3,4-Dihydroxyphenylacetaldehyde (BioDeep_00000005383)

 

Secondary id: BioDeep_00001868755

human metabolite Endogenous


代谢物信息卡片


Dopal (3,4-Dihydroxyphenyl)acetaldehyde)

化学式: C8H8O3 (152.0473)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 8.74%

分子结构信息

SMILES: c1(c(ccc(c1)CC=O)O)O
InChI: InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2

描述信息

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. DOPAL generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. 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. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826, 16956664 [HMDB]. 3,4-Dihydroxyphenylacetaldehyde is found in many foods, some of which are asian pear, pak choy, papaya, and abiyuch.
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. DOPAL generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. 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. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826, 16956664.
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同义名列表

8 个代谢物同义名

Dopal (3,4-Dihydroxyphenyl)acetaldehyde); 2-(3,4-dihydroxyphenyl)acetaldehyde; 3,4-Dihydroxy-benzeneacetaldehyde; 3,4-Dihydroxyphenylacetaldehyde; 2-(3,4-Dihydroxyphenyl)ethanal; Protocatechuatealdehyde; DHPAA aldehyde; DOPAL



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

40 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(9)

WikiPathways(3)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(25)

PharmGKB(0)

3 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 15 ADH5, AKR1B1, ALDH1A1, ALDH1A2, AOC3, CASP3, CAT, DDC, GAPDH, HPGDS, HTT, PTGS2, SNCA, TH, TYR
Peripheral membrane protein 1 PTGS2
Endosome membrane 1 HTT
Endoplasmic reticulum membrane 1 PTGS2
Mitochondrion membrane 1 MAOA
Nucleus 5 CASP3, GAPDH, HTT, SNCA, TH
autophagosome 1 HTT
cytosol 15 ADH5, AKR1A1, AKR1B1, ALDH1A1, ALDH1A2, CASP3, CAT, DDC, GAPDH, HPGDS, HTT, MAOA, NGF, SNCA, TH
dendrite 4 HTT, NGF, SLC18A2, TH
centrosome 1 SLC18A2
nucleoplasm 4 AKR1B1, CASP3, HPGDS, HTT
Cell membrane 2 AOC3, HTT
Cytoplasmic side 1 MAOA
Cell projection, axon 4 ALDH1A1, SLC18A2, SNCA, TH
Multi-pass membrane protein 2 HTT, SLC18A2
Synapse 4 AKR1A1, ALDH1A1, HTT, SNCA
cell cortex 1 SNCA
cell surface 1 AOC3
glutamatergic synapse 1 CASP3
Golgi apparatus 2 AOC3, HTT
growth cone 1 SNCA
neuronal cell body 2 CASP3, SNCA
postsynapse 1 SNCA
presynaptic membrane 1 HTT
smooth endoplasmic reticulum 1 TH
synaptic vesicle 3 NGF, SLC18A2, TH
Cytoplasm, cytosol 3 AKR1A1, ALDH1A1, GAPDH
Lysosome 2 SNCA, TYR
plasma membrane 5 AOC3, GAPDH, HTT, SLC18A2, SNCA
synaptic vesicle membrane 2 SLC18A2, SNCA
terminal bouton 2 SLC18A2, TH
Membrane 6 AOC3, CAT, GAPDH, MAOA, SLC18A2, SNCA
apical plasma membrane 1 AKR1A1
axon 6 ALDH1A1, HTT, NGF, SLC18A2, SNCA, TH
caveola 1 PTGS2
extracellular exosome 8 ADH5, AKR1A1, AKR1B1, ALDH1A1, ALDH2, CAT, DDC, GAPDH
endoplasmic reticulum 3 AOC3, HTT, PTGS2
extracellular space 4 AKR1A1, AKR1B1, NGF, SNCA
perinuclear region of cytoplasm 6 ALDH1A2, GAPDH, HTT, SNCA, TH, TYR
mitochondrion 7 ADH5, AKR1B1, ALDH2, CAT, MAOA, SNCA, TH
protein-containing complex 4 CAT, HTT, PTGS2, SNCA
intracellular membrane-bounded organelle 5 CAT, GAPDH, HPGDS, SLC18A2, TYR
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TYR
Secreted 2 NGF, SNCA
extracellular region 3 CAT, NGF, SNCA
cytoplasmic side of plasma membrane 1 TH
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 1 MAOA
Mitochondrion matrix 1 ALDH2
mitochondrial matrix 2 ALDH2, CAT
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 SLC18A2
nuclear membrane 1 GAPDH
actin cytoskeleton 1 SNCA
perikaryon 1 TH
cytoplasmic vesicle 1 TH
microtubule cytoskeleton 1 GAPDH
Melanosome membrane 2 TH, TYR
Early endosome 2 AOC3, HTT
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 AOC3
vesicle 1 GAPDH
postsynaptic membrane 1 HTT
Apical cell membrane 1 AKR1A1
Cytoplasm, perinuclear region 2 GAPDH, TH
Membrane raft 1 HTT
Cell junction, focal adhesion 1 HTT
Cytoplasm, cytoskeleton 1 GAPDH
focal adhesion 2 CAT, HTT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 HTT
Cell projection, neuron projection 1 HTT
neuron projection 3 HTT, PTGS2, TH
supramolecular fiber 1 SNCA
cytoskeleton 1 GAPDH
centriole 1 HTT
Endomembrane system 1 HTT
endosome lumen 1 NGF
microvillus 1 AOC3
Lipid droplet 1 GAPDH
Cytoplasmic vesicle membrane 1 HTT
Cell projection, dendrite 1 SLC18A2
Melanosome 1 TYR
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
secretory granule membrane 1 SLC18A2
Golgi lumen 1 NGF
endoplasmic reticulum lumen 1 PTGS2
axon terminus 1 SNCA
Single-pass type IV membrane protein 1 MAOA
ribonucleoprotein complex 1 GAPDH
death-inducing signaling complex 1 CASP3
dopaminergic synapse 1 SLC18A2
Cytoplasmic vesicle, secretory vesicle membrane 1 SLC18A2
postsynaptic cytosol 1 HTT
GAIT complex 1 GAPDH
presynaptic cytosol 1 HTT
catalase complex 1 CAT
inclusion body 2 HTT, SNCA
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
clathrin-sculpted monoamine transport vesicle membrane 1 SLC18A2
serotonergic synapse 1 HTT
[Huntingtin]: Cytoplasm 1 HTT
[Huntingtin, myristoylated N-terminal fragment]: Cytoplasmic vesicle, autophagosome 1 HTT


