Methylmalonic acid (BioDeep_00000001672)

 

Secondary id: BioDeep_00000265247, BioDeep_00000413320, BioDeep_00000629090

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


1,1-Ethanedicarboxylic acid

化学式: C4H6O4 (118.0266)
中文名称: 甲基丙二酸
谱图信息: 最多检出来源 Homo sapiens(plant) 16.71%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Methylmalonic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/methylmalonic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001672). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(C(=O)O)C(=O)O
InChI: InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)

描述信息

Methylmalonic acid is a malonic acid derivative, which is a vital intermediate in the metabolism of fat and protein. In particular, the coenzyme A-linked form of methylmalonic acid, methylmalonyl-CoA, is converted into succinyl-CoA by methylmalonyl-CoA mutase in a reaction that requires vitamin B12 as a cofactor. In this way, methylmalonic acid enters the Krebs cycle and is thus part of one of the anaplerotic reactions. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This inborn error of metabolism is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. Methylmalonic acid is also found to be associated with other inborn errors of metabolism, including cobalamin deficiency, cobalamin malabsorption, malonyl-CoA decarboxylase deficiency, and transcobalamin II deficiency. When present in sufficiently high levels, methylmalonic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methylmalonic acid are associated with at least 5 inborn errors of metabolism, including Malonyl CoA decarboxylase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria and Methylmalonic Aciduria Due to Cobalamin-Related Disorders. Methylmalonic acid is an organic acid and abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. [HMDB]
KEIO_ID M014
Methylmalonic acid (Methylmalonate) is an indicator of Vitamin B-12 deficiency in cancer.
Methylmalonic acid (Methylmalonate) is an indicator of Vitamin B-12 deficiency in cancer.

同义名列表

26 个代谢物同义名

1,1-Ethanedicarboxylic acid; 2-methyl-propanedioic acid; 2-methylpropanedioic acid; alpha-Methylmalonic acid; Methyl-propanedioic acid; 1,1-Ethanedicarboxylate; Methylpropanedioic acid; Α-methylmalonic acid; a-Methylmalonic acid; Methyl-propanedioate; 2-Methylmalonic acid; alpha-Methylmalonate; Methyl-malonic acid; Acid, methylmalonic; Methylpropanedioate; Methylmalonic acid; a-Methylmalonate; Isosuccinic acid; 2-Methylmalonate; Α-methylmalonate; Methyl-malonate; Methylmalonate; Isosuccinate; Methylmalonic acid; Methylmalonate; Methylmalonic acid



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

68 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(67)

PharmGKB(0)

28 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 8 ALB, AXIN2, CBLB, CBS, MMAA, MMUT, MTR, SUCLA2
Nucleus 3 ALB, AXIN2, CBS
cytosol 10 ALB, ATP12A, AXIN2, CBL, CBLB, CBS, MMAA, MTHFR, MTR, MTRR
centrosome 2 ALB, AXIN2
nucleoplasm 4 ACSF3, ATP2B1, CBLB, MTRR
Cell membrane 1 ATP2B1
Multi-pass membrane protein 3 ATP12A, ATP2B1, MMAA
Synapse 1 ATP2B1
glutamatergic synapse 2 ATP2B1, CBLB
Golgi apparatus 2 ALB, CBL
growth cone 1 CBL
postsynapse 1 CBLB
presynaptic membrane 1 ATP2B1
plasma membrane 7 ATP12A, ATP2B1, AXIN2, CBL, CBLB, CBLC, TCN2
synaptic vesicle membrane 1 ATP2B1
Membrane 2 ATP2B1, MMAA
apical plasma membrane 1 ATP12A
basolateral plasma membrane 2 ATP12A, ATP2B1
extracellular exosome 3 ALB, ATP2B1, SUCLA2
endoplasmic reticulum 1 ALB
extracellular space 5 ALB, CRP, GAST, TCN1, TCN2
lysosomal lumen 1 TCN2
perinuclear region of cytoplasm 1 CBL
mitochondrion 5 ACSF3, MCEE, MMAA, MMUT, SUCLA2
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 1 ATP2B1
Secreted 4 ALB, CRP, GAST, TCN2
extracellular region 5 ALB, CRP, GAST, TCN1, TCN2
Mitochondrion matrix 1 MMUT
mitochondrial matrix 5 ACSF3, MCEE, MMAA, MMUT, SUCLA2
anchoring junction 1 ALB
Cell projection, cilium 1 CBL
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 TCN2
actin cytoskeleton 1 ATP12A
beta-catenin destruction complex 1 AXIN2
Apical cell membrane 1 ATP12A
Membrane raft 3 CBL, CBLB, CBLC
focal adhesion 1 CBL
flotillin complex 1 CBL
lateral plasma membrane 1 ATP2B1
ciliary basal body 1 ALB
cilium 1 CBL
cell projection 1 ATP2B1
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 1 ATP2B1
Presynaptic cell membrane 1 ATP2B1
intermediate filament cytoskeleton 1 MTRR
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
specific granule lumen 1 TCN1
tertiary granule lumen 1 TCN1
immunological synapse 1 ATP2B1
photoreceptor ribbon synapse 1 ATP2B1
potassium:proton exchanging ATPase complex 1 ATP12A
ciliary transition fiber 1 ALB
succinate-CoA ligase complex (ADP-forming) 1 SUCLA2
[Isoform A]: Cytoplasm 1 MTRR
succinate-CoA ligase complex 1 SUCLA2


