Isocitric acid (BioDeep_00000002693)

 

Secondary id: BioDeep_00000400037, BioDeep_00002053048

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


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

化学式: C6H8O7 (192.027)
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) 23.06%

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 2024-12-22) (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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 ACLY, ACO1, CAT, FH, G6PD, GLUL, IDH1, PC, PKM, TP53
Peripheral membrane protein 3 CYP11A1, G6PD, HSD17B6
Mitochondrion membrane 1 CYP11A1
Nucleus 6 CS, FH, GLUL, IDH3B, PKM, TP53
cytosol 14 ACLY, ACO1, ACO2, CAT, FH, G6PD, GLUL, GPT, GSR, IDH1, IDH2, PC, PKM, TP53
centrosome 1 TP53
nucleoplasm 2 ACLY, TP53
Cell membrane 1 GLUL
Lipid-anchor 1 GLUL
Early endosome membrane 1 HSD17B6
cell surface 1 EPO
Golgi apparatus 1 ACO1
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP11A1
Cytoplasm, cytosol 5 ACLY, ACO1, G6PD, GLUL, IDH1
plasma membrane 1 GLUL
Membrane 6 ACLY, CAT, CS, CYP11A1, G6PD, TP53
extracellular exosome 13 ACLY, ACO1, CAT, CS, EPO, FH, G6PD, GLUL, GPT, GSR, IDH1, IDH2, PKM
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 ACO1, GLUL, HSD17B6, TP53
extracellular space 2 EPO, INS
mitochondrion 14 ACO1, ACO2, CAT, CS, CYP11A1, FH, GLUL, GSR, IDH1, IDH2, IDH3B, PC, PKM, TP53
protein-containing complex 2 CAT, TP53
intracellular membrane-bounded organelle 3 CAT, G6PD, HSD17B6
Microsome membrane 1 HSD17B6
Secreted 2 EPO, INS
extracellular region 6 ACLY, CAT, EPO, IDH1, INS, PKM
cytoplasmic side of plasma membrane 1 G6PD
Mitochondrion matrix 3 CS, PC, TP53
mitochondrial matrix 10 ACO2, CAT, CS, CYP11A1, FH, GSR, IDH2, IDH3B, PC, TP53
transcription regulator complex 1 TP53
centriolar satellite 1 G6PD
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
external side of plasma membrane 1 GSR
Extracellular vesicle 1 PKM
nucleolus 1 TP53
vesicle 1 PKM
Mitochondrion inner membrane 1 CYP11A1
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 CAT
Peroxisome 3 CAT, IDH1, IDH2
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, IDH1
peroxisomal membrane 1 CAT
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 1 PKM
cilium 1 PKM
chromatin 1 TP53
Chromosome 1 FH
site of double-strand break 2 FH, TP53
endosome lumen 1 INS
cell body 2 EPO, GLUL
germ cell nucleus 1 TP53
replication fork 1 TP53
Microsome 1 GLUL
ficolin-1-rich granule lumen 4 ACLY, CAT, IDH1, PKM
secretory granule lumen 5 CAT, EPO, IDH1, INS, PKM
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
tertiary granule lumen 1 IDH1
transport vesicle 1 INS
azurophil granule lumen 1 ACLY
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
[Isoform 1]: Nucleus 1 TP53
Rough endoplasmic reticulum 1 PKM
isocitrate dehydrogenase complex (NAD+) 1 IDH3B
glial cell projection 1 GLUL
catalase complex 1 CAT
[Isoform Mitochondrial]: Mitochondrion 1 FH
[Isoform Cytoplasmic]: Cytoplasm, cytosol 1 FH
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM


文献列表

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