9-1900000000-953cf944dd232b8d7832View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0zg0-7900000000-cb8414fe82a1c814f764View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-014i-0900000000-a3cd8f79f0fba00900c3View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0aor-1900000000-ecff175233ea65fe5f8fView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4i-7900000000-f8265f1946f33cedd546View in MoNA 1D NMR

1H NMR SpectrumNot Available 2D NMR

[1H,13C] 2D NMR SpectrumNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Biofluid Locations

Blood

Cerebrospinal Fluid (CSF)

Urine

Tissue Location

Adrenal Medlila

Brain

Nerve Cells

Prostate

Pathways

Name SMPDB Link KEGG Link AlkaptonuriaSMP00169Not Available Dislifiram PathwaySMP00429Not Available Dopamine beta-hydroxylase deficiencySMP00498Not Available HawkinsinuriaSMP00190Not Available Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available Tyrosine MetabolismSMP00006map00350 Tyrosinemia Type ISMP00218Not Available Tyrosinemia, transient, of the newbornSMP00494Not Available

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.008 +/- 0.005 uMInfant (0-1 year old)Not SpecifiedNormal

18256395

details BloodDetected and Quantified0.006 +/- 0.0016 uMAdlit (>18 years old)BothNormal

6877032

details BloodDetected and Quantified0.009 +/- 0.003 uMNewborn (0-30 days old)BothNormal

18256395

details Cerebrospinal Fluid (CSF)Detected and Quantified0.204 +/- 0.0674 uMAdlit (>18 years old)Not SpecifiedNormal

3773351

details UrineDetected and Quantified0.25 umol/mmol creatinineAdlit (>18 years old)MaleNormal

Geigy Scientific …

details

Abnormal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.002 +/- 0.001 uMInfant (0-1 year old)Not SpecifiedMenkes syndrome

18256395

details BloodDetected and Quantified0.004 +/- 0.002 uMNewborn (0-30 days old)BothMenkes syndrome

18256395

details

Associated Disorders and Diseases Disease References

Menkes disease

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

309400 (Menkes disease)

External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

661 Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB020084 KNApSAcK ID

Not Available Chemspider ID

82648 KEGG Compound ID

C05576 BioCyc ID

Not Available BiGG ID

46054 Wikipedia Link

DHPG NuGOwiki Link

HMDB00318 Metagene Link

HMDB00318 METLIN ID

5307 PubChem Compound

91528 PDB ID

Not Available ChEBI ID

1387

Product: S49076

References Synthesis Reference Hunter 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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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