文献列表

  • David S Goldstein. The catecholaldehyde hypothesis: where MAO fits in. Journal of neural transmission (Vienna, Austria : 1996). 2020 02; 127(2):169-177. doi: 10.1007/s00702-019-02106-9. [PMID: 31807952]
  • Vanderlei de Araújo Lima, Lucas Alex do Nascimento, David Eliezer, Cristian Follmer. Role of Parkinson's Disease-Linked Mutations and N-Terminal Acetylation on the Oligomerization of α-Synuclein Induced by 3,4-Dihydroxyphenylacetaldehyde. ACS chemical neuroscience. 2019 01; 10(1):690-703. doi: 10.1021/acschemneuro.8b00498. [PMID: 30352158]
  • Margaret-Ann M Nelson, Zachariah J Builta, T Blake Monroe, Jonathan A Doorn, Ethan J Anderson. Biochemical characterization of the catecholaldehyde reactivity of L-carnosine and its therapeutic potential in human myocardium. Amino acids. 2019 Jan; 51(1):97-102. doi: 10.1007/s00726-018-2647-y. [PMID: 30191330]
  • Jon W Werner-Allen, Rodney L Levine, Ad Bax. Superoxide is the critical driver of DOPAL autoxidation, lysyl adduct formation, and crosslinking of α-synuclein. Biochemical and biophysical research communications. 2017 May; 487(2):281-286. doi: 10.1016/j.bbrc.2017.04.050. [PMID: 28412346]
  • N Plotegher, G Berti, E Ferrari, I Tessari, M Zanetti, L Lunelli, E Greggio, M Bisaglia, M Veronesi, S Girotto, M Dalla Serra, C Perego, L Casella, L Bubacco. DOPAL derived alpha-synuclein oligomers impair synaptic vesicles physiological function. Scientific reports. 2017 01; 7(?):40699. doi: 10.1038/srep40699. [PMID: 28084443]
  • David G Anderson, Virginia R Florang, Josephine H Schamp, Garry R Buettner, Jonathan A Doorn. Antioxidant-Mediated Modulation of Protein Reactivity for 3,4-Dihydroxyphenylacetaldehyde, a Toxic Dopamine Metabolite. Chemical research in toxicology. 2016 07; 29(7):1098-107. doi: 10.1021/acs.chemrestox.5b00528. [PMID: 27268734]
  • Jon W Werner-Allen, Jenna F DuMond, Rodney L Levine, Ad Bax. Toxic Dopamine Metabolite DOPAL Forms an Unexpected Dicatechol Pyrrole Adduct with Lysines of α-Synuclein. Angewandte Chemie (International ed. in English). 2016 06; 55(26):7374-8. doi: 10.1002/anie.201600277. [PMID: 27158766]
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  • Cristian Follmer, Eduardo Coelho-Cerqueira, Danilo Y Yatabe-Franco, Gabriel D T Araujo, Anderson S Pinheiro, Gilberto B Domont, David Eliezer. Oligomerization and Membrane-binding Properties of Covalent Adducts Formed by the Interaction of α-Synuclein with the Toxic Dopamine Metabolite 3,4-Dihydroxyphenylacetaldehyde (DOPAL). The Journal of biological chemistry. 2015 Nov; 290(46):27660-79. doi: 10.1074/jbc.m115.686584. [PMID: 26381411]
  • David S Goldstein, Irwin J Kopin, Yehonatan Sharabi. Catecholamine autotoxicity. Implications for pharmacology and therapeutics of Parkinson disease and related disorders. Pharmacology & therapeutics. 2014 Dec; 144(3):268-82. doi: 10.1016/j.pharmthera.2014.06.006. [PMID: 24945828]
  • John E Casida, Breanna Ford, Yunden Jinsmaa, Patti Sullivan, Adele Cooney, David S Goldstein. Benomyl, aldehyde dehydrogenase, DOPAL, and the catecholaldehyde hypothesis for the pathogenesis of Parkinson's disease. Chemical research in toxicology. 2014 Aug; 27(8):1359-61. doi: 10.1021/tx5002223. [PMID: 25045800]
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