Ketoleucine (BioDeep_00000405339)
Main id: BioDeep_00000003211
natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019
代谢物信息卡片
化学式: C6H10O3 (130.063)
中文名称: 4-甲基-2-氧戊酸, 4-甲基-2-氧代戊酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)CC(=O)C(=O)O
InChI: InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
描述信息
A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.
4-Methyl-2-oxopentanoic acid (α-Ketoisocaproic acid), an abnormal metabolite, is both a neurotoxin and a metabotoxin.
同义名列表
数据库引用编号
26 个数据库交叉引用编号
- ChEBI: CHEBI:48430
- KEGG: C00233
- KEGGdrug: D82408
- PubChem: 70
- DrugBank: DB03229
- ChEMBL: CHEMBL445647
- CAS: 816-66-0
- MoNA: CCMSLIB00005720850
- MoNA: MoNA016732
- MoNA: FiehnHILIC002785
- MoNA: HMDB0000695_ms_ms_966
- MoNA: HMDB0000695_ms_ms_967
- MoNA: HMDB0000695_ms_ms_968
- MetaboLights: MTBLC48430
- ChEBI: CHEBI:17865
- PubChem: 3532
- KNApSAcK: C00019677
- PDB-CCD: COI
- 3DMET: B00066
- NIKKAJI: J39.557I
- RefMet: Ketoleucine
- medchemexpress: HY-W012722
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-591
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-509
- KNApSAcK: 17865
- LOTUS: LTS0087240
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
30 个相关的物种来源信息
- 3051 - Chlamydomonadaceae: LTS0087240
- 3052 - Chlamydomonas: LTS0087240
- 3055 - Chlamydomonas reinhardtii: 10.1111/TPJ.12747
- 3055 - Chlamydomonas reinhardtii: LTS0087240
- 3166 - Chlorophyceae: LTS0087240
- 3041 - Chlorophyta: LTS0087240
- 7711 - Chordata: LTS0087240
- 7227 - Drosophila melanogaster: 10.1038/S41467-019-11933-Z
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 2759 - Eukaryota: LTS0087240
- 9604 - Hominidae: LTS0087240
- 9605 - Homo: LTS0087240
- 9606 - Homo sapiens:
- 9606 - Homo sapiens: 10.1007/S11306-012-0464-Y
- 9606 - Homo sapiens: LTS0087240
- 3398 - Magnoliopsida: LTS0087240
- 40674 - Mammalia: LTS0087240
- 33208 - Metazoa: LTS0087240
- 4070 - Solanaceae: LTS0087240
- 4107 - Solanum: LTS0087240
- 4081 - Solanum lycopersicum: 10.1038/SDATA.2014.29
- 4081 - Solanum lycopersicum: LTS0087240
- 35493 - Streptophyta: LTS0087240
- 58023 - Tracheophyta: LTS0087240
- 33090 - Viridiplantae: LTS0087240
- 3602 - Vitaceae: LTS0087240
- 3603 - Vitis: LTS0087240
- 29760 - Vitis vinifera:
- 29760 - Vitis vinifera: 10.3389/FMICB.2017.00457
- 29760 - Vitis vinifera: LTS0087240
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
- Ângela Beatris Zemniaçak, Rafael Teixeira Ribeiro, Camila Vieira Pinheiro, Sâmela de Azevedo Cunha, Tailine Quevedo Tavares, Ediandra Tissot Castro, Guilhian Leipnitz, Moacir Wajner, Alexandre Umpierrez Amaral. In Vivo Intracerebral Administration of α-Ketoisocaproic Acid to Neonate Rats Disrupts Brain Redox Homeostasis and Promotes Neuronal Death, Glial Reactivity, and Myelination Injury.
Molecular neurobiology.
2023 Nov; ?(?):. doi:
10.1007/s12035-023-03718-9
. [PMID: 37910283] - Tae Jun Park, Seung Yeon Park, Hyun Jung Lee, A M Abd El-Aty, Ji Hoon Jeong, Tae Woo Jung. α-ketoisocaproic acid promotes ER stress through impairment of autophagy, thereby provoking lipid accumulation and insulin resistance in murine preadipocytes.
