Acetoin (BioDeep_00000004235)

human metabolite blood metabolite

代谢物信息卡片

1-Hydroxyethyl methyl ketone

化学式: C4H8O2 (88.0524268)
中文名称: 乙偶姻, 乙酰甲基甲醇
谱图信息: 最多检出来源 Homo sapiens(blood) 79.79%

分子结构信息

SMILES: CC(=O)C(C)O
InChI: InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3

描述信息

Acetoin, also known as dimethylketol or 2,3-butanolone, belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thus, acetoin is considered to be an oxygenated hydrocarbon lipid molecule. Acetoin is used as an external energy store by a number of fermentive bacteria. Acetoin, along with diacetyl, is one of the compounds giving butter its characteristic flavor. Acetoin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Acetoin is used as a food flavoring (in baked goods) and a fragrance. Acetoin is a sweet, buttery, and creamy tasting compound. Outside of the human body, Acetoin has been detected, but not quantified in several different foods, such as cocoa and cocoa products, evergreen blackberries, orange bell peppers, tortilla chips, and pomes. This could make acetoin a potential biomarker for the consumption of these foods. Constituent of beer, wine, fresh or cooked apple, fresh or cooked leak, corn, honey, cocoa, butter, cheeses, roasted coffee and other foodstuffs. Acetoin, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and ulcerative colitis; acetoin has also been linked to the inborn metabolic disorder celiac disease. Acetoin is a colorless or pale yellow to green yellow liquid with a pleasant, buttery odor. It can be found in apples, butter, yogurt, asparagus, black currants, blackberry, wheat, broccoli, brussels sprouts, cantaloupe.
Constituent of beer, wine, fresh or cooked apple, fresh or cooked leak, corn, honey, cocoa, butter, cheeses, roasted coffee and other foodstuffs. Flavouring ingredient. [DFC]

同义名列表

27 个代谢物同义名

1-Hydroxyethyl methyl ketone; gamma-Hydroxy-beta-oxobutane; (R)-3-Hydroxybutan-2-one; (R)-3-Hydroxy-2-butanone; Acetyl methyl carbinol; Γ-hydroxy-β-oxobutane; g-Hydroxy-b-oxobutane; 3-Hydroxyl-2-butanone; 2-Hydroxy-3-oxobutane; 3-hydroxy-2-Butanone; 3-Hydroxybutan-2-one; 2-Hydroxy-3-butanone; Acetylmethylcarbinol; (R)-Dimethylketol; 2-Butanol-3-one; beta-Oxobutane; 3H-2b Butanone; 2,3-Butanolone; Dimethylketol; (R)-2-Acetoin; (S)-2-Acetoin; b-Oxobutane; (R)-Acetoin; 2-Acetoin; Acetoine; acetoin; Acetoin

数据库引用编号

19 个数据库交叉引用编号

ChEBI: CHEBI:15688
KEGG: C00466
KEGGdrug: D93492
PubChem: 179
HMDB: HMDB0003243
ChEMBL: CHEMBL3561873
Wikipedia: Acetoin
MeSH: Acetoin
MetaCyc: ACETOIN
KNApSAcK: C00050424
foodb: FDB011799
chemspider: 21105851
CAS: 51555-24-9
CAS: 513-86-0
PMhub: MS000016129
PubChem: 3750
LipidMAPS: LMFA12000020
NIKKAJI: J2.623I
RefMet: Acetoin

分类词条

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)

