2.0 2012-05-31 14:00:17 -0600 2015-06-03 15:54:32 -0600 ECMDB03791 M2MDB000523 3,4-Dihydroxyphenylacetaldehyde 3,4-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-Benzeneacetaldehyde Protocatechuatealdehyde C8H8O3 152.1473 152.047344122 2-(3,4-dihydroxyphenyl)acetaldehyde dopal 5707-55-1 OC1=C(O)C=C(CC=O)C=C1 InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2 IADQVXRMSNIUEL-UHFFFAOYSA-N Solid Extra-organism Periplasm logp 1.15 ALOGPS logs -1.24 ALOGPS solubility 8.72e+00 g/l ALOGPS logp 0.85 ChemAxon pka_strongest_acidic 9.27 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 2-(3,4-dihydroxyphenyl)acetaldehyde ChemAxon average_mass 152.1473 ChemAxon mono_mass 152.047344122 ChemAxon smiles OC1=C(O)C=C(CC=O)C=C1 ChemAxon formula C8H8O3 ChemAxon inchi InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2 ChemAxon inchikey IADQVXRMSNIUEL-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 40.4 ChemAxon polarizability 14.78 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tyrosine metabolism ec00350 Specdb::CMs 24620 Specdb::CMs 38654 Specdb::CMs 153813 Specdb::NmrOneD 34742 Specdb::NmrOneD 34743 Specdb::NmrOneD 34744 Specdb::NmrOneD 34745 Specdb::NmrOneD 34746 Specdb::NmrOneD 34747 Specdb::NmrOneD 34748 Specdb::NmrOneD 34749 Specdb::NmrOneD 34750 Specdb::NmrOneD 34751 Specdb::NmrOneD 34752 Specdb::NmrOneD 34753 Specdb::NmrOneD 34754 Specdb::NmrOneD 34755 Specdb::NmrOneD 34756 Specdb::NmrOneD 34757 Specdb::NmrOneD 34758 Specdb::NmrOneD 34759 Specdb::NmrOneD 34760 Specdb::NmrOneD 34761 Specdb::MsMs 19931 Specdb::MsMs 19932 Specdb::MsMs 19933 Specdb::MsMs 21482 Specdb::MsMs 21483 Specdb::MsMs 21484 Specdb::MsMs 2461312 Specdb::MsMs 2461313 Specdb::MsMs 2461314 Specdb::MsMs 2477363 Specdb::MsMs 2477364 Specdb::MsMs 2477365 HMDB03791 119219 106504 C04043 34-DIHYDROXYPHENYLACETALDEHYDE Keseler, 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. 21097882 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 Florang 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. 16956664 Marchitti 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. 17379813 Burke 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. 14697885 Burke 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. 11164826 Primary amine oxidase P46883 AMO_ECOLI tynA http://ecmdb.ca/proteins/P46883.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Dopamine + Water + Oxygen > 3,4-Dihydroxyphenylacetaldehyde + Hydrogen peroxide + Ammonium Dopamine + Water + Oxygen <> 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide R04300