Biochemical and biophysical research communications.
2022 05; 603(?):109-115. doi:
10.1016/j.bbrc.2022.03.010
. [PMID: 35279461] - Xin Tang, Lulu Chang, Shujie Gu, Hao Zhang, Yong Q Chen, Haiqin Chen, Jianxin Zhao, Wei Chen. Role of beta-isopropylmalate dehydrogenase in lipid biosynthesis of the oleaginous fungus Mortierella alpina.
Fungal genetics and biology : FG & B.
2021 07; 152(?):103572. doi:
10.1016/j.fgb.2021.103572
. [PMID: 34015432] - Gabriella A M Ten Have, Lisa Jansen, Marieke G Schooneman, Marielle P K J Engelen, Nicolaas E P Deutz. Metabolic flux analysis of branched-chain amino and keto acids (BCAA, BCKA) and β-hydroxy β-methylbutyric acid across multiple organs in the pig.
American journal of physiology. Endocrinology and metabolism.
2021 03; 320(3):E629-E640. doi:
10.1152/ajpendo.00384.2020
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Metabolic brain disease.
2021 01; 36(1):185-192. doi:
10.1007/s11011-020-00626-y
. [PMID: 33034842] - Yinzhao Zhong, Bo Song, Changbing Zheng, Fengna Li, Xiangfeng Kong, Yehui Duan, Jinping Deng. α-Ketoisocaproate and β-hydroxy-β-methyl butyrate regulate fatty acid composition and lipid metabolism in skeletal muscle of growing pigs.
Journal of animal physiology and animal nutrition.
2019 May; 103(3):846-857. doi:
10.1111/jpn.13077
. [PMID: 30775808] - Yehui Duan, Lingyu Zhang, Fengna Li, Qiuping Guo, Cimin Long, Yulong Yin, Xiangfeng Kong, Mijun Peng, Wence Wang. β-Hydroxy-β-methylbutyrate modulates lipid metabolism in adipose tissues of growing pigs.
Food & function.
2018 Sep; 9(9):4836-4846. doi:
10.1039/c8fo00898a
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Scientific reports.
2018 07; 8(1):10056. doi:
10.1038/s41598-018-28477-9
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BioFactors (Oxford, England).
2018 May; 44(3):245-262. doi:
10.1002/biof.1415
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Canadian journal of physiology and pharmacology.
2018 Apr; 96(4):382-387. doi:
10.1139/cjpp-2017-0439
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Regulatory toxicology and pharmacology : RTP.
2017 Nov; 90(?):133-143. doi:
10.1016/j.yrtph.2017.09.004
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The Journal of nutrition.
2017 11; 147(11):2025-2030. doi:
10.3945/jn.117.250852
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Metabolic brain disease.
2017 10; 32(5):1507-1518. doi:
10.1007/s11011-017-0035-z
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American journal of physiology. Heart and circulatory physiology.
2017 Aug; 313(2):H432-H445. doi:
10.1152/ajpheart.00738.2016
. [PMID: 28646031] - Dillon K Walker, John J Thaden, Agata Wierzchowska-McNew, Marielle P K J Engelen, Nicolaas E P Deutz. Determination of β-hydroxy-β-methylbutyrate concentration and enrichment in human plasma using chemical ionization gas chromatography tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jan; 1040(?):233-238. doi:
10.1016/j.jchromb.2016.11.010
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Scientific reports.
2016 07; 6(?):28775. doi:
10.1038/srep28775
. [PMID: 27373929] - Sathyavageeswaran Shreeram, Subbarayan Ramesh, Jithesh K Puthan, Gayathri Balakrishnan, Ramachandran Subramanian, Murali Todime Reddy, Suzette L Pereira. Age associated decline in the conversion of leucine to β-Hydroxy-β-Methylbutyrate in rats.
Experimental gerontology.
2016 07; 80(?):6-11. doi:
10.1016/j.exger.2016.03.021
. [PMID: 27073170] - Miriam S W Wisniewski, Milena Carvalho-Silva, Lara M Gomes, Hugo G Zapelini, Patrícia F Schuck, Gustavo C Ferreira, Giselli Scaini, Emilio L Streck. Intracerebroventricular administration of α-ketoisocaproic acid decreases brain-derived neurotrophic factor and nerve growth factor levels in brain of young rats.
