(2R,3S)-2-methylcitric acid (BioDeep_00001884385)
natural product
代谢物信息卡片
(2R,3S)-2-methylcitric acid
化学式: C7H10O7 (206.0427)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI: InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t3-,7-/m1/s1
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:30836
- PubChem: 439681
- CAS: 64815-79-8
- MetaboLights: MTBLC30836
- LOTUS: LTS0073454
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)
5 个相关的物种来源信息
- 2 - Bacteria: LTS0073454
- 1236 - Gammaproteobacteria: LTS0073454
- 135621 - Pseudomonadaceae: LTS0073454
- 286 - Pseudomonas: LTS0073454
- 287 - Pseudomonas aeruginosa: LTS0073454
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
- Jiaqi Sun, Jun Ding, Qingsong Shen, Xiyang Wang, Min Wang, Yongping Huang, Xuechun Zhang, Huan Zhu, Feng Zhang, Dongde Wu, Min Peng, Zhonglin Zhang, Yufeng Yuan, Wenhua Li, Zhi-Gang She, Xiao-Jing Zhang, Hongliang Li, Peng Zhang, Zan Huang. Decreased propionyl-CoA metabolism facilitates metabolic reprogramming and promotes hepatocellular carcinoma.
Journal of hepatology.
2023 Mar; 78(3):627-642. doi:
10.1016/j.jhep.2022.11.017. [PMID: 36462680] - Michelle R Denburg, Yunwen Xu, Alison G Abraham, Josef Coresh, Jingsha Chen, Morgan E Grams, Harold I Feldman, Paul L Kimmel, Casey M Rebholz, Eugene P Rhee, Ramachandran S Vasan, Bradley A Warady, Susan L Furth. Metabolite Biomarkers of CKD Progression in Children.
Clinical journal of the American Society of Nephrology : CJASN.
2021 08; 16(8):1178-1189. doi:
10.2215/cjn.00220121. [PMID: 34362785] - Evelina Maines, Giulio Catesini, Sara Boenzi, Antonella Mosca, Manila Candusso, Luca Dello Strologo, Diego Martinelli, Arianna Maiorana, Alessandra Liguori, Giorgia Olivieri, Roberta Taurisano, Fiorella Piemonte, Cristiano Rizzo, Marco Spada, Carlo Dionisi-Vici. Plasma methylcitric acid and its correlations with other disease biomarkers: The impact in the follow up of patients with propionic and methylmalonic acidemia.
Journal of inherited metabolic disease.
2020 11; 43(6):1173-1185. doi:
10.1002/jimd.12287. [PMID: 32681732] - Osama Y Al-Dirbashi, Charu Sharma, Nahid Al Dahouri, Anas Al Aidaros, Shamma Al-Muhairi, Rami Beiram, Salah Gariballa, Juma Al Kaabi. Role of Functional Biomarkers to Identify Early Vitamin B12 Deficiency in Patients with Sleeve Gastrectomy: A Cross-Sectional Study.
Medicina (Kaunas, Lithuania).
2020 Mar; 56(3):. doi:
10.3390/medicina56030142. [PMID: 32245061] - Joanne F Dorgan, Seungyoun Jung, Cher M Dallal, Min Zhan, Christina A Stennett, Yuji Zhang, Richard L Eckert, Linda G Snetselaar, Linda Van Horn. Alcohol consumption and serum metabolite concentrations in young women.
Cancer causes & control : CCC.
2020 Feb; 31(2):113-126. doi:
10.1007/s10552-019-01256-1. [PMID: 31828464] - Agnese Serafini, Lendl Tan, Stuart Horswell, Steven Howell, Daniel J Greenwood, Deborah M Hunt, Minh-Duy Phan, Mark Schembri, Mercedes Monteleone, Christine R Montague, Warwick Britton, Acely Garza-Garcia, Ambrosius P Snijders, Brian VanderVen, Maximiliano G Gutierrez, Nicholas P West, Luiz Pedro S de Carvalho. Mycobacterium tuberculosis requires glyoxylate shunt and reverse methylcitrate cycle for lactate and pyruvate metabolism.
Molecular microbiology.
2019 10; 112(4):1284-1307. doi:
10.1111/mmi.14362. [PMID: 31389636] - Nahid Al Dhahouri, Claus-Dieter Langhans, Zalikha Al Hammadi, Jürgen G Okun, Georg F Hoffmann, Fatma Al-Jasmi, Osama Y Al-Dirbashi. Quantification of methylcitrate in dried urine spots by liquid chromatography tandem mass spectrometry for the diagnosis of propionic and methylmalonic acidemias.
Clinica chimica acta; international journal of clinical chemistry.