67 个相关的物种来源信息

151847 Malpighia emarginata: 10.1016/S0308-8146(00)00152-7
71611 Malpighia glabra: 10.1016/S0308-8146(00)00152-7
4681 Allium ampeloprasum: 10.1080/10412905.1991.9697935
329675 Daphne odora: 10.1271/BBB1961.47.483
2715869 Daphne papyracea: 10.1271/BBB1961.47.483
29760 Vitis vinifera: 10.3389/FMICB.2017.00457
62097 Plumeria rubra: 10.1002/FFJ.2730070108
3760 Prunus persica: 10.1021/JF00004A032
36596 Prunus armeniaca: 10.1021/JF00004A032
3758 Prunus domestica: 10.1021/JF00004A032
263 Francisella tularensis: 10.1038/S41598-020-66136-0
1392 Bacillus anthracis: 10.1038/S41598-020-66136-0
13443 Coffea arabica:
4442 Camellia sinensis: 10.1021/JF00034A031
49827 Glycyrrhiza glabra: 10.1021/JF60214A042
3641 Theobroma cacao: 10.1021/JF60160A011
4232 Helianthus annuus: 10.1021/JF00123A021
4072 Capsicum annuum: 10.1006/JFCA.1997.0535
45385 Aloe arborescens: 10.1021/JF990116I
151069 Litchi chinensis: 10.1021/JF60230A021
2849048 Lucensosergia lucens: 10.1080/00021369.1984.10866348
589641 Sergia lucens: 10.1080/00021369.1984.10866348
57577 Trifolium pratense: 10.1021/JF00122A019
1886 Streptomyces albidoflavus: 10.1007/S12223-008-0049-3
1902 Streptomyces coelicolor: 10.1007/S12223-008-0049-3
68270 Streptomyces spectabilis: 10.1007/S12223-008-0049-3
1961 Streptomyces virginiae: 10.1007/S12223-008-0049-3
33903 Streptomyces avermitilis: 10.1007/S12223-008-0049-3
68174 Streptomyces anthocyanicus: 10.1007/S12223-008-0049-3
1911 Streptomyces griseus: 10.1007/S12223-008-0049-3
1927 Streptomyces rimosus: 10.1007/S12223-008-0049-3
1894 Kitasatospora aureofaciens: 10.1007/S12223-008-0049-3
1916 Streptomyces lividans: 10.1007/S12223-008-0049-3
151847 Malpighia emarginata: 10.1016/S0308-8146(00)00152-7
71611 Malpighia glabra: 10.1016/S0308-8146(00)00152-7
4681 Allium ampeloprasum: 10.1080/10412905.1991.9697935
329675 Daphne odora: 10.1271/BBB1961.47.483
2715869 Daphne papyracea: 10.1271/BBB1961.47.483
29760 Vitis vinifera: 10.3389/FMICB.2017.00457
62097 Plumeria rubra: 10.1002/FFJ.2730070108
3760 Prunus persica: 10.1021/JF00004A032
36596 Prunus armeniaca: 10.1021/JF00004A032
3758 Prunus domestica: 10.1021/JF00004A032
263 Francisella tularensis: 10.1038/S41598-020-66136-0
1392 Bacillus anthracis: 10.1038/S41598-020-66136-0
13443 Coffea arabica:
4442 Camellia sinensis: 10.1021/JF00034A031
49827 Glycyrrhiza glabra: 10.1021/JF60214A042
3641 Theobroma cacao: 10.1021/JF60160A011
4232 Helianthus annuus: 10.1021/JF00123A021
4072 Capsicum annuum: 10.1006/JFCA.1997.0535
45385 Aloe arborescens: 10.1021/JF990116I
151069 Litchi chinensis: 10.1021/JF60230A021
2849048 Lucensosergia lucens: 10.1080/00021369.1984.10866348
589641 Sergia lucens: 10.1080/00021369.1984.10866348
57577 Trifolium pratense: 10.1021/JF00122A019
1886 Streptomyces albidoflavus: 10.1007/S12223-008-0049-3
1902 Streptomyces coelicolor: 10.1007/S12223-008-0049-3
68270 Streptomyces spectabilis: 10.1007/S12223-008-0049-3
1961 Streptomyces virginiae: 10.1007/S12223-008-0049-3
33903 Streptomyces avermitilis: 10.1007/S12223-008-0049-3
68174 Streptomyces anthocyanicus: 10.1007/S12223-008-0049-3
1911 Streptomyces griseus: 10.1007/S12223-008-0049-3
1927 Streptomyces rimosus: 10.1007/S12223-008-0049-3
1894 Kitasatospora aureofaciens: 10.1007/S12223-008-0049-3
1916 Streptomyces lividans: 10.1007/S12223-008-0049-3
9606 Homo sapiens: -

