acetoacetate (BioDeep_00000228953)
human metabolite
代谢物信息卡片
化学式: C4H5O3- (101.02386800000001)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(natural_products) 4.26%
分子结构信息
SMILES: CC(=O)CC(=O)[O-]
InChI: InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1
描述信息
Acetoacetate, also known as acetoacetic acid or oxobutyrate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Acetoacetate is soluble (in water) and a weakly acidic compound (based on its pKa). Acetoacetate can be found in a number of food items such as plains prickly pear, daikon radish, papaya, and common chokecherry, which makes acetoacetate a potential biomarker for the consumption of these food products. Acetoacetic acid (also diacetic acid) is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid group, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid .
同义名列表
14 个代谢物同义名
Acetoacetic acid, calcium salt; Butanoic acid, 3-oxo-, ion(1-); Acetoacetic acid, lithium salt; Acetoacetic acid, sodium salt; Butanoate, 3-oxo-, ion(1-); Acetoacetic acid ion(1-); Acetoacetate ion(1-); Sodium acetoacetate; 3-Oxobutyric acid; acetoacetic acid; 3-Ketobutyrate; 3-Oxobutanoate; Acetoacetate; Oxobutyrate
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:13705
- PubChem: 6971017
- HMDB: HMDB0304256
- ChEMBL: CHEMBL2074691
- MetaCyc: 3-KETOBUTYRATE
- foodb: FDB030645
- chemspider: 5341896
- CAS: 141-81-1
分类词条
相关代谢途径
Reactome(7)
BioCyc(15)
- superpathway of sterol biosynthesis
- superpathway of L-lysine degradation
- L-lysine fermentation to acetate and butanoate
- isopropanol biosynthesis (engineered)
- acetone degradation III (to propane-1,2-diol)
- acetone degradation I (to methylglyoxal)
- acetone degradation II (to acetoacetate)
- superpathway of Clostridium acetobutylicum acidogenic and solventogenic fermentation
- pyruvate fermentation to acetone
- superpathway of Clostridium acetobutylicum solventogenic fermentation
- ketogenesis
- lysine fermentation to acetate and butyrate
- leucine degradation IV
- mevalonate degradation
- L-leucine degradation I
代谢反应
44 个相关的代谢反应过程信息。
Reactome(12)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Ketone body metabolism:
ACA + ATP + CoA-SH ⟶ ACA-CoA + AMP + PPi
- Synthesis of Ketone Bodies:
ACA + ATP + CoA-SH ⟶ ACA-CoA + AMP + PPi
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Synthesis of Ketone Bodies:
ACA + ATP + CoA-SH ⟶ ACA-CoA + AMP + PPi
- Ketone body metabolism:
ACA + ATP + CoA-SH ⟶ ACA-CoA + AMP + PPi
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Ketone body metabolism:
ACA + H+ + NADH ⟶ NAD + bHBA
- Synthesis of Ketone Bodies:
ACA + H+ + NADH ⟶ NAD + bHBA
BioCyc(29)
- acetone degradation III (to propane-1,2-diol):
NADP+ + propan-2-ol ⟶ H+ + NADPH + acetone
- acetone degradation I (to methylglyoxal):
NADP+ + propan-2-ol ⟶ H+ + NADPH + acetone
- superpathway of Clostridium acetobutylicum acidogenic and solventogenic fermentation:
H+ + acetoacetate ⟶ CO2 + acetone
- pyruvate fermentation to acetone:
H+ + acetoacetate ⟶ CO2 + acetone
- superpathway of Clostridium acetobutylicum solventogenic fermentation:
H+ + acetoacetate ⟶ CO2 + acetone
