Isobutanol (BioDeep_00000004229)

 

Secondary id: BioDeep_00000629760

human metabolite Endogenous


代谢物信息卡片


Isobutyl alcohol, titanium (+4) salt

化学式: C4H10O (74.0732)
中文名称: 乙醇中异丁醇, 异丁醇
谱图信息: 最多检出来源 Homo sapiens(feces) 76.49%

分子结构信息

SMILES: CC(C)CO
InChI: InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3

描述信息

Isobutanol is an aliphatic alcohol. Isobutanol is a colorless, flammable, organic compound with a characteristic smell. Isobutanol is widely used in industry, as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis. Isobutanol is a flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis. Isobutanol is occasionally found as a volatile component of urine and arises from gut microbial metabolism. Isobutanol is used as one of the markers to measure occupational exposure to a mixture of solvents. Aliphatic alcohols levels increase in both diabetes mellitus and insulin-dependent diabetes patients. (PMID:5556886, 2477620, 9143482, 7627316, 2288731). Isobutanol is a microbial metabolite found in Clostridium, Cupriavidus, Escherichia, Geobacillus, Saccharomyces and Synechococcus (PMID:19946322).
Present in fusel oil, wines and spirits and produced by fermentation of carbohydrates. It is used in the manuf. of flavouring essences. 2-Methyl-1-propanol is found in many foods, some of which are white mustard, chinese cabbage, pummelo, and parsley.

同义名列表

28 个代谢物同义名

Isobutyl alcohol, titanium (+4) salt; Isobutyl alcohol, aluminum salt; Isobutyl alcohol, sodium salt; 2-Methyl-1-propanyl alcohol; 1-Hydroxymethylpropane; 2-Methylpropyl alcohol; Alcool isobutylique; 2-methyl-1-propanol; Methyl-2 propanol-1; 2-Methylpropan-1-ol; 2-Methylpropanol-1; Isopropyl carbitol; 2-Methyl propanol; Isopropylcarbinol; Iso-butyl alcohol; 2-Methylpropanol; 2-MethylpropanoI; Isobutyl alcohol; Isobutylalkohol; I-butyl alcohol; 1-isobutanol; Isobutanol; Iso-C4H9OH; I-butanol; FOH 4:0; IBA; Isobutyl alcohol; Isobutanol



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(0)

代谢反应

13 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(12)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • Valine Degradation: L-Valine + Oxoglutaric acid ⟶ -Ketoisovaleric acid + L-Glutamic acid

PharmGKB(0)

23 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 5 EIF2B1, G6PD, LDHA, PC, PMP2
Peripheral membrane protein 2 G6PD, HSD17B6
Nucleus 6 ATF1, CS, LDHA, PDC, PMP2, PNKD
cytosol 11 ADH7, AKR1A1, EIF2B1, G6PD, LDHA, LIPE, NADK, PC, PDC, PMP2, XYLB
nucleoplasm 1 ATF1
RNA polymerase II transcription regulator complex 1 ATF1
Cell membrane 2 LIPE, PTAFR
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 PTAFR
Synapse 1 AKR1A1
Golgi apparatus 1 ATRN
Cytoplasm, cytosol 5 AKR1A1, EIF2B1, G6PD, LIPE, PDC
plasma membrane 4 ADH7, ATRN, EIF2B1, PTAFR
Membrane 7 CS, EIF2B1, G6PD, LDHA, LIPE, PNKD, PTAFR
apical plasma membrane 1 AKR1A1
caveola 1 LIPE
extracellular exosome 6 AKR1A1, ATRN, CS, G6PD, LDHA, PMP2
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 2 AKR1A1, ATRN
mitochondrion 4 CS, LDHA, PC, PNKD
intracellular membrane-bounded organelle 2 G6PD, HSD17B6
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 1 ATRN
extracellular region 1 PROK2
cytoplasmic side of plasma membrane 1 G6PD
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 2 CS, PC
mitochondrial matrix 2 CS, PC
centriolar satellite 1 G6PD
photoreceptor inner segment 1 PDC
photoreceptor outer segment 1 PDC
Apical cell membrane 1 AKR1A1
chromatin 1 ATF1
Cell projection, cilium, photoreceptor outer segment 1 PDC
[Isoform 3]: Secreted 1 ATRN
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
tertiary granule membrane 1 PTAFR
myelin sheath 1 PMP2
secretory granule membrane 1 PTAFR
[Isoform 2]: Nucleus 1 PDC
[Isoform 1]: Cell membrane 1 ATRN
presynaptic cytosol 1 PNKD
oxidoreductase complex 1 LDHA
ATF4-CREB1 transcription factor complex 1 ATF1
ATF1-ATF4 transcription factor complex 1 ATF1
eukaryotic translation initiation factor 2B complex 1 EIF2B1