2018 Dec; 487(?):41-45. doi:
10.1016/j.cca.2018.09.017. [PMID: 30217751] - Hafsa Majid, Lena Jafri, Aysha Habib Khan, Zeba Zulfiqar Ali, Azeema Jamil, Nasir Yusufzai, Midhat Fatimah, Bushra Afroze. Diagnostic dilemma of patients with methylmalonic aciduria: Experience from a tertiary care centre in Pakistan.
JPMA. The Journal of the Pakistan Medical Association.
2018 Apr; 68(4):510-514. doi:
NULL. [PMID: 29808036] - Nicola Longo, Leisa B Price, Eduard Gappmaier, Nancy L Cantor, Sharon L Ernst, Carrie Bailey, Marzia Pasquali. Anaplerotic therapy in propionic acidemia.
Molecular genetics and metabolism.
2017 09; 122(1-2):51-59. doi:
10.1016/j.ymgme.2017.07.003. [PMID: 28712602] - Lianshu Han, Shengnan Wu, Jun Ye, Wenjuan Qiu, Huiwen Zhang, Xiaolan Gao, Yu Wang, Zhuwen Gong, Jing Jin, Xuefan Gu. Biochemical, molecular and outcome analysis of eight chinese asymptomatic individuals with methyl malonic acidemia detected through newborn screening.
American journal of medical genetics. Part A.
2015 Oct; 167A(10):2300-5. doi:
10.1002/ajmg.a.37147. [PMID: 25982642] - Mukesh K Dubey, Anders Broberg, Dan Funck Jensen, Magnus Karlsson. Role of the methylcitrate cycle in growth, antagonism and induction of systemic defence responses in the fungal biocontrol agent Trichoderma atroviride.
Microbiology (Reading, England).
2013 Dec; 159(Pt 12):2492-2500. doi:
10.1099/mic.0.070466-0. [PMID: 24100269] - Paris Jafari, Olivier Braissant, Petra Zavadakova, Hugues Henry, Luisa Bonafé, Diana Ballhausen. Brain damage in methylmalonic aciduria: 2-methylcitrate induces cerebral ammonium accumulation and apoptosis in 3D organotypic brain cell cultures.
Orphanet journal of rare diseases.
2013 Jan; 8(?):4. doi:
10.1186/1750-1172-8-4. [PMID: 23298464] - Swarnalee Dutta, T Swaroopa Rani, Appa Rao Podile. Root exudate-induced alterations in Bacillus cereus cell wall contribute to root colonization and plant growth promotion.
PloS one.
2013; 8(10):e78369. doi:
10.1371/journal.pone.0078369. [PMID: 24205213] - Mureo Kasahara, Seisuke Sakamoto, Hiroyuki Kanazawa, Chiaki Karaki, Toshihiko Kakiuchi, Takanobu Shigeta, Akinari Fukuda, Rika Kosaki, Atsuko Nakazawa, Mika Ishige, Masayoshi Nagao, Yosuke Shigematsu, Tohru Yorifuji, Yasuhiro Naiki, Reiko Horikawa. Living-donor liver transplantation for propionic acidemia.
Pediatric transplantation.
2012 May; 16(3):230-4. doi:
10.1111/j.1399-3046.2011.01607.x. [PMID: 22151065] - Sara R Zwart, C Robert Gibson, Thomas H Mader, Karen Ericson, Robert Ploutz-Snyder, Martina Heer, Scott M Smith. Vision changes after spaceflight are related to alterations in folate- and vitamin B-12-dependent one-carbon metabolism.
The Journal of nutrition.
2012 Mar; 142(3):427-31. doi:
10.3945/jn.111.154245. [PMID: 22298570] - Randy J Chandler, Suma Chandrasekaran, Nuria Carrillo-Carrasco, Julien S Senac, Sean E Hofherr, Michael A Barry, Charles P Venditti. Adeno-associated virus serotype 8 gene transfer rescues a neonatal lethal murine model of propionic acidemia.
Human gene therapy.
2011 Apr; 22(4):477-81. doi:
10.1089/hum.2010.164. [PMID: 20950151] - Seung-Ho Lee, You-Kyoung Han, Sung-Hwan Yun, Yin-Won Lee. Roles of the glyoxylate and methylcitrate cycles in sexual development and virulence in the cereal pathogen Gibberella zeae.
Eukaryotic cell.
2009 Aug; 8(8):1155-64. doi:
10.1128/ec.00335-08. [PMID: 19525419] - Yao Zhang, Yan-ling Yang, Yuki Hasegawa, Seiji Yamaguchi, Chun-yan Shi, Jin-qing Song, Sujan Sayami, Ping Liu, Rong Yan, Jin-hua Dong, Jiong Qin. Prenatal diagnosis of methylmalonic aciduria by analysis of organic acids and total homocysteine in amniotic fluid.
Chinese medical journal.
2008 Feb; 121(3):216-9. doi:
. [PMID: 18298912] - Hanna Krawczyk, Tomasz Martyniuk. Characterisation of the 1H and 13C NMR spectra of methylcitric acid.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2007 Jun; 67(2):298-305. doi:
10.1016/j.saa.2006.07.017. [PMID: 16997619] - H Krawczyk, W Gradowska. 1H NMR spectra of methylcitric acid in urine.
