Acetaldehyde (BioDeep_00000004377)

 

Secondary id: BioDeep_00000405408

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Acetic aldehyde

化学式: C2H4O (44.0262)
中文名称: 乙醛-13C2, 乙醛
谱图信息: 最多检出来源 Homo sapiens(blood) 32.17%

分子结构信息

SMILES: CC=O
InChI: InChI=1S/C2H4O/c1-2-3/h2H,1H3

描述信息

Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol which is mediated by the enzyme alcohol dehydrogenase 1B. Acetaldehyde can also be converted to acetic acid by the enzyme aldehyde dehydrogenase (mitochondrial) and aldehyde dehydrogenase X (mitochondrial). The main method of production is the oxidation of ethylene by the Wacker process, which involves oxidation of ethylene using a homogeneous palladium/copper system: 2 CH2CH2 + O2 → 2 CH3CHO. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually. In humans, acetaldehyde is involved in disulfiram action pathway. Acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Outside of the human body, acetaldehyde is found, on average, in the highest concentration in a few different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine) and in a lower concentration in . acetaldehyde has also been detected, but not quantified in several different foods, such as malabar plums, malus (crab apple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. In condensation reactions, acetaldehyde is prochiral. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and crohns disease; also acetaldehyde has been linked to the inborn metabolic disorders including aldehyde dehydrogenase deficiency (III) sulfate is used to reoxidize the mercury back to the mercury. Acetaldehyde was first observed by the Swedish pharmacist/chemist Carl Wilhelm Scheele (1774); it was then investigated by the French chemists Antoine François, comte de Fourcroy and Louis Nicolas Vauquelin (1800), and the German chemists Johann Wolfgang Döbereiner (1821, 1822, 1832) and Justus von Liebig (1835). At room temperature, acetaldehyde (CH3CHO) is more stable than vinyl alcohol (CH2CHOH) by 42.7 kJ/mol: Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. The water industry generally recognizes 20–40 ppb as the taste/odor threshold for acetaldehyde. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity.
Flavouring agent and adjuvant used to impart orange, apple and butter flavours; component of food flavourings added to milk products, baked goods, fruit juices, candy, desserts and soft drinks [DFC]

同义名列表

11 个代谢物同义名

Acetic aldehyde; Ethyl aldehyde; Acetaldehydes; acetaldehyde; Acetaldehyd; Azetaldehyd; Aldehyde; Ethanal; ch3cho; Acetaldehyde; Acetaldehyde



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(21)

BioCyc(40)

PlantCyc(1)

代谢反应

1473 个相关的代谢反应过程信息。

Reactome(214)

BioCyc(372)

WikiPathways(5)

Plant Reactome(296)

INOH(2)

PlantCyc(527)

COVID-19 Disease Map(1)

PathBank(56)

PharmGKB(0)

40 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 9 ALB, AOX1, BCL2, CAT, CYP2E1, ELANE, NFE2L2, TUBB4B, XDH
Peripheral membrane protein 4 ACHE, CYP1B1, CYP2E1, HSD17B6
Endosome membrane 1 TF
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, CYP2E1
Nucleus 6 ACHE, ALB, BCL2, MPO, NFE2L2, TUBB4B
cytosol 12 ADH1B, ADH1C, AKR1A1, ALB, AOX1, BCL2, CAT, ELANE, GSR, NFE2L2, TUBB4B, XDH
phagocytic vesicle 1 ELANE
centrosome 2 ALB, NFE2L2
nucleoplasm 5 ADH1B, ADH1C, ATP2B1, MPO, NFE2L2
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 2 ACHE, ATP2B1
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 ATP2B1
Synapse 3 ACHE, AKR1A1, ATP2B1
cell surface 3 ACHE, ELANE, TF
glutamatergic synapse 1 ATP2B1
Golgi apparatus 3 ACHE, ALB, NFE2L2
mitochondrial inner membrane 1 CYP2E1
neuromuscular junction 1 ACHE
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 2 AKR1A1, NFE2L2
Lysosome 1 MPO
plasma membrane 6 ACHE, ADH1B, ADH1C, ATP2B1, NFE2L2, TF
synaptic vesicle membrane 1 ATP2B1
Membrane 5 ACHE, ATP2B1, BCL2, CAT, CYP1B1
apical plasma membrane 2 AKR1A1, TF
basolateral plasma membrane 1 ATP2B1
extracellular exosome 10 AKR1A1, ALB, AOX1, ATP2B1, CAT, ELANE, GSR, MPO, TF, TUBB4B
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 ALB, BCL2, HSD17B6
extracellular space 8 ACHE, AKR1A1, ALB, CXCL8, ELANE, MPO, TF, XDH
perinuclear region of cytoplasm 2 ACHE, TF
mitochondrion 4 BCL2, CAT, CYP1B1, GSR
protein-containing complex 3 ALB, BCL2, CAT
intracellular membrane-bounded organelle 6 ATP2B1, CAT, CYP1B1, CYP2E1, HSD17B6, MPO
Microsome membrane 3 CYP1B1, CYP2E1, HSD17B6
Secreted 4 ACHE, ALB, CXCL8, TF
extracellular region 8 ACHE, ALB, CAT, CXCL8, ELANE, MPO, TF, TUBB4B
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
basal part of cell 1 TF
mitochondrial matrix 2 CAT, GSR
Extracellular side 1 ACHE
anchoring junction 1 ALB
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 GSR
Extracellular vesicle 1 TUBB4B
cytoplasmic vesicle 1 TF
microtubule cytoskeleton 1 TUBB4B
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 1 TF
vesicle 1 TF
Apical cell membrane 1 AKR1A1
Mitochondrion inner membrane 1 CYP2E1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 1 CAT
microtubule 1 TUBB4B
Peroxisome 2 CAT, XDH
basement membrane 1 ACHE
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ELANE
secretory granule 2 ELANE, MPO
lateral plasma membrane 1 ATP2B1
Late endosome 1 TF
ciliary basal body 1 ALB
chromatin 1 NFE2L2
mediator complex 1 NFE2L2
cell projection 1 ATP2B1
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 2 ALB, TF
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
axonemal microtubule 1 TUBB4B
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 ACHE
myelin sheath 1 BCL2
basal plasma membrane 1 TF
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 2 ALB, TF
transcription repressor complex 1 ELANE
platelet alpha granule lumen 1 ALB
specific granule lumen 1 ELANE
endocytic vesicle 1 TF
azurophil granule lumen 3 ELANE, MPO, TUBB4B
immunological synapse 1 ATP2B1
clathrin-coated endocytic vesicle membrane 1 TF
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
protein-DNA complex 1 NFE2L2
Cytoplasmic vesicle, phagosome 1 ELANE
vesicle coat 1 TF
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
[Isoform H]: Cell membrane 1 ACHE
ciliary transition fiber 1 ALB
dense body 1 TF


