Isocitric acid (BioDeep_00000002693)

 

Secondary id: BioDeep_00000400037, BioDeep_00002053048

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid

化学式: C6H8O7 (192.0270018)
中文名称: DL-异柠檬酸三钠盐水合物, 异柠檬酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.15%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Isocitric acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/isocitric_acid (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002693). 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)O)C(=O)O)C(=O)O
InChI: InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)

描述信息

Isocitric acid, also known as isocitrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is a TCA (tricarboxylic acid) cycle intermediate. It is a structural isomer of citric acid and is formed from citrate with the help of the enzyme aconitase. More specifically, Isocitric acid is synthesized from citric acid via the intermediate cis-aconitic acid by the enzyme aconitase (aconitate hydratase). Isocitrate is acted upon by isocitrate dehydrogenase (IDH) to form alpha-ketoglutarate. This is a two-step process, which involves oxidation of isocitrate to oxalosuccinate (a ketone), followed by the decarboxylation of the carboxyl group beta to the ketone, forming alpha-ketoglutarate. In humans, IDH exists in three isoforms: IDH3 catalyzes the third step of the citric acid cycle while converting NAD+ to NADH in the mitochondria. The isoforms IDH1 and IDH2 catalyze the same reaction outside the context of the citric acid cycle and use NADP+ as a cofactor instead of NAD+. They localize to the cytosol as well as the mitochondrion and peroxisome. Isocitric acid exists in all living species, ranging from bacteria to plants to humans. Isocitric acid is a minor organic acid found in most fruit juices, especially in blackberries, youngberries, and boyberries, and in vegetables, especially in carrots. The determination of D-isocitric acid has become of importance in the analysis of fruit juices for the detection of illegal additives (adulteration). Since the quantities of citric and isocitric acids are correlated in fruit juices, a high ratio of citric to isocitric acid can indicate the addition of citric acid as an alduterant. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. Isocitric acid is mostly used in the food industry (food additive) as a food acidulant.
The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279) [HMDB]. Isocitric acid is found in many foods, some of which are wild carrot, redcurrant, carrot, and soursop.
[Spectral] Isocitrate (exact mass = 192.027) and CDP (exact mass = 403.01818) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions.

Isocitric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=320-77-4 (retrieved 2024-07-01) (CAS RN: 320-77-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3].
Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3].

同义名列表

28 个代谢物同义名

3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid; 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate; 1-Hydroxy-1,2,3-propanetricarboxylic acid; 1-Hydroxypropane-1,2,3-tricarboxylic acid; 1-Hydroxypropane-1,2,3-tricarboxylate; 1-Hydroxy-1,2,3-propanetricarboxylate; 3-Carboxy-2,3-dideoxy-pentaric acid; DL-Isocitric acid trisodium salt; 3-Carboxy-2,3-dideoxy-pentarate; Isocitric acid, potassium salt; Isocitric acid, trisodium salt; Isocitric acid, disodium salt; Isocitric acid, (11)C-labeled; Isocitric acid, calcium salt; 1-Hydroxytricarballylic acid; Isocitric acid, sodium salt; 1-Hydroxytricarballylate; Threo-D(S)-iso-citrate; Threo-DS-isocitrate; isocitric acid; D-Isocitrate; Iso-citrate; Isocitrate; I-cit; Isocitric acid; (1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylate; Isocitrate; Isocitric acid



数据库引用编号

40 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

61 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(5)

Plant Reactome(0)

INOH(5)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(49)

PharmGKB(0)

100 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

  • Zhaojun Nie, Linglu Wang, Peng Zhao, Zhenbo Wang, Qiuzhe Shi, Hongen Liu. Metabolomics reveals the impact of nitrogen combined with the zinc supply on zinc availability in calcareous soil via root exudates of winter wheat (Triticum aestivum). Plant physiology and biochemistry : PPB. 2023 Nov; 204(?):108069. doi: 10.1016/j.plaphy.2023.108069. [PMID: 37852066]
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  • Mònica Bulló, Christopher Papandreou, Jesus García-Gavilán, Miguel Ruiz-Canela, Jun Li, Marta Guasch-Ferré, Estefanía Toledo, Clary Clish, Dolores Corella, Ramon Estruch, Emilio Ros, Montserrat Fitó, Chih-Hao Lee, Kerry Pierce, Cristina Razquin, Fernando Arós, Lluís Serra-Majem, Liming Liang, Miguel A Martínez-González, Frank B Hu, Jordi Salas-Salvadó. Tricarboxylic acid cycle related-metabolites and risk of atrial fibrillation and heart failure. Metabolism: clinical and experimental. 2021 12; 125(?):154915. doi: 10.1016/j.metabol.2021.154915. [PMID: 34678258]
  • Kerri M Smith, Ian D Wilson, Paul D Rainville. Sensitive and Reproducible Mass Spectrometry-Compatible RP-UHPLC Analysis of Tricarboxylic Acid Cycle and Related Metabolites in Biological Fluids: Application to Human Urine. Analytical chemistry. 2021 01; 93(2):1009-1015. doi: 10.1021/acs.analchem.0c03863. [PMID: 33290053]
  • Lucas A Luna, Zachary Lesecq, Katharine A White, An Hoang, David A Scott, Olga Zagnitko, Andrey A Bobkov, Diane L Barber, Jamie M Schiffer, Daniel G Isom, Christal D Sohl. An acidic residue buried in the dimer interface of isocitrate dehydrogenase 1 (IDH1) helps regulate catalysis and pH sensitivity. The Biochemical journal. 2020 08; 477(16):2999-3018. doi: 10.1042/bcj20200311. [PMID: 32729927]
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  • Stein Hallan, Maryam Afkarian, Leila R Zelnick, Bryan Kestenbaum, Shoba Sharma, Rintaro Saito, Manjula Darshi, Gregory Barding, Daniel Raftery, Wenjun Ju, Matthias Kretzler, Kumar Sharma, Ian H de Boer. Metabolomics and Gene Expression Analysis Reveal Down-regulation of the Citric Acid (TCA) Cycle in Non-diabetic CKD Patients. EBioMedicine. 2017 Dec; 26(?):68-77. doi: 10.1016/j.ebiom.2017.10.027. [PMID: 29128444]
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