3,4-dihydroxyphenylacetic acid (BioDeep_00000229588)
Main id: BioDeep_00000000447
human metabolite PANOMIX_OTCML-2023 BioNovoGene_Lab2019
代谢物信息卡片
3,4-dihydroxyphenylacetic acid
化学式: C8H8O4 (168.0423)
中文名称: 3,4-二羟基苯乙酸, 二羟苯乙酸(DOPAC)
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=C(C=C1CC(=O)O)O)O
InChI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
描述信息
3,4-Dihydroxybenzeneacetic acid is the main neuronal metabolite of dopamine.
同义名列表
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:41941
- KEGG: C01161
- PubChem: 547
- HMDB: HMDB01336
- DrugBank: DB01702
- ChEMBL: CHEMBL1284
- MeSH: 3,4-Dihydroxyphenylacetic Acid
- CAS: 102-32-9
- ChEBI: CHEBI:17612
- PubChem: 4388
- KNApSAcK: C00040996
- PDB-CCD: DHY
- 3DMET: B00250
- NIKKAJI: J804D
- medchemexpress: HY-W001080
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-876
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-436
- KNApSAcK: 17612
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
10 个相关的物种来源信息
- 3702 - Arabidopsis thaliana: 10.1111/TPJ.14594
- 392618 - Cunila: 10.1007/S00299-018-2303-8
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 102784 - Liatris elegans: 10.1080/14786410903027789
- 4146 - Olea europaea:
- 52852 - Secamone afzelii: 10.5586/ASBP.1998.029
- 261649 - Tragopogon orientalis: 10.5586/ASBP.1988.009
- 41653 - Tragopogon pratensis: 10.5586/ASBP.1988.009
- 51239 - Vanilla planifolia: 10.1021/JF010425K
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。
文献列表
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Molecular nutrition & food research.
2022 04; 66(8):e2100853. doi:
10.1002/mnfr.202100853. [PMID: 35112478] - Kyle C Chesler, Cara T Motz, Katie L Bales, Rachael A Allen, Harrison K Vo, Machelle T Pardue. Voluntary oral dosing for precise experimental compound delivery in adult rats.
Laboratory animals.
2022 Apr; 56(2):147-156. doi:
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2016 Apr; 182(?):190-9. doi:
10.1016/j.jep.2016.02.001. [PMID: 26899441] - Natalie Hirth, Marcus W Meinhardt, Hamid R Noori, Humberto Salgado, Oswaldo Torres-Ramirez, Stefanie Uhrig, Laura Broccoli, Valentina Vengeliene, Martin Roßmanith, Stéphanie Perreau-Lenz, Georg Köhr, Wolfgang H Sommer, Rainer Spanagel, Anita C Hansson. Convergent evidence from alcohol-dependent humans and rats for a hyperdopaminergic state in protracted abstinence.
Proceedings of the National Academy of Sciences of the United States of America.
2016 Mar; 113(11):3024-9. doi:
10.1073/pnas.1506012113. [PMID: 26903621] - Nicoletta Plotegher, Luigi Bubacco. Lysines, Achilles' heel in alpha-synuclein conversion to a deadly neuronal endotoxin.
Ageing research reviews.
2016 Mar; 26(?):62-71. doi:
10.1016/j.arr.2015.12.002. [PMID: 26690800] - Bonnie L Robinson, Melanie Dumas, Elvis Cuevas, Qiang Gu, Merle G Paule, Syed F Ali, Jyotshna Kanungo. Distinct effects of ketamine and acetyl L-carnitine on the dopamine system in zebrafish.
Neurotoxicology and teratology.
2016 Mar; 54(?):52-60. doi:
10.1016/j.ntt.2016.02.004. [PMID: 26898327] - Bryan A Killinger, Anna Moszczynska. Epothilone D prevents binge methamphetamine-mediated loss of striatal dopaminergic markers.
Journal of neurochemistry.
2016 Feb; 136(3):510-25. doi:
10.1111/jnc.13391. [PMID: 26465779] - Lucyna Konieczna, Anna Roszkowska, Maciej Niedźwiecki, Tomasz Bączek. Hydrophilic interaction chromatography combined with dispersive liquid-liquid microextraction as a preconcentration tool for the simultaneous determination of the panel of underivatized neurotransmitters in human urine samples.
Journal of chromatography. A.
2016 Jan; 1431(?):111-121. doi:
10.1016/j.chroma.2015.12.062. [PMID: 26747692] - Carla Patrícia Bejo Wolkers, Mônica Serra, Elisabeth Criscuolo Urbinati. Social challenge increases cortisol and hypothalamic monoamine levels in matrinxã (Brycon amazonicus).
Fish physiology and biochemistry.