文献列表

  • Meiyue Qiu, Lili Yang, Zhiqiang Jiang, Yu Chen, Qinxin Liu, Xia Wang, Weidong Qu. Mixed exposure to haloacetaldehyde disinfection by-products exacerbates lipid aggregation in the liver of mice. Environmental pollution (Barking, Essex : 1987). 2024 Jun; 350(?):123971. doi: 10.1016/j.envpol.2024.123971. [PMID: 38641033]
  • Héléna Alamil, Marie-Lise Colsoul, Natacha Heutte, Marie Van Der Schueren, Laurence Galanti, Mathilde Lechevrel. Exocyclic DNA adducts and oxidative stress parameters: useful tools for biomonitoring exposure to aldehydes in smokers. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2024 May; 29(3):154-160. doi: 10.1080/1354750x.2024.2333361. [PMID: 38506499]
  • Pavel Pospíšil, Ankush Prasad, Julie Belková, Renuka Ramalingam Manoharan, Michaela Sedlářová. Formation of free acetaldehydes derived from lipid peroxidation in U937 monocyte-like cells. Biochimica et biophysica acta. General subjects. 2024 Feb; 1868(2):130527. doi: 10.1016/j.bbagen.2023.130527. [PMID: 38043915]
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  • Mengyun Xing, Kangkang Huang, Chen Zhang, Dujun Xi, Huifeng Luo, Jiabo Pei, Ruoxin Ruan, Hui Liu. Transcriptome Analysis Reveals the Molecular Mechanism and Responsive Genes of Waterlogging Stress in Actinidia deliciosa Planch Kiwifruit Plants. International journal of molecular sciences. 2023 Nov; 24(21):. doi: 10.3390/ijms242115887. [PMID: 37958870]
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  • Tomoya Kitakaze, Masako Inoue, Hitoshi Ashida. Aged Garlic Extract Prevents Alcohol-Induced Cytotoxicity through Induction of Aldehyde Dehydrogenase 2 in the Liver of Mice. Molecular nutrition & food research. 2023 Mar; ?(?):e2200627. doi: 10.1002/mnfr.202200627. [PMID: 36856009]
  • Kyeong Jin Kim, Soo-Yeon Park, Tae Gwon Park, Hyeon-Ju Park, Young-Jun Kim, Eun Ji Kim, Wonsuk Shin, Anhye Kim, Hyounggyoon Yoo, MinSon Kweon, Jihwan Jang, Su-Young Choi, Ji Yeon Kim. Noni fruit extract ameliorates alcohol-induced hangover symptoms by reducing the concentrations of alcohol and acetaldehyde in a Sprague Dawley rat model and a human intervention study. Food & function. 2023 Feb; 14(3):1750-1760. doi: 10.1039/d2fo02835b. [PMID: 36727425]
  • Mayrel Palestino-Domínguez, Alejandro Escobedo-Calvario, Soraya Salas-Silva, Moises Vergara-Mendoza, Veronica Souza-Arroyo, Roberto Lazzarini, Roxana Miranda-Labra, Leticia Bucio-Ortiz, María Concepción Gutiérrez-Ruiz, Luis E Gomez-Quiroz. Erk1/2 signaling mediates the HGF-induced protection against ethanol and acetaldehyde-induced toxicity in the pancreatic RINm5F cell line. Journal of biochemical and molecular toxicology. 2023 Jan; ?(?):e23302. doi: 10.1002/jbt.23302. [PMID: 36636782]
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  • Gerhard Eisenbrand, Matthias Baum, Alexander T Cartus, Patrick Diel, Karl-Heinz Engel, Barbara Engeli, Bernd Epe, Tilman Grune, Sabine Guth, Dirk Haller, Volker Heinz, Michael Hellwig, Jan G Hengstler, Thomas Henle, Hans-Ulrich Humpf, Henry Jäger, Hans-Georg Joost, Sabine Kulling, Dirk W Lachenmeier, Alfonso Lampen, Marcel Leist, Angela Mally, Doris Marko, Ute Nöthlings, Elke Röhrdanz, Angelika Roth, Joachim Spranger, Richard Stadler, Stefan Vieths, Wim Wätjen, Pablo Steinberg. Salivary nitrate/nitrite and acetaldehyde in humans: potential combination effects in the upper gastrointestinal tract and possible consequences for the in vivo formation of N-nitroso compounds-a hypothesis. Archives of toxicology. 2022 06; 96(6):1905-1914. doi: 10.1007/s00204-022-03296-0. [PMID: 35504979]
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