Citraconic acid (BioDeep_00000014361)

 

Secondary id: BioDeep_00000400098, BioDeep_00000629394

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


(2Z)-2-methylbut-2-enedioic acid

化学式: C5H6O4 (130.0266)
中文名称: 柠檬酸, 柠康酸
谱图信息: 最多检出来源 Homo sapiens(feces) 17.41%

Reviewed

Last reviewed on 2024-07-15.

Cite this Page

Citraconic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/citraconic_acid (retrieved 2024-12-23) (BioDeep RN: BioDeep_00000014361). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C/C(=C/C(=O)O)/C(=O)O
InChI: InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

描述信息

Citraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid is a dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position. Citraconic acid exists as a white solid. It is the cis-isomer of mesaconic acid and is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid has been detected in the urine of both normal and fasting individuals (PMID: 6778884). Citraconic acid is also elevated in the urine of individuals with methylmalonic acidaemia who have suffered ketotic attacks (PMID: 116077). Altered serum levels of citraconic acid have been detected in patients with primary biliary cholangitis (PMID: 28400566).
Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction. [HMDB]

Citraconic acid belongs to the class of organic compounds known as methyl-branched fatty acids.

同义名列表

36 个代谢物同义名

(2Z)-2-methylbut-2-enedioic acid; (e)-2-Methyl-2-butenedioic acid; 2-methyl-2-but-2Z-enedioic acid; (Z)-2-Methyl-2-butenedioic acid; Citraconic acid, ammonium salt; Citraconic acid, calcium salt; cis-2-Methylbutenedioic acid; Citraconic acid, sodium salt; Citraconic acid, (e)-isomer; (Z)-2-Methyl-2-butenedioate; 2-Methyl-2-butenedioic acid; cis-Methylbutenedioic acid; cis-2-Methylbutenedioate; alpha-Methylmaleic acid; 2-Methyl-2-butenedioate; cis-Methylbutenedioate; 2-Methylmaleic acid; a-Methylmaleic acid; alpha-Methylmaleate; Α-methylmaleic acid; Methyl-maleinsaeure; Monomethylfumarate; Methylfumaric acid; Methylmaleic acid; Citraconic acid; 2-Methylmeleate; 2-Methylmaleate; a-Methylmaleate; Α-methylmaleate; Mesaconic acid; Citraconsaeure; Methylmaleate; Citraconate; Citraconic acid; Citraconic acid; 2-Methylmaleate



数据库引用编号

33 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

1 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(1)

PharmGKB(0)

