N-Acetyldopamine (BioDeep_00000017806)

 

Secondary id: BioDeep_00000624686, BioDeep_00000869607

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


N-(2-(3,4-Dihydroxyphenyl)ethyl)acetamide (acd/name 4.0)

化学式: C10H13NO3 (195.0895388)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.59%

分子结构信息

SMILES: CC(=O)NCCC1=CC(=C(C=C1)O)O
InChI: InChI=1S/C10H13NO3/c1-7(12)11-5-4-8-2-3-9(13)10(14)6-8/h2-3,6,13-14H,4-5H2,1H3,(H,11,12)

描述信息

N-Acetyldopamine also known as NADA is an acetylated form of dopamine. It is an endogenously produced derivative or metabolite of dopamine. It belongs to the family of compounds known as catecholamines and derivatives. These are compounds containing 4-(2-aminoethyl) pyrocatechol [4-(2-aminoethyl) benzene-1,2-diol] or a derivative thereof. While NADA has been found in the human liver, kidney, and urine, it is unclear what its role is in mammal physiology (PMID: 16179545). NADA exists in both free and conjugated (glucuronide) forms. Conjugated NADA accounts for about 90\\\% of the total excretion of NADA. Urinary excretion of total N-acetyldopamine averages 0.485 micromoles/day in healthy humans (PMID: 6513727). The concentration of NADA is thirteen times higher in children with neuroblastoma than in normal subjects (PMID: 1321164). NADA is known to be a sepiapterin reductase inhibitor (PMID: 16179545). N-acetyldopamine has been shown to inhibit lipopolysaccharide-induced lipid peroxidation in rat brains (PMID: 16179545).
N-acetyldopamine (NADA) is a catecholamine that is used by insects as sclerotizing precursors to harden their cuticle[1].

同义名列表

9 个代谢物同义名

N-(2-(3,4-Dihydroxyphenyl)ethyl)acetamide (acd/name 4.0); N-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid; {N-[2-(3,} 4-dihydroxyphenyl)ethyl]-acetamide; N-(3,4-Dihydroxyphenethyl)-acetamide; N-Acetyldopamine hydrobromide; N-Acetyl-dopamine; N-Acetyldopamine; NSC 314644; NADA



数据库引用编号

13 个数据库交叉引用编号

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)