文献列表

  • A Di Francesco, J Zajc, N Gunde-Cimerman, E Aprea, F Gasperi, N Placì, F Caruso, E Baraldi. Bioactivity of volatile organic compounds by Aureobasidium species against gray mold of tomato and table grape. World journal of microbiology & biotechnology. 2020 Oct; 36(11):171. doi: 10.1007/s11274-020-02947-7. [PMID: 33067644]
  • Yang Liu, Indro Neil Ghosh, Julia Martien, Yaoping Zhang, Daniel Amador-Noguez, Robert Landick. Regulated redirection of central carbon flux enhances anaerobic production of bioproducts in Zymomonas mobilis. Metabolic engineering. 2020 09; 61(?):261-274. doi: 10.1016/j.ymben.2020.06.005. [PMID: 32590077]
  • Kouichi Kuroda, Sarah K Hammer, Yukio Watanabe, José Montaño López, Gerald R Fink, Gregory Stephanopoulos, Mitsuyoshi Ueda, José L Avalos. Critical Roles of the Pentose Phosphate Pathway and GLN3 in Isobutanol-Specific Tolerance in Yeast. Cell systems. 2019 12; 9(6):534-547.e5. doi: 10.1016/j.cels.2019.10.006. [PMID: 31734159]
  • Carl E Creutz. Expression of Metazoan Annexins in Yeast Provides Protection Against Deleterious Effects of the Biofuel Isobutanol. Scientific reports. 2019 12; 9(1):18603. doi: 10.1038/s41598-019-55169-9. [PMID: 31819124]
  • Liang Tian, Nicholas D Cervenka, Aidan M Low, Daniel G Olson, Lee R Lynd. A mutation in the AdhE alcohol dehydrogenase of Clostridium thermocellum increases tolerance to several primary alcohols, including isobutanol, n-butanol and ethanol. Scientific reports. 2019 02; 9(1):1736. doi: 10.1038/s41598-018-37979-5. [PMID: 30741948]
  • Jun Li, Michele R Richards, Elena N Kitova, John S Klassen. Delivering Transmembrane Peptide Complexes to the Gas Phase Using Nanodiscs and Electrospray Ionization. Journal of the American Society for Mass Spectrometry. 2017 10; 28(10):2054-2065. doi: 10.1007/s13361-017-1735-7. [PMID: 28681358]
  • Shuchi H Desai, Christine A Rabinovitch-Deere, Zhiliang Fan, Shota Atsumi. Isobutanol production from cellobionic acid in Escherichia coli. Microbial cell factories. 2015 Apr; 14(?):52. doi: 10.1186/s12934-015-0232-6. [PMID: 25889729]
  • Haifeng Su, Juan Jiang, Qiuli Lu, Zhao Zhao, Tian Xie, Hai Zhao, Maolin Wang. Engineering Corynebacterium crenatum to produce higher alcohols for biofuel using hydrolysates of duckweed (Landoltia punctata) as feedstock. Microbial cell factories. 2015 Feb; 14(?):16. doi: 10.1186/s12934-015-0199-3. [PMID: 25889648]
  • Nasir Ali, Dawood Ahmad, Jehan Bakht. Antimicrobial activity of different solvent extracted samples from the flowers of medicinally important Plumeria obstusa. Pakistan journal of pharmaceutical sciences. 2015 Jan; 28(1):195-200. doi: . [PMID: 25553696]