2015 Dec; 41(6):1501-8. doi:
10.1007/s10695-015-0102-5. [PMID: 26205527] - 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] - Nadhir Litim, Mélanie Bourque, Sara Al Sweidi, Marc Morissette, Thérèse Di Paolo. The 5α-reductase inhibitor Dutasteride but not Finasteride protects dopamine neurons in the MPTP mouse model of Parkinson's disease.
Neuropharmacology.
2015 Oct; 97(?):86-94. doi:
10.1016/j.neuropharm.2015.05.015. [PMID: 26006269] - Sheng Chen, Xiao-Jie Zhang, Wen-Jie Xie, Hong-Yan Qiu, Hui Liu, Wei-Dong Le. A New VMAT-2 Inhibitor NBI-641449 in the Treatment of Huntington Disease.
CNS neuroscience & therapeutics.
2015 Aug; 21(8):662-71. doi:
10.1111/cns.12425. [PMID: 26122704] - Xiaoqi Pan, Xiongxiong Guo, Fei Xiong, Guihong Cheng, Qing Lu, Hong Yan. Acrylamide increases dopamine levels by affecting dopamine transport and metabolism related genes in the striatal dopaminergic system.
Toxicology letters.
2015 Jul; 236(1):60-8. doi:
10.1016/j.toxlet.2015.04.017. [PMID: 25943760] - Catalina Carrasco-Pozo, Martin Gotteland, Rodrigo L Castillo, Chen Chen. 3,4-Dihydroxyphenylacetic acid, a microbiota-derived metabolite of quercetin, protects against pancreatic β-cells dysfunction induced by high cholesterol.
Experimental cell research.
2015 Jun; 334(2):270-82. doi:
10.1016/j.yexcr.2015.03.021. [PMID: 25845496] - Xiaoting Yang, Yufei Hu, Gongke Li, Zhuomin Zhang. Acrylamide-functionalized graphene micro-solid-phase extraction coupled to high-performance liquid chromatography for the online analysis of trace monoamine acidic metabolites in biological samples.
Journal of separation science.
2015 May; 38(8):1380-7. doi:
10.1002/jssc.201401432. [PMID: 25655072] - Eduard Bentea, Michelle D Sconce, Madeline J Churchill, Joeri Van Liefferinge, Hideyo Sato, Charles K Meshul, Ann Massie. MPTP-induced parkinsonism in mice alters striatal and nigral xCT expression but is unaffected by the genetic loss of xCT.
Neuroscience letters.
2015 Apr; 593(?):1-6. doi:
10.1016/j.neulet.2015.03.013. [PMID: 25766755] - Lucy G Chastain, Hongyan Qu, Chase H Bourke, P Michael Iuvone, Paul R Dobner, Charles B Nemeroff, Becky Kinkead. Striatal dopamine receptor plasticity in neurotensin deficient mice.
Behavioural brain research.
2015 Mar; 280(?):160-71. doi:
10.1016/j.bbr.2014.11.014. [PMID: 25449842] - Caroline G M de Theije, Lieke W J van den Elsen, Linette E M Willemsen, Vanja Milosevic, Gerdien A H Korte-Bouws, Sofia Lopes da Silva, Laus M Broersen, S Mechiel Korte, Berend Olivier, Johan Garssen, Aletta D Kraneveld. Dietary long chain n-3 polyunsaturated fatty acids prevent impaired social behaviour and normalize brain dopamine levels in food allergic mice.
Neuropharmacology.
2015 Mar; 90(?):15-22. doi:
10.1016/j.neuropharm.2014.11.001. [PMID: 25445491] - S T Masoud, L M Vecchio, Y Bergeron, M M Hossain, L T Nguyen, M K Bermejo, B Kile, T D Sotnikova, W B Siesser, R R Gainetdinov, R M Wightman, M G Caron, J R Richardson, G W Miller, A J Ramsey, M Cyr, A Salahpour. Increased expression of the dopamine transporter leads to loss of dopamine neurons, oxidative stress and l-DOPA reversible motor deficits.
Neurobiology of disease.
2015 Feb; 74(?):66-75. doi:
10.1016/j.nbd.2014.10.016. [PMID: 25447236] - David S Goldstein, Irwin J Kopin, Yehonatan Sharabi, Courtney Holmes. Plasma biomarkers of decreased vesicular storage distinguish Parkinson disease with orthostatic hypotension from the parkinsonian form of multiple system atrophy.
Clinical autonomic research : official journal of the Clinical Autonomic Research Society.
2015 Feb; 25(1):61-7. doi:
10.1007/s10286-015-0268-z. [PMID: 25638582] - Tatsuya Yamamoto, Tomoyuki Uchiyama, Yoshinori Higuchi, Masato Asahina, Shigeki Hirano, Yoshitaka Yamanaka, Satoshi Kuwabara. Subthalamic Nucleus Deep Brain Stimulation Modulate Catecholamine Levels with Significant Relations to Clinical Outcome after Surgery in Patients with Parkinson's Disease.