- ketogenesis:
H+ + acetoacetate ⟶ CO2 + acetone
- ketogenesis:
H+ + acetoacetate ⟶ CO2 + acetone
- ketogenesis:
H+ + acetoacetate ⟶ CO2 + acetone
- pyruvate fermentation to acetone:
acetoacetate + acetyl-CoA ⟶ acetate + acetoacetyl-CoA
- TCA cycle variation II:
2-oxoglutarate + an oxidized ferredoxin [iron-sulfur] cluster + coenzyme A ⟶ CO2 + a reduced ferredoxin [iron-sulfur] cluster + succinyl-CoA
- acetone degradation II (to acetoacetate):
NADP+ + propan-2-ol ⟶ H+ + NADPH + acetone
- ketogenesis:
H+ + acetoacetate ⟶ CO2 + acetone
- acetone degradation I (to methylglyoxal):
H+ + acetoacetate ⟶ CO2 + acetone
- isopropanol biosynthesis (engineered):
NADP+ + propan-2-ol ⟶ H+ + NADPH + acetone
- leucine degradation I:
2-oxoglutarate + leu ⟶ 4-methyl-2-oxopentanoate + glt
- superpathway of sterol biosynthesis:
4-methyl-2-oxopentanoate + NAD+ + coenzyme A ⟶ CO2 + NADH + isovaleryl-CoA
- leucine degradation I:
4-methyl-2-oxopentanoate + NAD+ + coenzyme A ⟶ CO2 + NADH + isovaleryl-CoA
- superpathway of L-lysine degradation:
acetoacetate + butanoyl-CoA ⟶ acetoacetyl-CoA + butanoate
- L-lysine fermentation to acetate and butanoate:
acetoacetate + butanoyl-CoA ⟶ acetoacetyl-CoA + butanoate
- lysine fermentation to acetate and butyrate:
L-3-aminobutyryl-CoA ⟶ H+ + ammonia + crotonyl-CoA
- glycerol degradation to butanol:
NAD+ + glycerol ⟶ H+ + NADH + dihydroxyacetone
- lysine fermentation to acetate and butyrate:
ATP + acetate ⟶ ADP + acetyl phosphate
- L-lysine fermentation to acetate and butanoate:
ATP + acetate ⟶ ADP + acetyl phosphate
- lysine fermentation to acetate and butyrate:
(3S,5S)-3,5-diaminohexanoate + H2O + NAD+ ⟶ (S)-5-amino-3-oxohexanoate + H+ + NADH + ammonia
- glycerol degradation to butanol:
NAD+ + glycerol ⟶ H+ + NADH + dihydroxyacetone
- lysine fermentation to acetate and butyrate:
L-3-aminobutyryl-CoA ⟶ H+ + ammonia + crotonyl-CoA
- glycerol degradation to butanol:
NAD+ + glycerol ⟶ H+ + NADH + dihydroxyacetone
- mevalonate degradation:
HMG-CoA ⟶ acetoacetate + acetyl-CoA
- L-leucine degradation I:
3-methylcrotonyl-CoA + ATP + hydrogencarbonate ⟶ 3-methylglutaconyl-CoA + ADP + H+ + phosphate
Plant Reactome(0)
INOH(0)
PlantCyc(2)
- ketogenesis:
(R)-3-hydroxybutanoate + NAD+ ⟶ H+ + NADH + acetoacetate
- ketogenesis:
(R)-3-hydroxybutanoate + NAD+ ⟶ H+ + NADH + acetoacetate
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Xiangyu Liu, Bo Zhang, Junsheng Tian, Yumei Han. Plasma metabolomics reveals the intervention mechanism of different types of exercise on chronic unpredictable mild stress-induced depression rat model.
Metabolic brain disease.
2024 Jan; 39(1):1-13. doi:
10.1007/s11011-023-01310-7
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Advanced science (Weinheim, Baden-Wurttemberg, Germany).
2023 Jun; ?(?):e2300032. doi:
10.1002/advs.202300032
. [PMID: 37382194] - Angeliki M Angelidi, Alexander Kokkinos, Despina Sanoudou, Margery A Connelly, Andreas Alexandrou, Geltrude Mingrone, Christos S Mantzoros. Early metabolomic, lipid and lipoprotein changes in response to medical and surgical therapeutic approaches to obesity.