Journal of inherited metabolic disease.
2007 Apr; 30(2):263. doi:
10.1007/s10545-007-0420-6. [PMID: 17295121] - C D Campbell, J Ganesh, C Ficicioglu. Two newborns with nutritional vitamin B12 deficiency: challenges in newborn screening for vitamin B12 deficiency.
Haematologica.
2005 Dec; 90(12 Suppl):ECR45. doi:
. [PMID: 16464760] - Stefan Kölker, Marina Schwab, Friederike Hörster, Sven Sauer, Angela Hinz, Nicole I Wolf, Ertan Mayatepek, Georg F Hoffmann, Jan A M Smeitink, Jürgen G Okun. Methylmalonic acid, a biochemical hallmark of methylmalonic acidurias but no inhibitor of mitochondrial respiratory chain.
The Journal of biological chemistry.
2003 Nov; 278(48):47388-93. doi:
10.1074/jbc.m308861200. [PMID: 12972416] - Martin Busch, Günter Stein, Wolfgang Poppitz, Gert Hein, Andreas Müller. Validated capillary gas chromatographic-mass spectrometric assay to determine 2-methylcitric acid I and II levels in human serum by using a pulsed splitless injection procedure.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Aug; 775(2):215-23. doi:
10.1016/s1570-0232(02)00293-3. [PMID: 12113988] - Jürgen G Okun, Friederike Hörster, Lilla M Farkas, Patrik Feyh, Angela Hinz, Sven Sauer, Georg F Hoffmann, Klaus Unsicker, Ertan Mayatepek, Stefan Kölker. Neurodegeneration in methylmalonic aciduria involves inhibition of complex II and the tricarboxylic acid cycle, and synergistically acting excitotoxicity.
The Journal of biological chemistry.
2002 Apr; 277(17):14674-80. doi:
10.1074/jbc.m200997200. [PMID: 11847233] - B F Henning, M Tepel, R Riezler, H J Naurath. Long-term effects of vitamin B(12), folate, and vitamin B(6) supplements in elderly people with normal serum vitamin B(12) concentrations.
Gerontology.
2001 Jan; 47(1):30-5. doi:
10.1159/000052767. [PMID: 11244289] - B F Henning, R Riezler, M Tepel, K Langer, H Raidt, U Graefe, W Zidek. Evidence of altered homocysteine metabolism in chronic renal failure.
Nephron.
1999; 83(4):314-22. doi:
10.1159/000045423. [PMID: 10575293] - R H Allen, S P Stabler, J Lindenbaum. Relevance of vitamins, homocysteine and other metabolites in neuropsychiatric disorders.
European journal of pediatrics.
1998 Apr; 157 Suppl 2(?):S122-6. doi:
10.1007/pl00014295. [PMID: 9587039] - G Scalabrino, F R Buccellato, G Tredici, A Morabito, E C Lorenzini, R H Allen, J Lindenbaum. Enhanced levels of biochemical markers for cobalamin deficiency in totally gastrectomized rats: uncoupling of the enhancement from the severity of spongy vacuolation in spinal cord.
Experimental neurology.
1997 Apr; 144(2):258-65. doi:
10.1006/exnr.1996.6376. [PMID: 9168827] - H J Naurath, E Joosten, R Riezler, S P Stabler, R H Allen, J Lindenbaum. Effects of vitamin B12, folate, and vitamin B6 supplements in elderly people with normal serum vitamin concentrations.
Lancet (London, England).
1995 Jul; 346(8967):85-9. doi:
10.1016/s0140-6736(95)92113-3. [PMID: 7603218] - R H Allen, S P Stabler, D G Savage, J Lindenbaum. Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency.
Metabolism: clinical and experimental.
1993 Aug; 42(8):978-88. doi:
10.1016/0026-0495(93)90010-l. [PMID: 8345822] - R E Kretschmer, C Bachmann. Methylcitric acid determination in amniotic fluid by electron-impact mass fragmentography.
Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie.
1988 May; 26(5):345-8. doi:
10.1515/cclm.1988.26.5.345. [PMID: 3404093] - D M Mock, D L Baswell, H Baker, R T Holman, L Sweetman. Biotin deficiency complicating parenteral alimentation: diagnosis, metabolic repercussions, and treatment.
The Journal of pediatrics.
1985 May; 106(5):762-9. doi:
10.1016/s0022-3476(85)80350-4. [PMID: 3923177] - L Sweetman, L Surh, H Baker, R M Peterson, W L Nyhan. Clinical and metabolic abnormalities in a boy with dietary deficiency of biotin.
Pediatrics.
1981 Oct; 68(4):553-8. doi:
. [PMID: 7322688]