文献列表

  • Yan Liu, Zemin Huang, Hongbin Qiu, Fan Tang, Fengyi Liu, Yiying Zhang, Shanjie Wang. The association between serum methylmalonic acid, cobalamin-related biomarkers, and long-term mortality risk in cancer survivors: a prospective cohort study. The American journal of clinical nutrition. 2024 May; 119(5):1122-1132. doi: 10.1016/j.ajcnut.2024.02.009. [PMID: 38702109]
  • Tongliang Wang, Yaqi Zeng, Chaoxin Ma, Jun Meng, Jianwen Wang, Wanlu Ren, Chuankun Wang, Xinxin Yuan, Xixi Yang, Xinkui Yao. Plasma Non-targeted Metabolomics Analysis of Yili Horses Raced on Tracks With Different Surface Hardness. Journal of equine veterinary science. 2023 Feb; 121(?):104197. doi: 10.1016/j.jevs.2022.104197. [PMID: 36572130]
  • Pierce Marsden, Aakriti A Sharma, Joe-Anthony Rotella. Review article: Clinical manifestations and outcomes of chronic nitrous oxide misuse: A systematic review. Emergency medicine Australasia : EMA. 2022 08; 34(4):492-503. doi: 10.1111/1742-6723.13997. [PMID: 35695047]
  • Marsha E Samson, Lorraine F Yeung, Charles E Rose, Yan Ping Qi, Christopher A Taylor, Krista S Crider. Vitamin B-12 malabsorption and renal function are critical considerations in studies of folate and vitamin B-12 interactions in cognitive performance: NHANES 2011-2014. The American journal of clinical nutrition. 2022 07; 116(1):74-85. doi: 10.1093/ajcn/nqac065. [PMID: 35584808]
  • Özen Taş, Tugba Kontbay, Ozlem Dogan, Engin Kose, Merih Berberoglu, Zeynep Siklar, Leyla Tumer, Fatma Tuba Eminoglu. Does Metformin Treatment in Pediatric Population Cause Vitamin B12 Deficiency?. Klinische Padiatrie. 2022 Jul; 234(4):221-227. doi: 10.1055/a-1702-2614. [PMID: 35114702]
  • Scott Ailliet, Rik Vandenberghe, Toon Schiemsky, Lode Van Overbeke, Philippe Demaerel, Wouter Meersseman, David Cassiman, Pieter Vermeersch. A case of vitamin B12 deficiency neurological syndrome in a young adult due to late-onset cobalamin C (CblC) deficiency: a diagnostic challenge. Biochemia medica. 2022 Jun; 32(2):020802. doi: 10.11613/bm.2022.020802. [PMID: 35464742]
  • William D Wood, Ayah Elmaghrabi, Garrett Gotway, Matthias T F Wolf. The roles of homocysteinemia and methylmalonic acidemia in kidney injury in atypical hemolytic uremic syndrome caused by cobalamin C deficiency. Pediatric nephrology (Berlin, Germany). 2022 06; 37(6):1415-1418. doi: 10.1007/s00467-021-05372-6. [PMID: 34854955]
  • Michel Boutin, Nancy Presse, David Allard, Tristan Martineau, Pierrette Gaudreau, Christiane Auray-Blais. Methylmalonic acid analysis using urine filter paper samples to screen for metabolic vitamin B12 deficiency in older adults. Bioanalysis. 2022 May; 14(9):615-626. doi: 10.4155/bio-2022-0007. [PMID: 35546317]
  • Jai Kumar, Razium Ali Soomro, Rana R Neiber, Nazeer Ahmed, Shymaa S Medany, Munirah D Albaqami, Ayman Nafady. Ni Nanoparticles Embedded Ti3C2Tx-MXene Nanoarchitectures for Electrochemical Sensing of Methylmalonic Acid. Biosensors. 2022 Apr; 12(4):. doi: 10.3390/bios12040231. [PMID: 35448291]
