Mesaconic acid (BioDeep_00000001310)

 

Secondary id: BioDeep_00000270832, BioDeep_00000865569

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


trans-1-Propene-1,2-dicarboxylic acid

化学式: C5H6O4 (130.0266)
中文名称: 中康酸
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 27.18%

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

Mesaconic acid, also known as 2-methylfumarate or citronic 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. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van\\%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.
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]
Acquisition and generation of the data is financially supported in part by CREST/JST.
D003879 - Dermatologic Agents

同义名列表

30 个代谢物同义名

trans-1-Propene-1,2-dicarboxylic acid; trans-2-Methyl-2-butenedioic acid; trans-1-Propene-1,2-dicarboxylate; (2E)-2-methylbut-2-enedioic acid; (2E)-2-Methyl-2-butenedioic acid; (e)-2-Methyl-2-butenedioic acid; (Z)-2-Methyl-2-butenedioic acid; Citraconic acid, ammonium salt; trans-2-Methyl-2-butenedioate; 2-methyl-but-2E-enedioic acid; Citraconic acid, calcium salt; (2E)-2-Methyl-2-butenedioate; Citraconic acid, sodium salt; (e)-2-Methyl-2-butenedioate; Citraconic acid, (e)-isomer; 2-Methylfumaric acid; (e)-Citraconic acid; Monomethylfumarate; Methylfumaric acid; Methylmaleic acid; 2-Methylfumarate; Citraconic acid; (e)-Citraconate; Mesaconic acid; Methylfumarate; Citronic acid; Mesaconate; Citronate; Mesaconate; Mesaconic acid



数据库引用编号

24 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)

21 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 9 DBH, FH, GAPDH, JAK1, KEAP1, NLRP3, PAM, PFDN5, TFEB
Peripheral membrane protein 1 ACHE
Nucleus 13 ACHE, ATF3, CS, FH, GABPA, GAPDH, JAK1, KEAP1, NLRP3, PAM, PFDN5, TET2, TFEB
cytosol 8 FH, GAPDH, JAK1, KEAP1, NLRP3, PAM, PFDN5, TFEB
nucleoplasm 5 ATF3, GABPA, KEAP1, PAM, TET2
RNA polymerase II transcription regulator complex 1 ATF3
Cell membrane 1 ACHE
Cell projection, axon 1 PAM
Multi-pass membrane protein 1 SLC9C1
Golgi apparatus membrane 1 NLRP3
Synapse 2 ACHE, DBH
cell surface 1 ACHE
Golgi apparatus 1 ACHE
Golgi membrane 1 NLRP3
lysosomal membrane 1 TFEB
mitochondrial inner membrane 1 L2HGDH
neuromuscular junction 1 ACHE
Cytoplasm, cytosol 3 GAPDH, NLRP3, TFEB
endosome 1 JAK1
plasma membrane 6 ACHE, GAPDH, IFNLR1, JAK1, PAM, SLC9C1
Membrane 10 ACHE, CS, DBH, GAPDH, IFNLR1, JAK1, L2HGDH, NLRP3, PAM, SLC9C1
axon 1 PAM
extracellular exosome 4 CS, FH, GAPDH, PAM
Lysosome membrane 1 TFEB
endoplasmic reticulum 3 DBH, KEAP1, NLRP3
extracellular space 3 ACHE, CXCL10, DBH
perinuclear region of cytoplasm 2 ACHE, GAPDH
mitochondrion 5 ACOD1, CS, FH, L2HGDH, NLRP3
intracellular membrane-bounded organelle 3 DBH, GAPDH, PAM
Single-pass type I membrane protein 1 IFNLR1
Secreted 4 ACHE, CXCL10, DBH, NLRP3
extracellular region 5 ACHE, CXCL10, DBH, NLRP3, PAM
cytoplasmic side of plasma membrane 1 JAK1
Single-pass membrane protein 1 PAM
Mitochondrion matrix 1 CS
mitochondrial matrix 2 CS, FH
Extracellular side 1 ACHE
centriolar satellite 2 DBH, KEAP1
motile cilium 1 SLC9C1
nuclear membrane 1 GAPDH
external side of plasma membrane 1 CXCL10
microtubule cytoskeleton 2 GAPDH, PAM
nucleolus 1 ATF3
midbody 1 KEAP1
Single-pass type II membrane protein 1 DBH
vesicle 1 GAPDH
Cytoplasm, perinuclear region 1 GAPDH
Cytoplasm, cytoskeleton 2 GAPDH, PAM
focal adhesion 1 JAK1
basement membrane 1 ACHE
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
chromatin 3 ATF3, GABPA, TFEB
Chromosome 2 FH, TET2
cytoskeleton 2 GAPDH, JAK1
actin filament 1 KEAP1
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 FH
Cul3-RING ubiquitin ligase complex 1 KEAP1
Endomembrane system 2 JAK1, NLRP3
Lipid droplet 1 GAPDH
microtubule organizing center 1 NLRP3
Cell projection, cilium, flagellum membrane 1 SLC9C1
side of membrane 1 ACHE
intermediate filament cytoskeleton 1 PFDN5
secretory granule lumen 1 DBH
secretory granule membrane 2 DBH, PAM
ribonucleoprotein complex 1 GAPDH
extrinsic component of cytoplasmic side of plasma membrane 1 JAK1
prefoldin complex 1 PFDN5
synaptic cleft 1 ACHE
Cytoplasmic vesicle, secretory vesicle membrane 2 DBH, PAM
GAIT complex 1 GAPDH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
transport vesicle membrane 2 DBH, PAM
inclusion body 1 KEAP1
[Isoform Mitochondrial]: Mitochondrion 1 FH
[Isoform Cytoplasmic]: Cytoplasm, cytosol 1 FH
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
CHOP-ATF3 complex 1 ATF3
[Isoform H]: Cell membrane 1 ACHE
interleukin-28 receptor complex 1 IFNLR1


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]
  • 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]
  • 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]