Metabolic brain disease.
2016 Apr; 31(2):377-83. doi:
10.1007/s11011-015-9768-8
. [PMID: 26586008] - Katsumi Shibata, Momoka Sakamoto. Urinary Branched-Chain 2-Oxo Acids as a Biomarker for Function of B-Group Vitamins in Humans.
Journal of nutritional science and vitaminology.
2016; 62(4):220-228. doi:
10.3177/jnsv.62.220
. [PMID: 27725406] - Katsumi Shibata, Chifumi Nakata, Tsutomu Fukuwatari. High-performance liquid chromatographic method for profiling 2-oxo acids in urine and its application in evaluating vitamin status in rats.
Bioscience, biotechnology, and biochemistry.
2016; 80(2):304-12. doi:
10.1080/09168451.2015.1083395
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PloS one.
2016; 11(10):e0164877. doi:
10.1371/journal.pone.0164877
. [PMID: 27741291] - Andrew D James, Waseema Patel, Zohra Butt, Magretta Adiamah, Raga Dakhel, Ayse Latif, Carolina Uggenti, Eileithyia Swanton, Hiromi Imamura, Ajith K Siriwardena, Jason I E Bruce. The Plasma Membrane Calcium Pump in Pancreatic Cancer Cells Exhibiting the Warburg Effect Relies on Glycolytic ATP.
The Journal of biological chemistry.
2015 Oct; 290(41):24760-71. doi:
10.1074/jbc.m115.668707
. [PMID: 26294767] - Anthony J Lee, David W A Beno, Xiaolin Zhang, Robin Shapiro, Mark Mason, Tanita Mason-Bright, Bruce Surber, Neilé K Edens. A (14)C-leucine absorption, distribution, metabolism and excretion (ADME) study in adult Sprague-Dawley rat reveals β-hydroxy-β-methylbutyrate as a metabolite.
Amino acids.
2015 May; 47(5):917-24. doi:
10.1007/s00726-015-1920-6
. [PMID: 25618754] - Xiaoya Huang, Yuan Zhong, Zhongping Huang, Chen Jin, Lili Wang, Zaifa Pan. [Simultaneous determination of five active components of compound α-ketoacid tablet in human urine by ion-pair reversed-phase high performance liquid chromatography].
Se pu = Chinese journal of chromatography.
2015 Feb; 33(2):169-73. doi:
10.3724/sp.j.1123.2014.10024
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Biochemical and biophysical research communications.
2015 Jan; 456(2):610-4. doi:
10.1016/j.bbrc.2014.12.003
. [PMID: 25499815] - Hester Vlaardingerbroek, Jorine A Roelants, Denise Rook, Kristien Dorst, Henk Schierbeek, Andras Vermes, Marijn J Vermeulen, Johannes B van Goudoever, Chris H P van den Akker. Adaptive regulation of amino acid metabolism on early parenteral lipid and high-dose amino acid administration in VLBW infants - a randomized, controlled trial.
Clinical nutrition (Edinburgh, Scotland).
2014 Dec; 33(6):982-90. doi:
10.1016/j.clnu.2014.01.002
. [PMID: 24461877] - M Sakko, C Moore, L Novak-Frazer, V Rautemaa, T Sorsa, P Hietala, A Järvinen, P Bowyer, L Tjäderhane, R Rautemaa. 2-hydroxyisocaproic acid is fungicidal for Candida and Aspergillus species.
Mycoses.
2014 Apr; 57(4):214-21. doi:
10.1111/myc.12145
. [PMID: 24125484] - Hiroyuki Hachiya, Yoshikazu Miura, Ken-Ichi Inoue, Kyung Hwa Park, Masayoshi Takeuchi, Keiichi Kubota. Advanced glycation end products impair glucose-induced insulin secretion from rat pancreatic β-cells.
Journal of hepato-biliary-pancreatic sciences.
2014 Feb; 21(2):134-41. doi:
10.1002/jhbp.12
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The American journal of clinical nutrition.
2012 Oct; 96(4):759-67. doi:
10.3945/ajcn.111.024471
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Toxicology.