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

Tania N N Tanwee, Gina L Lipscomb, Jason L Vailionis, Ke Zhang, Ryan G Bing, Hailey C O'Quinn, Farris L Poole, Ying Zhang, Robert M Kelly, Michael W W Adams. Metabolic engineering of Caldicellulosiruptor bescii for 2,3-butanediol production from unpretreated lignocellulosic biomass and metabolic strategies for improving yields and titers. Applied and environmental microbiology. 2024 Jan; 90(1):e0195123. doi: 10.1128/aem.01951-23. [PMID: 38131671]
Moldir Koilybayeva, Zhanserik Shynykul, Gulbaram Ustenova, Krzysztof Waleron, Joanna Jońca, Kamilya Mustafina, Akerke Amirkhanova, Yekaterina Koloskova, Raushan Bayaliyeva, Tamila Akhayeva, Mereke Alimzhanova, Aknur Turgumbayeva, Gulden Kurmangaliyeva, Aigerim Kantureyeva, Dinara Batyrbayeva, Zhazira Alibayeva. Gas Chromatography-Mass Spectrometry Profiling of Volatile Metabolites Produced by Some Bacillus spp. and Evaluation of Their Antibacterial and Antibiotic Activities. Molecules (Basel, Switzerland). 2023 Nov; 28(22):. doi: 10.3390/molecules28227556. [PMID: 38005278]
Ko Mochizuki, Tomoko Okamoto, Kai-Hsiu Chen, Chun-Neng Wang, Matthew Evans, Andrea T Kramer, Atsushi Kawakita. Adaptation to pollination by fungus gnats underlies the evolution of pollination syndrome in the genus Euonymus. Annals of botany. 2023 Aug; ?(?):. doi: 10.1093/aob/mcad081. [PMID: 37610846]
Zhenzhao Li, Minh Ha, Damian Frank, Melindee Hastie, Robyn D Warner. Muscle fibre type composition influences the formation of odour-active volatiles in beef. Food research international (Ottawa, Ont.). 2023 03; 165(?):112468. doi: 10.1016/j.foodres.2023.112468. [PMID: 36869481]
Qian Luo, Nana Ding, Yunfeng Liu, Hailing Zhang, Yu Fang, Lianghong Yin. Metabolic Engineering of Microorganisms to Produce Pyruvate and Derived Compounds. Molecules (Basel, Switzerland). 2023 Feb; 28(3):. doi: 10.3390/molecules28031418. [PMID: 36771084]
Dan Qiu, Rubi Duan, Yueqi Wang, Yanfu He, Chuan Li, Xuanri Shen, Yongcheng Li. Effects of different drying temperatures on the profile and sources of flavor in semi-dried golden pompano (Trachinotus ovatus). Food chemistry. 2023 Feb; 401(?):134112. doi: 10.1016/j.foodchem.2022.134112. [PMID: 36099819]
Suyoung Song, Eun Kyeong Jeon, Cher-Won Hwang. Characteristic Analysis of Soil-Isolated Bacillus velezensis HY-3479 and Its Antifungal Activity Against Phytopathogens. Current microbiology. 2022 Oct; 79(12):357. doi: 10.1007/s00284-022-03060-8. [PMID: 36251101]
Jana Štefániková, Július Árvay, Simona Kunová, Przemysław Łukasz Kowalczewski, Miroslava Kačániová. Aroma profile and lactic acid bacteria characteristic of traditional Slovak cheese 'May bryndza'. Food science and technology international = Ciencia y tecnologia de los alimentos internacional. 2022 Oct; 28(7):580-591. doi: 10.1177/10820132211039916. [PMID: 34515545]
Bénédicte Cesselin, Céline Henry, Alexandra Gruss, Karine Gloux, Philippe Gaudu. Mechanisms of Acetoin Toxicity and Adaptive Responses in an Acetoin-Producing Species, Lactococcus lactis. Applied and environmental microbiology. 2021 11; 87(24):e0107921. doi: 10.1128/aem.01079-21. [PMID: 34613757]
Yucong Li, Jiahui Shao, Yuanming Xie, Letian Jia, Yansong Fu, Zhihui Xu, Nan Zhang, Haichao Feng, Weibing Xun, Yunpeng Liu, Qirong Shen, Wei Xuan, Ruifu Zhang. Volatile compounds from beneficial rhizobacteria Bacillus spp. promote periodic lateral root development in Arabidopsis. Plant, cell & environment. 2021 05; 44(5):1663-1678. doi: 10.1111/pce.14021. [PMID: 33548150]