PloS one.
2015; 10(9):e0138462. doi:
10.1371/journal.pone.0138462. [PMID: 26394059] - A R Kim, M V Ugryumov. Changes in plasma catecholamines levels as preclinical biomarkers in experimental models of Parkinson's disease.
Doklady. Biochemistry and biophysics.
2015; 464(?):308-11. doi:
10.1134/s1607672915050105. [PMID: 26518555] - Yueting Shao, Hing Man Chan. Effects of methylmercury on dopamine release in MN9D neuronal cells.
Toxicology mechanisms and methods.
2015; 25(8):637-44. doi:
10.3109/15376516.2015.1053654. [PMID: 26056851] - 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] - S Sommer, W Danysz, H Russ, B Valastro, G Flik, W Hauber. The dopamine reuptake inhibitor MRZ-9547 increases progressive ratio responding in rats.
The international journal of neuropsychopharmacology.
2014 Dec; 17(12):2045-56. doi:
10.1017/s1461145714000996. [PMID: 24964269] - Zhaoguang Lu, Junsong Wang, Minghui Li, Qingwang Liu, Dandan Wei, Minghua Yang, Lingyi Kong. (1)H NMR-based metabolomics study on a goldfish model of Parkinson's disease induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP).
Chemico-biological interactions.
2014 Nov; 223(?):18-26. doi:
10.1016/j.cbi.2014.09.006. [PMID: 25242684] - Miklós Sárvári, Levente Deli, Pál Kocsis, László Márk, Gábor Maász, Erik Hrabovszky, Imre Kalló, Dávid Gajári, Csaba Vastagh, Balázs Sümegi, Károly Tihanyi, Zsolt Liposits. Estradiol and isotype-selective estrogen receptor agonists modulate the mesocortical dopaminergic system in gonadectomized female rats.
Brain research.
2014 Oct; 1583(?):1-11. doi:
10.1016/j.brainres.2014.06.020. [PMID: 24976584] - Mari S Golub, Casey E Hogrefe. Fluoxetine: juvenile pharmacokinetics in a nonhuman primate model.
Psychopharmacology.
2014 Oct; 231(20):4041-7. doi:
10.1007/s00213-014-3537-y. [PMID: 24700388] - Farhat Bano, Afrinah Ahmed, Tahira Parveen, Saida Haider. Anxiolytic and hyperlocomotive effects of aqueous extract of Nigella sativa L. seeds in rats.
Pakistan journal of pharmaceutical sciences.
2014 Sep; 27(5 Spec no):1547-52. doi:
". [PMID: 25176249] - Liping Huang, Minzhen Deng, Sheng Zhang, Yongqi Fang, Ling Li. Coadministration of β-asarone and levodopa increases dopamine in rat brain by accelerating transformation of levodopa: a different mechanism from Madopar.
Clinical and experimental pharmacology & physiology.
2014 Sep; 41(9):685-90. doi:
10.1111/1440-1681.12270. [PMID: 24910244] - Man-Jeong Paik, Dong-Kyu Kim, Duc-Toan Nguyen, Gwang Lee, Chae Seo Rhee, In Young Yoon, Jeong-Whun Kim. Correlation of daytime sleepiness with urine metabolites in patients with obstructive sleep apnea.
Sleep & breathing = Schlaf & Atmung.
2014 Sep; 18(3):517-23. doi:
10.1007/s11325-013-0913-5. [PMID: 24402350] - 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] - Katherine M Rose, Mayur S Parmar, Jane E Cavanaugh. Dietary supplementation with resveratrol protects against striatal dopaminergic deficits produced by in utero LPS exposure.
Brain research.
2014 Jul; 1573(?):37-43. doi:
10.1016/j.brainres.2014.05.028. [PMID: 24863468] - Q Yu, C M Teixeira, D Mahadevia, Y Huang, D Balsam, J J Mann, J A Gingrich, M S Ansorge. Dopamine and serotonin signaling during two sensitive developmental periods differentially impact adult aggressive and affective behaviors in mice.
Molecular psychiatry.
2014 Jun; 19(6):688-98. doi:
10.1038/mp.2014.10. [PMID: 24589889] - Yanshu Li, Yan Sun, Junwei Yang, Yanping Wu, Jia Yu, Baixiang Li. Age-dependent dopaminergic dysfunction following fetal exposure to atrazine in SD rats.
Environmental toxicology and pharmacology.
