Aminoadipic acid (BioDeep_00000001297)

 

Secondary id: BioDeep_00000227599, BioDeep_00000398048, BioDeep_00000399892, BioDeep_00000405290, BioDeep_00000408272

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2S)-2-Azaniumyl-6-hydroxy-6-oxohexanoate

化学式: C6H11NO4 (161.0688)
中文名称: 2-氨基己二酸水合物, L-2-氨基己二酸, DL-α-氨基己二酸, 氨基己二酸, 2-氨基己二酸, L-α-氨基己二酸
谱图信息: 最多检出来源 Homo sapiens(plant) 13.93%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Aminoadipic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/aminoadipic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001297). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CC(C(=O)O)N)CC(=O)O
InChI: InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)

描述信息

Aminoadipic acid (CAS: 542-32-5), also known as 2-aminoadipate, is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117). Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293). Aging, diabetes, sepsis, and renal failure are known to catalyze the oxidation of lysyl residues to form 2-aminoadipic acid in human skin collagen and potentially other tissues (PMID: 18448817). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the three branched-chain amino acids: leucine, valine, and isoleucine) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes (PMID: 15389298). Long-term hyperglycemia of endothelial cells can also lead to elevated levels of aminoadipate which is thought to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526). 2-Aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic 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. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522).
A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA).

L-α-Aminoadipic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1118-90-7 (retrieved 2024-07-01) (CAS RN: 1118-90-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.

同义名列表

26 个代谢物同义名

(2S)-2-Azaniumyl-6-hydroxy-6-oxohexanoate; (2S)-2-Aminohexanedioic acid; (S)-2-Aminohexanedioic acid; L-2-Aminohexanedioic acid; L-alpha-Aminoadipic acid; 2-Aminohexanedioic acid; (S)-2-Aminohexanedioate; (S)-2-Aminoadipic acid; alpha-Aminoadipic acid; L-2-Aminohexanedioate; L-2-Aminoadipic acid; L-Α-aminoadipic acid; L-alpha-Aminoadipate; L-a-Aminoadipic acid; α-Aminoadipic acid; L-Aminoadipic acid; 2-Aminoadipic acid; L-Α-aminoadipate; L-a-Aminoadipate; L-2-Aminoadipate; Aminoadipic acid; 2-Aminoadipate; a-Aminoadipate; Aminoadipate; Aminoadipic acid; L-2-Aminoadipic acid



数据库引用编号

36 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

302 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(3)

Plant Reactome(272)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

78 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 AASS, CA1, CAT, GFAP, GLUL, MAPK14, SLC9A1, TH, VEGFA, VIM
Nucleus 8 AASS, ALDH7A1, GLUL, GRM1, MAPK14, MPO, TH, VEGFA
cytosol 9 AASS, ALDH7A1, CA1, CAT, GFAP, GLUL, MAPK14, TH, VIM
dendrite 2 GRM1, TH
phagocytic vesicle 1 VIM
nucleoplasm 3 MAPK14, MPO, SLC9A1
Cell membrane 6 GLUL, GRM1, SLC1A2, SLC9A1, TNF, VIM
Lipid-anchor 1 GLUL
lamellipodium 1 SLC9A1
Cell projection, axon 1 TH
Multi-pass membrane protein 3 GRM1, SLC1A2, SLC9A1
cell surface 4 SLC1A2, SLC9A1, TNF, VEGFA
glutamatergic synapse 3 GRM1, MAPK14, SLC1A2
Golgi apparatus 1 VEGFA
Golgi membrane 1 INS
neuronal cell body 1 TNF
presynaptic membrane 1 SLC1A2
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 1 GLUL
Lysosome 1 MPO
plasma membrane 6 GLUL, GRM1, SLC1A2, SLC9A1, TNF, VIM
terminal bouton 1 TH
Membrane 4 CAT, SLC1A2, SLC9A1, VEGFA
apical plasma membrane 1 SLC9A1
axon 2 TH, VIM
basolateral plasma membrane 1 SLC9A1
extracellular exosome 7 ALDH7A1, CA1, CAT, GLUL, MPO, SLC9A1, VIM
endoplasmic reticulum 2 GLUL, VEGFA
extracellular space 4 INS, MPO, TNF, VEGFA
perinuclear region of cytoplasm 2 SLC9A1, TH
Schaffer collateral - CA1 synapse 1 GRM1
adherens junction 1 VEGFA
intercalated disc 1 SLC9A1
mitochondrion 10 AADAT, AASS, ALDH7A1, CAT, DHTKD1, GCDH, GLUL, MAPK14, SLC9A1, TH
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 AASS, CAT, MPO
Secreted 2 INS, VEGFA
extracellular region 6 CAT, INS, MAPK14, MPO, TNF, VEGFA
cytoplasmic side of plasma membrane 1 TH
astrocyte end-foot 1 GFAP
Mitochondrion matrix 1 GCDH
mitochondrial matrix 6 AADAT, AASS, ALDH7A1, CAT, DHTKD1, GCDH
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
T-tubule 1 SLC9A1
perikaryon 1 TH
cytoplasmic vesicle 1 TH
Melanosome membrane 1 TH
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 SLC1A2
Cytoplasm, perinuclear region 1 TH
Membrane raft 3 SLC1A2, SLC9A1, TNF
Cytoplasm, cytoskeleton 1 VIM
focal adhesion 3 CAT, SLC9A1, VIM
axolemma 1 SLC1A2
extracellular matrix 1 VEGFA
Peroxisome 2 CAT, VIM
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 2 MPO, VEGFA
intermediate filament 2 GFAP, VIM
nuclear speck 1 MAPK14
Postsynaptic cell membrane 1 GRM1
neuron projection 2 TH, VIM
cell leading edge 1 VIM
cell projection 1 GFAP
phagocytic cup 1 TNF
cytoskeleton 1 VIM
[Isoform 1]: Mitochondrion 1 ALDH7A1
spindle pole 1 MAPK14
Basolateral cell membrane 1 SLC9A1
endosome lumen 1 INS
microtubule organizing center 1 VIM
[Isoform 2]: Cytoplasm, cytosol 1 ALDH7A1
cell body 3 GFAP, GLUL, SLC1A2
intermediate filament cytoskeleton 2 GFAP, VIM
azurophil granule 1 MPO
Microsome 1 GLUL
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
nuclear matrix 1 VIM
platelet alpha granule lumen 1 VEGFA
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 GRM1
Nucleus matrix 1 VIM
phagocytic vesicle lumen 1 MPO
astrocyte projection 1 SLC1A2
cytoplasmic side of lysosomal membrane 1 GFAP
glial cell projection 1 GLUL
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
neuron projection terminus 1 SLC1A2
oxoadipate dehydrogenase complex 1 DHTKD1
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
cation-transporting ATPase complex 1 SLC9A1
membrane protein complex 1 SLC1A2
G protein-coupled receptor dimeric complex 1 GRM1
G protein-coupled receptor homodimeric complex 1 GRM1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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