Kai Peng, Dan Guo, Qianqian Lou, Xiaoyun Lu, Jian Cheng, Jing Qiao, Lina Lu, Tao Cai, Yuwan Liu, Huifeng Jiang. Synthesis of Ligustrazine from Acetaldehyde by a Combined Biological-Chemical Approach. ACS synthetic biology. 2020 11; 9(11):2902-2908. doi: 10.1021/acssynbio.0c00113. [PMID: 33156612]
Lidong Liu, Xiuyun Zhao, Yong Huang, Luxin Ke, Rui Wang, Gaofu Qi. Protecting tobacco plants from O3 injury by Bacillus velezensis with production of acetoin. Physiologia plantarum. 2020 Oct; 170(2):158-171. doi: 10.1111/ppl.13120. [PMID: 32386333]
Qi Peng, Xin Zhao, Jilong Wen, Minzhong Huang, Jie Zhang, Fuping Song. Transcription in the acetoin catabolic pathway is regulated by AcoR and CcpA in Bacillus thuringiensis. Microbiological research. 2020 May; 235(?):126438. doi: 10.1016/j.micres.2020.126438. [PMID: 32088504]
Annalaura Lopez, Mauro Vasconi, Federica Bellagamba, Tiziana Mentasti Mario Pazzaglia, Vittorio Maria Moretti. Volatile Organic Compounds Profile in White Sturgeon (Acipenser transmontanus) Caviar at Different Stages of Ripening by Multiple Headspace Solid Phase Microextraction. Molecules (Basel, Switzerland). 2020 Feb; 25(5):. doi: 10.3390/molecules25051074. [PMID: 32121013]
Rabiatuladawiyah Ruzmi, Muhammad Saiful Ahmad-Hamdani, Norida Mazlan. Ser-653-Asn substitution in the acetohydroxyacid synthase gene confers resistance in weedy rice to imidazolinone herbicides in Malaysia. PloS one. 2020; 15(9):e0227397. doi: 10.1371/journal.pone.0227397. [PMID: 32925921]
Ge Peng, Xiuyun Zhao, Yazhou Li, Rui Wang, Yong Huang, Gaofu Qi. Engineering Bacillus velezensis with high production of acetoin primes strong induced systemic resistance in Arabidopsis thaliana. Microbiological research. 2019 Oct; 227(?):126297. doi: 10.1016/j.micres.2019.126297. [PMID: 31421711]
Liming Wu, Xi Li, Liumin Ma, Rainer Borriss, Zhen Wu, Xuewen Gao. Acetoin and 2,3-butanediol from Bacillus amyloliquefaciens induce stomatal closure in Arabidopsis thaliana and Nicotiana benthamiana. Journal of experimental botany. 2018 11; 69(22):5625-5635. doi: 10.1093/jxb/ery326. [PMID: 30295868]
Shihui Wang, Qiuling Luo, Jia Liu, Liming Liu, Xiulai Chen. [Mutation and fermentation optimization of Bacillus amyloliquefaciens for acetoin production]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2018 May; 34(5):803-811. doi: 10.13345/j.cjb.170446. [PMID: 29893088]
M Rath, T R Mitchell, S E Gold. Volatiles produced by Bacillus mojavensis RRC101 act as plant growth modulators and are strongly culture-dependent. Microbiological research. 2018 Mar; 208(?):76-84. doi: 10.1016/j.micres.2017.12.014. [PMID: 29551214]
Paola Fincheira, Andrés Quiroz. Microbial volatiles as plant growth inducers. Microbiological research. 2018 Mar; 208(?):63-75. doi: 10.1016/j.micres.2018.01.002. [PMID: 29551213]
Frédéric Cosnier, Stéphane Grossmann, Hervé Nunge, Céline Brochard, Samuel Muller, Anne-Marie Lambert-Xolin, Sylvie Sebillaud, Benoît Rieger, Aurélie Thomas, Marie-Josèphe Décret, Manuella Burgart, Laurent Gaté, Benoît Cossec, Pierre Campo. Metabolism of inhaled methylethylketone in rats. Drug and chemical toxicology. 2018 Jan; 41(1):42-50. doi: 10.1080/01480545.2017.1289220. [PMID: 28633598]
Valentina Lazazzara, Michele Perazzolli, Ilaria Pertot, Franco Biasioli, Gerardo Puopolo, Luca Cappellin. Growth media affect the volatilome and antimicrobial activity against Phytophthora infestans in four Lysobacter type strains. Microbiological research. 2017 Aug; 201(?):52-62. doi: 10.1016/j.micres.2017.04.015. [PMID: 28602402]