  • Shanjie Wang, Ye Wang, Xin Wan, Junchen Guo, Yiying Zhang, Maoyi Tian, Shaohong Fang, Bo Yu. Cobalamin Intake and Related Biomarkers: Examining Associations With Mortality Risk Among Adults With Type 2 Diabetes in NHANES. Diabetes care. 2022 02; 45(2):276-284. doi: 10.2337/dc21-1674. [PMID: 34862259]
  • Anders Abildgaard, Cindy Soendersoe Knudsen, Carsten Schriver Hoejskov, Eva Greibe, Tina Parkner. Reference intervals for plasma vitamin B12 and plasma/serum methylmalonic acid in Danish children, adults and elderly. Clinica chimica acta; international journal of clinical chemistry. 2022 Jan; 525(?):62-68. doi: 10.1016/j.cca.2021.12.015. [PMID: 34942168]
  • Yupeng Liu, Zhehui Chen, Lulu Kang, Ruxuan He, Jinqing Song, Yi Liu, Chunyan Shi, Junya Chen, Hui Dong, Yao Zhang, Yanyan Ma, Tongfei Wu, Qiao Wang, Yuan Ding, Xiyuan Li, Dongxiao Li, Mengqiu Li, Ying Jin, Jiong Qin, Yanling Yang. Comparing amniotic fluid mass spectrometry assays and amniocyte gene analyses for the prenatal diagnosis of methylmalonic aciduria. PloS one. 2022; 17(3):e0265766. doi: 10.1371/journal.pone.0265766. [PMID: 35358224]
  • Katarína Brennerová, Martina Škopková, Mária Ostrožlíková, Jana Šaligová, Juraj Staník, Vladimír Bzdúch, Daniela Gašperíková. Genetic testing is necessary for correct diagnosis and treatment in patients with isolated methylmalonic aciduria: a case report. BMC pediatrics. 2021 12; 21(1):578. doi: 10.1186/s12887-021-03067-3. [PMID: 34915869]
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  • Sarah Snanoudj, Stéphanie Torre, Bénédicte Sudrié-Arnaud, Lenaig Abily-Donval, Alice Goldenberg, Gajja S Salomons, Stéphane Marret, Soumeya Bekri, Abdellah Tebani. Heterogenous Clinical Landscape in a Consanguineous Malonic Aciduria Family. International journal of molecular sciences. 2021 Nov; 22(23):. doi: 10.3390/ijms222312633. [PMID: 34884438]
  • Majid Alfadhel, Marwan Nashabat, Mohammed Saleh, Mohammed Elamin, Ahmed Alfares, Ali Al Othaim, Muhammad Umair, Hind Ahmed, Faroug Ababneh, Fuad Al Mutairi, Wafaa Eyaid, Abdulrahman Alswaid, Lina Alohali, Eissa Faqeih, Mohammed Almannai, Majed Aljeraisy, Bayan Albdah, Mohamed A Hussein, Zuhair Rahbeeni, Ali Alasmari. Long-term effectiveness of carglumic acid in patients with propionic acidemia (PA) and methylmalonic acidemia (MMA): a randomized clinical trial. Orphanet journal of rare diseases. 2021 10; 16(1):422. doi: 10.1186/s13023-021-02032-8. [PMID: 34635114]
  • Ching-Ti Liu, David Karasik, Hanfei Xu, Yanhua Zhou, Kerry Broe, L Adrienne Cupples, Lisette Cpgm de Groot, Annelies Ham, Marian T Hannan, Yi-Hsiang Hsu, Paul Jacques, Robert R McLean, Ligi Paul, Jacob Selhub, Katerina Trajanoska, Nathalie van der Velde, Natasja van Schoor, Douglas P Kiel. Genetic variants modify the associations of concentrations of methylmalonic acid, vitamin B-12, vitamin B-6, and folate with bone mineral density. The American journal of clinical nutrition. 2021 08; 114(2):578-587. doi: 10.1093/ajcn/nqab093. [PMID: 33964857]