2012 Sep; 299(2-3):165-71. doi:
10.1016/j.tox.2012.05.021
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Journal of proteome research.
2012 Sep; 11(9):4425-35. doi:
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PloS one.
2012; 7(7):e40600. doi:
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PloS one.
2012; 7(1):e28761. doi:
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Methods in molecular biology (Clifton, N.J.).
2012; 889(?):425-36. doi:
10.1007/978-1-61779-867-2_26
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Nutrition & metabolism.
2011 Dec; 8(?):91. doi:
10.1186/1743-7075-8-91
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PLoS computational biology.
2011 Oct; 7(10):e1002257. doi:
10.1371/journal.pcbi.1002257
. [PMID: 22046124] - Jia V Li, Jasmina Saric, Yulan Wang, Jennifer Keiser, Jürg Utzinger, Elaine Holmes. Chemometric analysis of biofluids from mice experimentally infected with Schistosoma mansoni.
Parasites & vectors.
2011 Sep; 4(?):179. doi:
10.1186/1756-3305-4-179
. [PMID: 21929782] - Lei Gong, Nelly Aranibar, Yong-Hae Han, Youcai Zhang, Lloyd Lecureux, Vasanthi Bhaskaran, Purnima Khandelwal, Curtis D Klaassen, Lois D Lehman-McKeeman. Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles.
Toxicological sciences : an official journal of the Society of Toxicology.
2011 Aug; 122(2):587-97. doi:
10.1093/toxsci/kfr114
. [PMID: 21561886] - Jia V Li, Jasmina Saric, Yulan Wang, Jürg Utzinger, Elaine Holmes, Oliver Balmer. Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections.
The American journal of tropical medicine and hygiene.
2011 Jan; 84(1):91-8. doi:
10.4269/ajtmh.2011.10-0402
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mBio.
2011; 2(2):e00271-10. doi:
10.1128/mbio.00271-10
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PloS one.
2010 Dec; 5(12):e15234. doi:
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Journal of proteome research.
2010 Dec; 9(12):6405-16. doi:
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Journal of dairy science.
2010 Sep; 93(9):4165-79. doi:
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. [PMID: 20723691] - Junfang Wu, Wenxin Xu, Zhenping Ming, Huifen Dong, Huiru Tang, Yulan Wang. Metabolic changes reveal the development of schistosomiasis in mice.
PLoS neglected tropical diseases.
2010 Aug; 4(8):. doi:
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. [PMID: 20824219] - Jeffery Escobar, Jason W Frank, Agus Suryawan, Hanh V Nguyen, Cynthia G Van Horn, Susan M Hutson, Teresa A Davis. Leucine and alpha-ketoisocaproic acid, but not norleucine, stimulate skeletal muscle protein synthesis in neonatal pigs.
The Journal of nutrition.
2010 Aug; 140(8):1418-24. doi:
10.3945/jn.110.123042
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Journal of lipid research.
2010 Aug; 51(8):2171-80. doi:
10.1194/jlr.m000802
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Molecular and cellular endocrinology.
2010 Jul; 323(2):246-55. doi:
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Plant physiology.
2010 Jul; 153(3):925-36. doi:
10.1104/pp.110.154922
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Journal of proteome research.
2010 May; 9(5):2255-64. doi:
10.1021/pr901019z
. [PMID: 20092362] - Anthony Schilmiller, Feng Shi, Jeongwoon Kim, Amanda L Charbonneau, Daniel Holmes, A Daniel Jones, Robert L Last. Mass spectrometry screening reveals widespread diversity in trichome specialized metabolites of tomato chromosomal substitution lines.
The Plant journal : for cell and molecular biology.
2010 May; 62(3):391-403. doi:
10.1111/j.1365-313x.2010.04154.x
. [PMID: 20113441] - Alexandre Umpierrez Amaral, Guilhian Leipnitz, Carolina Gonçalves Fernandes, Bianca Seminotti, Patrícia Fernanda Schuck, Moacir Wajner. Alpha-ketoisocaproic acid and leucine provoke mitochondrial bioenergetic dysfunction in rat brain.
Brain research.
2010 Apr; 1324(?):75-84. doi:
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