Yu-Ichi Yamada, Gen Yamada, Mitsuo Otsuka, Hirotaka Nishikiori, Kimiyuki Ikeda, Yasuaki Umeda, Hirofumi Ohnishi, Koji Kuronuma, Hirofumi Chiba, Jörg Ingo Baumbach, Hiroki Takahashi. Volatile Organic Compounds in Exhaled Breath of Idiopathic Pulmonary Fibrosis for Discrimination from Healthy Subjects. Lung. 2017 04; 195(2):247-254. doi: 10.1007/s00408-017-9979-3. [PMID: 28247041]
Ramya Krishnan, Rahul R Menon, Likhitha, Hans-Jürgen Busse, Naoto Tanaka, Srinivasan Krishnamurthi, N Rameshkumar. Novosphingobium pokkalii sp nov, a novel rhizosphere-associated bacterium with plant beneficial properties isolated from saline-tolerant pokkali rice. Research in microbiology. 2017 Feb; 168(2):113-121. doi: 10.1016/j.resmic.2016.09.001. [PMID: 27639667]
Abdur Rahim Khan, Gun-Seok Park, Sajjad Asaf, Sung-Jun Hong, Byung Kwon Jung, Jae-Ho Shin. Complete genome analysis of Serratia marcescens RSC-14: A plant growth-promoting bacterium that alleviates cadmium stress in host plants. PloS one. 2017; 12(2):e0171534. doi: 10.1371/journal.pone.0171534. [PMID: 28187139]
Shujing Sun, Haiyang Zhang, Shuyi Lu, Chunfen Lai, Huijun Liu, Hu Zhu. The metabolic flux regulation of Klebsiella pneumoniae based on quorum sensing system. Scientific reports. 2016 12; 6(?):38725. doi: 10.1038/srep38725. [PMID: 27924940]
Paola Fincheira, Herbert Venthur, Ana Mutis, Maribel Parada, Andrés Quiroz. Growth promotion of Lactuca sativa in response to volatile organic compounds emitted from diverse bacterial species. Microbiological research. 2016 Dec; 193(?):39-47. doi: 10.1016/j.micres.2016.09.008. [PMID: 27825485]
Joon-hui Chung, Geun Cheol Song, Choong-Min Ryu. Sweet scents from good bacteria: Case studies on bacterial volatile compounds for plant growth and immunity. Plant molecular biology. 2016 Apr; 90(6):677-87. doi: 10.1007/s11103-015-0344-8. [PMID: 26177913]
Emin Yılmaz, Mustafa Öğütcü, Yonca Karagül Yüceer. Physical Properties, Volatiles Compositions and Sensory Descriptions of the Aromatized Hazelnut Oil-Wax Organogels. Journal of food science. 2015 Sep; 80(9):S2035-44. doi: 10.1111/1750-3841.12992. [PMID: 26259923]
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Bruce A Kimball, Kunio Yamazaki, Dennis Kohler, Richard A Bowen, Jack P Muth, Maryanne Opiekun, Gary K Beauchamp. Avian influenza infection alters fecal odor in mallards. PloS one. 2013; 8(10):e75411. doi: 10.1371/journal.pone.0075411. [PMID: 24146753]
Alistair Paterson, Angzzas Kassim, Susan McCallum, Mary Woodhead, Kay Smith, Dzeti Zait, Julie Graham. Environmental and seasonal influences on red raspberry flavour volatiles and identification of quantitative trait loci (QTL) and candidate genes. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2013 Jan; 126(1):33-48. doi: 10.1007/s00122-012-1957-9. [PMID: 22890807]
Andre F Cruz, Chantal Hamel, Chao Yang, Tomoko Matsubara, Yantai Gan, Asheesh K Singh, Kousaku Kuwada, Takaaki Ishii. Phytochemicals to suppress Fusarium head blight in wheat-chickpea rotation. Phytochemistry. 2012 Jun; 78(?):72-80. doi: 10.1016/j.phytochem.2012.03.003. [PMID: 22520499]
Lavanya Babujee, Jennifer Apodaca, Venkatesh Balakrishnan, Paul Liss, Patricia J Kiley, Amy O Charkowski, Jeremy D Glasner, Nicole T Perna. Evolution of the metabolic and regulatory networks associated with oxygen availability in two phytopathogenic enterobacteria. BMC genomics. 2012 Mar; 13(?):110. doi: 10.1186/1471-2164-13-110. [PMID: 22439737]
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