Metabolism: clinical and experimental.
2023 01; 138(?):155346. doi:
10.1016/j.metabol.2022.155346
. [PMID: 36375643] - Xiao-Jun Wu, Qin-Qin Shu, Bin Wang, Lan Dong, Bin Hao. Acetoacetate Improves Memory in Alzheimer's Mice via Promoting Brain-Derived Neurotrophic Factor and Inhibiting Inflammation.
American journal of Alzheimer's disease and other dementias.
2022 Jan; 37(?):15333175221124949. doi:
10.1177/15333175221124949
. [PMID: 36113018] - Valentina Spigoni, Gloria Cinquegrani, Nicolas Thomas Iannozzi, Giulia Frigeri, Giulia Maggiolo, Marta Maggi, Vanessa Parello, Alessandra Dei Cas. Activation of G protein-coupled receptors by ketone bodies: Clinical implication of the ketogenic diet in metabolic disorders.
Frontiers in endocrinology.
2022; 13(?):972890. doi:
10.3389/fendo.2022.972890
. [PMID: 36339405] - Valeryia Mikalayeva, Monika Pankevičiūtė, Vaidotas Žvikas, V Arvydas Skeberdis, Sergio Bordel. Contribution of branched chain amino acids to energy production and mevalonate synthesis in cancer cells.
Biochemical and biophysical research communications.
2021 12; 585(?):61-67. doi:
10.1016/j.bbrc.2021.11.034
. [PMID: 34794035] - Ran Zhong, Renling Miao, Jiao Meng, Rimao Wu, Yong Zhang, Dahai Zhu. Acetoacetate promotes muscle cell proliferation via the miR-133b/SRF axis through the Mek-Erk-MEF2 pathway.
Acta biochimica et biophysica Sinica.
2021 Jul; 53(8):1009-1016. doi:
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Physiological research.
2020 11; 69(5):823-834. doi:
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2019 05; 109(5):1239-1250. doi:
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2019 04; 21(4):949-960. doi:
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2019 Jan; 66(1):107-114. doi:
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2018 05; 20(5):1321-1326. doi:
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Magnetic resonance in medicine.
2018 04; 79(4):1862-1869. doi:
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Journal of oleo science.
2018; 67(10):1235-1246. doi:
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Scientific reports.
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Cell chemical biology.
2017 Aug; 24(8):935-943.e7. doi:
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Analytical chemistry.
2017 05; 89(9):5066-5071. doi:
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Cell metabolism.
2017 02; 25(2):358-373. doi:
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Pharmacology.
2017; 100(3-4):194-200. doi:
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The journal of nutrition, health & aging.
2017; 21(6):681-685. doi:
10.1007/s12603-016-0786-y
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Journal of Alzheimer's disease : JAD.
2017; 56(4):1459-1468. doi:
10.3233/jad-161163
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Neurological research.
2017 Jan; 39(1):1-6. doi:
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Analytica chimica acta.
2016 Oct; 942(?):50-57. doi:
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International journal of environmental research and public health.
2016 08; 13(9):. doi:
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Free radical biology & medicine.
2016 06; 95(?):268-77. doi:
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PloS one.
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Annals of the American Thoracic Society.
2015 Jan; 12(1):46-56. doi:
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2014 Nov; 8(4):046008. doi:
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Neuropharmacology.
2014 Apr; 79(?):399-404. doi:
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2014 Mar; 97(3):1552-62. doi:
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Diabetes.
2013 Oct; 62(10):3618-26. doi:
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Diabetic medicine : a journal of the British Diabetic Association.
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Nutrition (Burbank, Los Angeles County, Calif.).
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Nutrition (Burbank, Los Angeles County, Calif.).
2012 Nov; 28(11-12):1122-6. doi:
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2012 May; 20(5):377-80. doi:
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Environmental health and preventive medicine.
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"
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