  • Alphons J M Vermorken, Jingjing Zhu, Paul Holvoet, Yali Cui. The marker of cobalamin deficiency, plasma methylmalonic acid, may help identifying lysosomal iron trapping in patients. Its possible utility for heart failure. Redox biology. 2021 08; 44(?):102011. doi: 10.1016/j.redox.2021.102011. [PMID: 34049219]
  • Irini Manoli, Alexandra R Pass, Elizabeth A Harrington, Jennifer L Sloan, Jack Gagné, Samantha McCoy, Sarah L Bell, Jacob D Hattenbach, Brooks P Leitner, Courtney J Duckworth, Laura A Fletcher, Thomas M Cassimatis, Carolina I Galarreta, Audrey Thurm, Joseph Snow, Carol Van Ryzin, Susan Ferry, Nicholas Ah Mew, Oleg A Shchelochkov, Kong Y Chen, Charles P Venditti. 1-13C-propionate breath testing as a surrogate endpoint to assess efficacy of liver-directed therapies in methylmalonic acidemia (MMA). Genetics in medicine : official journal of the American College of Medical Genetics. 2021 08; 23(8):1522-1533. doi: 10.1038/s41436-021-01143-8. [PMID: 33820958]
  • R X He, H Dong, H W Zhang, Y Zhang, L L Kang, H Li, M Shen, R Mo, J Q Song, Y P Liu, Z H Chen, Y Liu, Y Jin, M Q Li, H Zheng, D X Li, J Qin, H F Zhang, M Huang, R X Zheng, D S Liang, Y P Tian, H X Yao, Y L Yang. [Clinical and genetic studies on 76 patients with hydrocephalus caused by methylmalonic acidemia combined with homocysteinuria]. Zhonghua er ke za zhi = Chinese journal of pediatrics. 2021 Jun; 59(6):459-465. doi: 10.3760/cma.j.cn112140-20210311-00204. [PMID: 34102818]
  • Andrew McCaddon, Björn Regland. COVID-19: A methyl-group assault?. Medical hypotheses. 2021 Apr; 149(?):110543. doi: 10.1016/j.mehy.2021.110543. [PMID: 33657459]
  • Mona Synnøve Bjune, Carine Lindquist, Marit Hallvardsdotter Stafsnes, Bodil Bjørndal, Per Bruheim, Thomas A Aloysius, Ottar Nygård, Jon Skorve, Lise Madsen, Simon N Dankel, Rolf Kristian Berge. Plasma 3-hydroxyisobutyrate (3-HIB) and methylmalonic acid (MMA) are markers of hepatic mitochondrial fatty acid oxidation in male Wistar rats. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2021 04; 1866(4):158887. doi: 10.1016/j.bbalip.2021.158887. [PMID: 33454435]
  • Aylin Yetim, Erhan Aygün, Çağcıl Yetim, Ahmet Ucar, Zeynep Karakaş, Gülden Gökçay, Mübeccel Demirkol, Beyhan Ömer, Gülbin Gökçay, Firdevs Baş, Ethem Erginöz, Türkan Dağoğlu. Measurement of serum vitamin B12-related metabolites in newborns: implications for new cutoff values to detect B12 deficiency. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians. 2021 Apr; 34(8):1260-1268. doi: 10.1080/14767058.2019.1633301. [PMID: 31204544]
  • Pooja Dhiman, Raji Ramachandran Pillai, Anand Babu Wilson, Nancy Premkumar, Balaji Bharadwaj, Veena P Ranjan, Soundravally Rajendiran. Cross-sectional association between vitamin B12 status and probable postpartum depression in Indian women. BMC pregnancy and childbirth. 2021 Feb; 21(1):146. doi: 10.1186/s12884-021-03622-x. [PMID: 33596868]
  • Rajdeep Kaur, Savita Verma Attri, Arushi Gahlot Saini, Naveen Sankhyan. A high frequency and geographical distribution of MMACHC R132* mutation in children with cobalamin C defect. Amino acids. 2021 Feb; 53(2):253-264. doi: 10.1007/s00726-021-02942-8. [PMID: 33515116]