7 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。



文献列表

  • Jiaozhen Zhang, Fangfang Dong, Yongjie Wang, Chan Wang, Chengmin Zhang, Ke Xu, Tao Shen, Hongxiang Lou. N-acetyldopamine oligomers from Periplaneta americana with anti-inflammatory and vasorelaxant effects and their spatial distribution visualized by mass spectrometry imaging. Journal of ethnopharmacology. 2024 Jan; 318(Pt B):116989. doi: 10.1016/j.jep.2023.116989. [PMID: 37532069]
  • Meng-Fei Guo, Jing Zhou, Huan-Huan Zhang, Ping Zhong, Jin-Di Xu, Shan-Shan Zhou, Fang Long, He Zhu, Qian Mao, Song-Lin Li. UPLC-QTOF-MS/MS assisted UPLC-TQ-MS/MS strategy to comparatively investigate the rat pharmacokinetics of N-acetyldopamine oligomers derived from Cicadae Periostracum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2023 Jul; 1226(?):123806. doi: 10.1016/j.jchromb.2023.123806. [PMID: 37348161]
  • Fengge Yang, Sihao Zhang, Danmei Tian, Guirong Zhou, Xiyang Tang, Xinglong Miao, Yi He, Xinsheng Yao, Jinshan Tang. Deciphering chemical and metabolite profiling of Chang-Kang-Fang by UPLC-Q-TOF-MS/MS and its potential active components identification. Chinese journal of natural medicines. 2023 Jun; 21(6):459-480. doi: 10.1016/s1875-5364(23)60474-1. [PMID: 37407177]
  • Meng-Fei Guo, Huan-Huan Zhang, Ping Zhong, Jin-Di Xu, Shan-Shan Zhou, Fang Long, Ming Kong, Qian Mao, Song-Lin Li. Integrating Multi-Type Component Determination and Anti-Oxidant/-Inflammatory Assay to Evaluate the Impact of Pre-Molting Washing on the Quality and Bioactivity of Cicadae Periostracum. Molecules (Basel, Switzerland). 2022 Nov; 27(22):. doi: 10.3390/molecules27227683. [PMID: 36431784]
  • Lijun Huang, Leiqiang Gong, Xueyan Huo, Lirong Lei, Qi Zhang, Yunjie Hu, Qixuan Kuang, Yu Gui, Yifei Dai, Yucheng Gu, Yun Deng, Dong Wang, Dale Guo. N-acetyldopamine dimer inhibits neuroinflammation through the TLR4/NF-κB and NLRP3/Caspase-1 pathways. Acta biochimica et biophysica Sinica. 2022 Aug; 55(1):23-33. doi: 10.3724/abbs.2022116. [PMID: 36017888]
  • Xin-Ci Cao, Meng-Fei Guo, Ying Han, Yan-Ting Fan, Jin-Hao Zhu, He Zhu, Jin-Di Xu, Hong Shen, Gui-Rong Zhou, Qian Mao, Song-Lin Li. Systematic metabolite profiling of N-acetyldopamine oligomers from Cicadae Periostracum in rats by ultra-high performance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2021 Jan; 192(?):113665. doi: 10.1016/j.jpba.2020.113665. [PMID: 33120311]
  • Wei-Yi Ding, Yong-Ming Yan, Xiao-Hui Meng, Laurence A Nafie, Te Xu, Rina K Dukor, Hong-Bo Qin, Yong-Xian Cheng. Isolation, Total Synthesis, and Absolute Configuration Determination of Renoprotective Dimeric N-Acetyldopamine-Adenine Hybrids from the Insect Aspongopus chinensis. Organic letters. 2020 08; 22(15):5726-5730. doi: 10.1021/acs.orglett.0c01593. [PMID: 32525688]
  • Xin-Ci Cao, Xiao-Ya Zhang, Jin-Di Xu, Hong Shen, Shan-Shan Zhou, He Zhu, Ming Kong, Wei Zhang, Gui-Rong Zhou, Yi He, Qian Mao, Song-Lin Li. Quality consistency evaluation on four origins of Cicadae Periostracum by ultra-performance liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry analysis. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 179(?):112974. doi: 10.1016/j.jpba.2019.112974. [PMID: 31767224]
  • Yong-Ming Yan, Qin Luo, Lei Di, Yan-Ni Shi, Zheng-Chao Tu, Yong-Xian Cheng. Nucleoside and N-acetyldopamine derivatives from the insect Aspongopus chinensis. Fitoterapia. 2019 Jan; 132(?):82-87. doi: 10.1016/j.fitote.2018.12.005. [PMID: 30521857]
  • Juan Lu, Qin Sun, Zheng-Chao Tu, Qing Lv, Pi-Xian Shui, Yong-Xian Cheng. Identification of N-Acetyldopamine Dimers from the Dung Beetle Catharsius molossus and Their COX-1 and COX-2 Inhibitory Activities. Molecules (Basel, Switzerland). 2015 Aug; 20(9):15589-96. doi: 10.3390/molecules200915589. [PMID: 26343619]
  • Yan-Ni Shi, Zheng-Chao Tu, Xin-Long Wang, Yong-Ming Yan, Ping Fang, Zhi-Li Zuo, Bo Hou, Tong-Hua Yang, Yong-Xian Cheng. Bioactive compounds from the insect Aspongopus chinensis. Bioorganic & medicinal chemistry letters. 2014 Nov; 24(22):5164-9. doi: 10.1016/j.bmcl.2014.09.083. [PMID: 25442305]
