2.0 2012-05-31 10:26:21 -0600 2015-09-13 12:56:07 -0600 ECMDB00318 M2MDB000131 3,4-Dihydroxyphenylglycol (S)-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group metabotropic glutamate receptors (mGluRs). It is an intermediate in tyrosine metabolism. (3,4-Dihydroxyphenyl)ethylene glycol 1-(3,4-Dihydroxyphenyl)-1,2-ethanediol 3,4-Dihydroxyphenethyl glycol 3,4-Dihydroxyphenylethyl glycol 3,4-Dihydroxyphenylethyleneglycol 4-(1,2-Dihydroxyethyl)-1,2-benzenediol DHPG DL-3,4-Dihydroxyphenylglycol DOPEG C8H10O4 170.1626 170.057908808 4-(1,2-dihydroxyethyl)benzene-1,2-diol 3,4-dihydroxyphenylglycol 28822-73-3 OCC(O)C1=CC(O)=C(O)C=C1 InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2 MTVWFVDWRVYDOR-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.72 ALOGPS logs -1.01 ALOGPS solubility 1.67e+01 g/l ALOGPS melting_point 130-132 oC logp -0.032 ChemAxon pka_strongest_acidic 9.21 ChemAxon pka_strongest_basic -3 ChemAxon iupac 4-(1,2-dihydroxyethyl)benzene-1,2-diol ChemAxon average_mass 170.1626 ChemAxon mono_mass 170.057908808 ChemAxon smiles OCC(O)C1=CC(O)=C(O)C=C1 ChemAxon formula C8H10O4 ChemAxon inchi InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2 ChemAxon inchikey MTVWFVDWRVYDOR-UHFFFAOYSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 42.8 ChemAxon polarizability 16.57 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tyrosine metabolism ec00350 Specdb::CMs 1559 Specdb::CMs 26623 Specdb::CMs 27176 Specdb::CMs 31124 Specdb::CMs 32129 Specdb::CMs 37426 Specdb::CMs 149204 Specdb::CMs 1058139 Specdb::CMs 1058141 Specdb::CMs 1058142 Specdb::CMs 1058144 Specdb::CMs 1058146 Specdb::CMs 1058148 Specdb::CMs 1058149 Specdb::CMs 1058151 Specdb::CMs 1058153 Specdb::CMs 1058155 Specdb::CMs 1058157 Specdb::CMs 1058158 Specdb::CMs 1058160 Specdb::CMs 1058162 Specdb::CMs 1058163 Specdb::CMs 1058165 Specdb::CMs 1058167 Specdb::CMs 1058169 Specdb::NmrOneD 1329 Specdb::NmrOneD 6582 Specdb::NmrOneD 6583 Specdb::NmrOneD 6584 Specdb::NmrOneD 6585 Specdb::NmrOneD 6586 Specdb::NmrOneD 6587 Specdb::NmrOneD 6588 Specdb::NmrOneD 6589 Specdb::NmrOneD 6590 Specdb::NmrOneD 6591 Specdb::NmrOneD 6592 Specdb::NmrOneD 6593 Specdb::NmrOneD 6594 Specdb::NmrOneD 6595 Specdb::NmrOneD 6596 Specdb::NmrOneD 6597 Specdb::NmrOneD 6598 Specdb::NmrOneD 6599 Specdb::NmrOneD 6600 Specdb::NmrOneD 6601 Specdb::MsMs 531 Specdb::MsMs 532 Specdb::MsMs 533 Specdb::MsMs 4020 Specdb::MsMs 12797 Specdb::MsMs 12798 Specdb::MsMs 12799 Specdb::MsMs 19469 Specdb::MsMs 19470 Specdb::MsMs 19471 Specdb::MsMs 440123 Specdb::MsMs 2233968 Specdb::MsMs 2234991 Specdb::MsMs 2694846 Specdb::MsMs 2694847 Specdb::MsMs 2694848 Specdb::MsMs 2987747 Specdb::MsMs 2987748 Specdb::MsMs 2987749 Specdb::NmrTwoD 1272 HMDB00318 91528 82648 C05576 DHPG Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 6671452 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. http://hmdb.ca/system/metabolites/msds/000/000/237/original/HMDB00318.pdf?1358461228 Aldehyde-alcohol dehydrogenase P0A9Q7 ADHE_ECOLI adhE http://ecmdb.ca/proteins/P0A9Q7.xml S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml Alcohol dehydrogenase, propanol-preferring P39451 ADHP_ECOLI adhP http://ecmdb.ca/proteins/P39451.xml predicted Fe-containing alcohol dehydrogenase, Pfam00465 family P37686 yiaY http://ecmdb.ca/proteins/P37686.xml 3,4-Dihydroxyphenylglycol + NAD <> 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen ion R04880