2 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


文献列表

  • Randa Sghaier, Thomas Nury, Valerio Leoni, Claudio Caccia, Jean-Paul Pais De Barros, Ameur Cherif, Anne Vejux, Thibault Moreau, Khalifa Limem, Mohammad Samadi, John J Mackrill, Ahmed Slaheddine Masmoudi, Gérard Lizard, Amira Zarrouk. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrial alterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. The Journal of steroid biochemistry and molecular biology. 2019 11; 194(?):105432. doi: 10.1016/j.jsbmb.2019.105432. [PMID: 31344443]
  • Irene De Biase, Marzia Pasquali, Alexander Asamoah. Unusual Metabolites in a Patient with Isovaleric Acidemia. Clinical chemistry. 2019 04; 65(4):595-597. doi: 10.1373/clinchem.2018.300558. [PMID: 30923063]
  • Armin Azadkhah Shalmani, Mohammad Hossein Ghahremani, Fereshteh Jeivad, Amir Shadboorestan, Gholamreza Hassanzadeh, Abbas Beh-Pajooh, Mikhriy Ganbari-Erdi, Sara Kasirzadeh, Mojtaba Mojtahedzadeh, Omid Sabzevari. Monomethyl fumarate alleviates sepsis-induced hepatic dysfunction by regulating TLR-4/NF-κB signalling pathway. Life sciences. 2018 Dec; 215(?):152-158. doi: 10.1016/j.lfs.2018.11.010. [PMID: 30412724]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Ulrich Mrowietz, Peter John Morrison, Ina Suhrkamp, Margaret Kumanova, Bernd Clement. The Pharmacokinetics of Fumaric Acid Esters Reveal Their In Vivo Effects. Trends in pharmacological sciences. 2018 01; 39(1):1-12. doi: 10.1016/j.tips.2017.11.002. [PMID: 29183628]
  • Bing Zhu, Ivan Nestorov, Guolin Zhao, Venkata Meka, Mark Leahy, Jeanelle Kam, Sarah I Sheikh. Evaluation of Potential Drug-Drug Interaction Between Delayed-Release Dimethyl Fumarate and a Commonly Used Oral Contraceptive (Norgestimate/Ethinyl Estradiol) in Healthy Women. Clinical pharmacology in drug development. 2017 Nov; 6(6):604-613. doi: 10.1002/cpdd.377. [PMID: 28783872]
  • Michael John Kerins, Ajay Amar Vashisht, Benjamin Xi-Tong Liang, Spencer Jordan Duckworth, Brandon John Praslicka, James Akira Wohlschlegel, Aikseng Ooi. Fumarate Mediates a Chronic Proliferative Signal in Fumarate Hydratase-Inactivated Cancer Cells by Increasing Transcription and Translation of Ferritin Genes. Molecular and cellular biology. 2017 06; 37(11):. doi: 10.1128/mcb.00079-17. [PMID: 28289076]
  • Anshul Shakya, Upendra Kumar Soni, Geeta Rai, Shyam Sunder Chatterjee, Vikas Kumar. Gastro-protective and Anti-stress Efficacies of Monomethyl Fumarate and a Fumaria indica Extract in Chronically Stressed Rats. Cellular and molecular neurobiology. 2016 May; 36(4):621-35. doi: 10.1007/s10571-015-0243-1. [PMID: 26215054]
  • C C Tangney, N T Aggarwal, H Li, R S Wilson, C Decarli, D A Evans, M C Morris. Vitamin B12, cognition, and brain MRI measures: a cross-sectional examination. Neurology. 2011 Sep; 77(13):1276-82. doi: 10.1212/wnl.0b013e3182315a33. [PMID: 21947532]
  • Qin Yi, Juanjuan Lv, Fengyan Tian, Hong Wei, Qin Ning, Xiaoping Luo. Clinical characteristics and gene mutation analysis of methylmalonic aciduria. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban. 2011 Jun; 31(3):384-389. doi: 10.1007/s11596-011-0386-3. [PMID: 21671183]
  • Martin Rostami-Yazdi, Bernd Clement, Ulrich Mrowietz. Pharmacokinetics of anti-psoriatic fumaric acid esters in psoriasis patients. Archives of dermatological research. 2010 Sep; 302(7):531-8. doi: 10.1007/s00403-010-1061-4. [PMID: 20574745]
  • Turgay Celik, Ejder Kardesoglu, Atila Iyisoy, Omer Ozcan, Selim Kilic, Halil Yaman. Urinary methylmalonic acid in patients with acute myocardial infarction. Medical principles and practice : international journal of the Kuwait University, Health Science Centre. 2009; 18(3):217-22. doi: 10.1159/000204353. [PMID: 19349725]
  • Hua Tang, Jenny Ying-Lin Lu, Xiaomu Zheng, Yuhua Yang, Jeff D Reagan. The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. Biochemical and biophysical research communications. 2008 Oct; 375(4):562-5. doi: 10.1016/j.bbrc.2008.08.041. [PMID: 18722346]
  • I Pela, S Gasperini, E Pasquini, M A Donati. Hyperkalemia after acute metabolic decompensation in two children with vitamin B12-unresponsive methylmalonic acidemia and normal renal function. Clinical nephrology. 2006 Jul; 66(1):63-6. doi: 10.5414/cnp66063. [PMID: 16878438]
  • Nicolle H R Litjens, Elisabeth van Strijen, Co van Gulpen, Herman Mattie, Jaap T van Dissel, H Bing Thio, Peter H Nibbering. In vitro pharmacokinetics of anti-psoriatic fumaric acid esters. BMC pharmacology. 2004 Oct; 4(?):22. doi: 10.1186/1471-2210-4-22. [PMID: 15479475]
  • O Befani, M T Graziani, E Agostinelli, E Grippa, B Mondovì, M A Mateescu. Serum amine oxidase can specifically recognize and oxidize aminohexyl (AH) chains on AH-Sepharose support: single-step affinity immobilization. Biotechnology and applied biochemistry. 1998 Oct; 28 ( Pt 2)(?):99-104. doi: NULL. [PMID: 9756636]
  • K S Rao, S H Mishra. Antihepatotoxic activity of monomethyl fumarate isolated from Fumaria indica. Journal of ethnopharmacology. 1998 Apr; 60(3):207-13. doi: 10.1016/s0378-8741(97)00149-9. [PMID: 9613834]
  • P H Nibbering, B Thio, A C Bezemer, R L Beijersbergen, T P Zomerdijk. Intracellular signalling by binding sites for the antipsoriatic agent monomethylfumarate on human granulocytes. The British journal of dermatology. 1997 Jul; 137(1):65-75. doi: NULL. [PMID: 9274627]