2.02012-05-31 14:00:17 -06002015-06-03 15:54:32 -0600ECMDB03791M2MDB0005233,4-Dihydroxyphenylacetaldehyde3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids.3,4-Dihydroxy-BenzeneacetaldehydeProtocatechuatealdehydeC8H8O3152.1473152.0473441222-(3,4-dihydroxyphenyl)acetaldehydedopal5707-55-1OC1=C(O)C=C(CC=O)C=C1InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2IADQVXRMSNIUEL-UHFFFAOYSA-NSolidExtra-organismPeriplasmlogp1.15logs-1.24solubility8.72e+00 g/llogp0.85pka_strongest_acidic9.27pka_strongest_basic-6.3iupac2-(3,4-dihydroxyphenyl)acetaldehydeaverage_mass152.1473mono_mass152.047344122smilesOC1=C(O)C=C(CC=O)C=C1formulaC8H8O3inchiInChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2inchikeyIADQVXRMSNIUEL-UHFFFAOYSA-Npolar_surface_area57.53refractivity40.4polarizability14.78rotatable_bond_count2acceptor_count3donor_count2physiological_charge0formal_charge0Tyrosine metabolismec00350Specdb::CMs24620Specdb::CMs38654Specdb::CMs153813Specdb::NmrOneD34742Specdb::NmrOneD34743Specdb::NmrOneD34744Specdb::NmrOneD34745Specdb::NmrOneD34746Specdb::NmrOneD34747Specdb::NmrOneD34748Specdb::NmrOneD34749Specdb::NmrOneD34750Specdb::NmrOneD34751Specdb::NmrOneD34752Specdb::NmrOneD34753Specdb::NmrOneD34754Specdb::NmrOneD34755Specdb::NmrOneD34756Specdb::NmrOneD34757Specdb::NmrOneD34758Specdb::NmrOneD34759Specdb::NmrOneD34760Specdb::NmrOneD34761Specdb::MsMs19931Specdb::MsMs19932Specdb::MsMs19933Specdb::MsMs21482Specdb::MsMs21483Specdb::MsMs21484Specdb::MsMs2461312Specdb::MsMs2461313Specdb::MsMs2461314Specdb::MsMs2477363Specdb::MsMs2477364Specdb::MsMs2477365HMDB03791119219106504C0404334-DIHYDROXYPHENYLACETALDEHYDEKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, 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-D114.22080510Florang VR, Rees JN, Brogden NK, Anderson DG, Hurley TD, Doorn JA: Inhibition of the oxidative metabolism of 3,4-dihydroxyphenylacetaldehyde, a reactive intermediate of dopamine metabolism, by 4-hydroxy-2-nonenal. Neurotoxicology. 2007 Jan;28(1):76-82. Epub 2006 Aug 1.16956664Marchitti SA, Deitrich RA, Vasiliou V: Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase. Pharmacol Rev. 2007 Jun;59(2):125-50. Epub 2007 Mar 22.17379813Burke WJ, Li SW, Chung HD, Ruggiero DA, Kristal BS, Johnson EM, Lampe P, Kumar VB, Franko M, Williams EA, Zahm DS: Neurotoxicity of MAO metabolites of catecholamine neurotransmitters: role in neurodegenerative diseases. Neurotoxicology. 2004 Jan;25(1-2):101-15.14697885Burke WJ, Li SW, Zahm DS, Macarthur H, Kolo LL, Westfall TC, Anwar M, Glickstein SB, Ruggiero DA: Catecholamine monoamine oxidase a metabolite in adrenergic neurons is cytotoxic in vivo. Brain Res. 2001 Feb 9;891(1-2):218-27.11164826Primary amine oxidaseP46883AMO_ECOLItynAhttp://ecmdb.ca/proteins/P46883.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlDopamine + Water + Oxygen > 3,4-Dihydroxyphenylacetaldehyde + Hydrogen peroxide + AmmoniumDopamine + Water + Oxygen <> 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxideR04300