  • Manal Mohammed Hashem, Ahmed Esmael, Abdelfattah Kasem Nassar, Mohammed El-Sherif. The relationship between exacerbated diabetic peripheral neuropathy and metformin treatment in type 2 diabetes mellitus. Scientific reports. 2021 01; 11(1):1940. doi: 10.1038/s41598-021-81631-8. [PMID: 33479439]
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  • Friederike Hörster, Ali Tunç Tuncel, Florian Gleich, Tanja Plessl, Sean D Froese, Sven F Garbade, Stefan Kölker, Matthias R Baumgartner. Delineating the clinical spectrum of isolated methylmalonic acidurias: cblA and mut. Journal of inherited metabolic disease. 2021 01; 44(1):193-214. doi: 10.1002/jimd.12297. [PMID: 32754920]
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  • Ineke J Riphagen, Isidor Minović, Dion Groothof, Adrian Post, Manfred L Eggersdorfer, Jenny E Kootstra-Ros, Martin H de Borst, Gerjan Navis, Frits A J Muskiet, Ido P Kema, M Rebecca Heiner-Fokkema, Stephan J L Bakker. Methylmalonic acid, vitamin B12, renal function, and risk of all-cause mortality in the general population: results from the prospective Lifelines-MINUTHE study. BMC medicine. 2020 12; 18(1):380. doi: 10.1186/s12916-020-01853-x. [PMID: 33298054]
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  • Rihwa Choi, Youngju Oh, Mi-Jung Park, Serim Kim, Youngrae Kim, Sang Gon Lee, Eun Hee Lee. Test utilization for the diagnosis of vitamin B12 and folate deficiency in local clinics in Korea. Journal of clinical laboratory analysis. 2020 Nov; 34(11):e23441. doi: 10.1002/jcla.23441. [PMID: 33156552]
  • Araceli Jarquin Campos, Lorenz Risch, Urs Nydegger, Jacobo Wiesner, Maclovia V Van Dyck, Christoph Seger, Zeno Stanga, Harald Renz, Martin Risch. Diagnostic Characteristics of 3-Parameter and 2-Parameter Equations for the Calculation of a Combined Indicator of Vitamin B12 Status to Predict Cobalamin Deficiency in a Large Mixed Patient Population. Clinical laboratory. 2020 Oct; 66(10):. doi: 10.7754/clin.lab.2020.200130. [PMID: 33073953]
  • Ru-Yue Chen, Xiao-Zhong Li, Qiang Lin, Yun Zhu, Yun-Yan Shen, Qin-Ying Xu, Xue-Ming Zhu, Lin-Qi Chen, Hai-Ying Wu, Xu-Qin Chen. Proteinuria as a presenting sign of combined methylmalonic acidemia and homocysteinemia: case report. BMC medical genetics. 2020 09; 21(1):183. doi: 10.1186/s12881-020-01122-x. [PMID: 32957924]
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  • Ana P Gomes, Didem Ilter, Vivien Low, Jennifer E Endress, Juan Fernández-García, Adam Rosenzweig, Tanya Schild, Dorien Broekaert, Adnan Ahmed, Melanie Planque, Ilaria Elia, Julie Han, Charles Kinzig, Edouard Mullarky, Anders P Mutvei, John Asara, Rafael de Cabo, Lewis C Cantley, Noah Dephoure, Sarah-Maria Fendt, John Blenis. Age-induced accumulation of methylmalonic acid promotes tumour progression. Nature. 2020 09; 585(7824):283-287. doi: 10.1038/s41586-020-2630-0. [PMID: 32814897]
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