  • Yong-Ming Yan, Jun Ai, Yan-Ni Shi, Zhi-Li Zuo, Bo Hou, Jie Luo, Yong-Xian Cheng. (±)-Aspongamide A, an N-acetyldopamine trimer isolated from the insect Aspongopus chinensis, is an inhibitor of p-Smad3. Organic letters. 2014 Jan; 16(2):532-5. doi: 10.1021/ol403409v. [PMID: 24383883]
  • Hai-Long Jiang, Xiao-Hong Luo, Xiao-Zheng Wang, Jun-Li Yang, Xiao-Jun Yao, Phillip Crews, Frederick A Valeriote, Quan-Xiang Wu. New isocoumarins and alkaloid from Chinese insect medicine, Eupolyphaga sinensis Walker. Fitoterapia. 2012 Oct; 83(7):1275-80. doi: 10.1016/j.fitote.2012.06.005. [PMID: 22735600]
  • Congjing Feng, Qisheng Song, Wenjing Lü, Jianfeng Lu. Purification and characterization of hemolymph prophenoloxidase from Ostrinia furnacalis (Lepidoptera: Pyralidae) larvae. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2008 Oct; 151(2):139-46. doi: 10.1016/j.cbpb.2008.05.012. [PMID: 18577463]
  • Shiheng An, Songjie Wang, Lawrence I Gilbert, Brenda Beerntsen, Mark Ellersieck, Qisheng Song. Global identification of bursicon-regulated genes in Drosophila melanogaster. BMC genomics. 2008 Sep; 9(?):424. doi: 10.1186/1471-2164-9-424. [PMID: 18801173]
  • Mary C Perianayagam, Pura J Requintina, Bertrand L Jaber, Gregory F Oxenkrug. Effect of methyl derivatives of dopamine on tumor necrosis factor alpha and lipid peroxidation. Annals of the New York Academy of Sciences. 2007 Dec; 1122(?):253-9. doi: 10.1196/annals.1403.018. [PMID: 18077578]
  • Picheng Zhao, Jiajing Li, Yang Wang, Haobo Jiang. Broad-spectrum antimicrobial activity of the reactive compounds generated in vitro by Manduca sexta phenoloxidase. Insect biochemistry and molecular biology. 2007 Sep; 37(9):952-9. doi: 10.1016/j.ibmb.2007.05.001. [PMID: 17681234]
  • Ming-Zhe Xu, Woo Song Lee, Jong-Min Han, Hyun-Woo Oh, Doo-Sang Park, Guan-Rong Tian, Tae-Sook Jeong, Ho-Yong Park. Antioxidant and anti-inflammatory activities of N-acetyldopamine dimers from Periostracum Cicadae. Bioorganic & medicinal chemistry. 2006 Dec; 14(23):7826-34. doi: 10.1016/j.bmc.2006.07.063. [PMID: 16919462]
  • Gregory F Oxenkrug, Pura J Requintina. N-acetyldopamine inhibits rat brain lipid peroxidation induced by lipopolysaccharide. Annals of the New York Academy of Sciences. 2005 Aug; 1053(?):394-9. doi: 10.1111/j.1749-6632.2005.tb00047.x. [PMID: 16179545]
  • Kian Hong Ng, Beng Gek Lim, Kim Ping Wong. Sulfate conjugating and transport functions of MDCK distal tubular cells. Kidney international. 2003 Mar; 63(3):976-86. doi: 10.1046/j.1523-1755.2003.00818.x. [PMID: 12631078]
  • N Noda, S Kubota, Y Miyata, K Miyahara. Optically active N-acetyldopamine dimer of the crude drug 'Zentai,' the cast-off shell of the Cicada, Cryptotympana sp. Chemical & pharmaceutical bulletin. 2000 Nov; 48(11):1749-52. doi: 10.1248/cpb.48.1749. [PMID: 11086906]
  • V Kahn, N Ben-Shalom. Effect of maltol on the oxidation of DL-DOPA, dopamine, N-acetyldopamine (NADA), and norepinephrine by mushroom tyrosinase. Pigment cell research. 1997 Jun; 10(3):139-49. doi: 10.1111/j.1600-0749.1997.tb00475.x. [PMID: 9266600]
  • F A Muskiet, I P Kema. Sensitivity and specificity of urinary N-acetyldopamine as a marker for neuroblastomas: comparison with traditional urinary catecholamine metabolites. Journal of chromatography. 1992 Aug; 579(1):184-6; discussion 187. doi: 10.1016/0378-4347(92)80378-4. [PMID: 1447347]
  • J Jouve, J Herault, H Tournade, J P Muh. Determination by high-performance liquid chromatography with electrochemical detection of free and conjugated N-acetyldopamine excretion in urine of children with neuroblastoma and nephroblastoma. Journal of chromatography. 1992 Feb; 574(1):9-15. doi: 10.1016/0378-4347(92)80092-5. [PMID: 1321164]
  • M A Elchisak, E A Hausner. Demonstration of N-acetyldopamine in human kidney and urine. Life sciences. 1984 Dec; 35(25):2561-9. doi: 10.1016/0024-3205(84)90444-2. [PMID: 6513727]
  • A HANSON, VON STUDNITZ. DEMONSTRATION OF URINARY N-ACETYLDOPAMINE IN PATIENTS WITH NEUROBLASTOMA. Clinica chimica acta; international journal of clinical chemistry. 1965 Apr; 11(?):384-5. doi: 10.1016/0009-8981(65)90231-7. [PMID: 14323686]