2014 May; 37(3):1275-82. doi:
10.1016/j.etap.2014.04.023. [PMID: 24863964] - S Graziani, D Christin, S Daulon, P Breton, N Perrier, L Taysse. Effects of repeated low-dose exposure of the nerve agent VX on monoamine levels in different brain structures in mice.
Neurochemical research.
2014 May; 39(5):911-21. doi:
10.1007/s11064-014-1286-2. [PMID: 24676701] - Josiane W Bortolotto, Giana P Cognato, Raissa R Christoff, Laura N Roesler, Carlos E Leite, Luiza W Kist, Mauricio R Bogo, Monica R Vianna, Carla D Bonan. Long-term exposure to paraquat alters behavioral parameters and dopamine levels in adult zebrafish (Danio rerio).
Zebrafish.
2014 Apr; 11(2):142-53. doi:
10.1089/zeb.2013.0923. [PMID: 24568596] - Gasem M Abu-Taweel, Zyadah M A, Jamaan S Ajarem, Mohammad Ahmad. Cognitive and biochemical effects of monosodium glutamate and aspartame, administered individually and in combination in male albino mice.
Neurotoxicology and teratology.
2014 Mar; 42(?):60-7. doi:
10.1016/j.ntt.2014.02.001. [PMID: 24556450] - Guoshuai Feng, Zhijian Zhang, Qingqing Bao, Zaijun Zhang, Libing Zhou, Jie Jiang, Sha Li. Protective effect of chinonin in MPTP-induced C57BL/6 mouse model of Parkinson's disease.
Biological & pharmaceutical bulletin.
2014; 37(8):1301-7. doi:
10.1248/bpb.b14-00128. [PMID: 24871044] - Jesselea Carlin, Tiffany E Hill-Smith, Irwin Lucki, Teresa M Reyes. Reversal of dopamine system dysfunction in response to high-fat diet.
Obesity (Silver Spring, Md.).
2013 Dec; 21(12):2513-21. doi:
10.1002/oby.20374. [PMID: 23512420] - Melissa M Kaczmarczyk, Agnieszka S Machaj, Gabriel S Chiu, Marcus A Lawson, Stephen J Gainey, Jason M York, Daryl D Meling, Stephen A Martin, Kristin A Kwakwa, Andrew F Newman, Jeffrey A Woods, Keith W Kelley, Yanyan Wang, Michael J Miller, Gregory G Freund. Methylphenidate prevents high-fat diet (HFD)-induced learning/memory impairment in juvenile mice.
Psychoneuroendocrinology.
2013 Sep; 38(9):1553-64. doi:
10.1016/j.psyneuen.2013.01.004. [PMID: 23411461] - Yuejun Huang, Sihong Chen, Hongwu Xu, Xiaochan Yu, Huihong Lai, Guyu Ho, Qingjun Huang, Xuechuan Shi. Pre-gestational stress alters stress-response of pubertal offspring rat in sexually dimorphic and hemispherically asymmetric manner.
BMC neuroscience.
2013 Jul; 14(?):67. doi:
10.1186/1471-2202-14-67. [PMID: 23829597] - Carl Björkholm, Kent Jardemark, Monica M Marcus, Anna Malmerfelt, Svante Nyberg, Björn Schilström, Torgny H Svensson. Role of concomitant inhibition of the norepinephrine transporter for the antipsychotic effect of quetiapine.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology.
2013 Jul; 23(7):709-20. doi:
10.1016/j.euroneuro.2012.05.012. [PMID: 22732518] - Meizhu Zheng, Yajun Fan, Dongfang Shi, Chunming Liu. Antidepressant-like effect of flavonoids extracted from Apocynum venetum leaves on brain monoamine levels and dopaminergic system.
Journal of ethnopharmacology.
2013 May; 147(1):108-13. doi:
10.1016/j.jep.2013.02.015. [PMID: 23453939] - Susanne M Henning, Piwen Wang, Narine Abgaryan, Roberto Vicinanza, Daniela Moura de Oliveira, Yanjun Zhang, Ru-Po Lee, Catherine L Carpenter, William J Aronson, David Heber. Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer.
Molecular nutrition & food research.
2013 Mar; 57(3):483-93. doi:
10.1002/mnfr.201200646. [PMID: 23319439] - Joshua M Bradner, Tiffany A Suragh, W Wyatt Wilson, Carlos R Lazo, Kristen A Stout, Hye Mi Kim, Min Z Wang, Douglas I Walker, Kurt D Pennell, Jason R Richardson, Gary W Miller, W Michael Caudle. Exposure to the polybrominated diphenyl ether mixture DE-71 damages the nigrostriatal dopamine system: role of dopamine handling in neurotoxicity.
Experimental neurology.
2013 Mar; 241(?):138-47. doi:
10.1016/j.expneurol.2012.12.013. [PMID: 23287494]