  • Indumathy Jayamani, Alison M Cupples. Effect of isobutanol on toluene biodegradation in nitrate amended, sulfate amended and methanogenic enrichment microcosms. Biodegradation. 2013 Sep; 24(5):657-63. doi: 10.1007/s10532-012-9613-2. [PMID: 23224907]
  • Bharathiraja Balasubramaniam, Ayyappasamy Sudalaiyadum Perumal, Jayamuthunagai Jayaraman, Jayakumar Mani, Praveenkumar Ramanujam. Comparative analysis for the production of fatty acid alkyl esterase using whole cell biocatalyst and purified enzyme from Rhizopus oryzae on waste cooking oil (sunflower oil). Waste management (New York, N.Y.). 2012 Aug; 32(8):1539-47. doi: 10.1016/j.wasman.2012.03.011. [PMID: 22537973]
  • 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]
  • Jana Cimlová, Pavla Kružberská, Zdeněk Švagera, Petr Hušek, Petr Šimek. In situ derivatization-liquid liquid extraction as a sample preparation strategy for the determination of urinary biomarker prolyl-4-hydroxyproline by liquid chromatography-tandem mass spectrometry. Journal of mass spectrometry : JMS. 2012 Mar; 47(3):294-302. doi: 10.1002/jms.2952. [PMID: 22431455]
  • Randor Radakovits, Robert E Jinkerson, Susan I Fuerstenberg, Hongseok Tae, Robert E Settlage, Jeffrey L Boore, Matthew C Posewitz. Draft genome sequence and genetic transformation of the oleaginous alga Nannochloropis gaditana. Nature communications. 2012 Feb; 3(?):686. doi: 10.1038/ncomms1688. [PMID: 22353717]
  • Vassiliki A Boumba, Vangelis Economou, Nikolaos Kourkoumelis, Panagiota Gousia, Chrissanthy Papadopoulou, Theodore Vougiouklakis. Microbial ethanol production: experimental study and multivariate evaluation. Forensic science international. 2012 Feb; 215(1-3):189-98. doi: 10.1016/j.forsciint.2011.03.003. [PMID: 21470803]
  • Rahele Ghanbari, Farooq Anwar, Khalid M Alkharfy, Anwarul-Hassan Gilani, Nazamid Saari. Valuable nutrients and functional bioactives in different parts of olive (Olea europaea L.)-a review. International journal of molecular sciences. 2012; 13(3):3291-3340. doi: 10.3390/ijms13033291. [PMID: 22489153]
  • Arnaud Taton, Ewa Lis, Dawn M Adin, Guogang Dong, Scott Cookson, Steve A Kay, Susan S Golden, James W Golden. Gene transfer in Leptolyngbya sp. strain BL0902, a cyanobacterium suitable for production of biomass and bioproducts. PloS one. 2012; 7(1):e30901. doi: 10.1371/journal.pone.0030901. [PMID: 22292073]
  • Ekaterina A Savrasova, Aleksander D Kivero, Rustem S Shakulov, Nataliya V Stoynova. Use of the valine biosynthetic pathway to convert glucose into isobutanol. Journal of industrial microbiology & biotechnology. 2011 Sep; 38(9):1287-94. doi: 10.1007/s10295-010-0907-2. [PMID: 21161324]
  • Akemi Ogasawara, Yoshiki Murakami, Nobumasa Yakushiji, Fuminori Ohsawa, Jun-Ichi Kusaba, Tetsuya Aiba, Yuji Kurosaki, Hiroki Kakuta. Pharmacokinetic properties of newly synthesized retinoid X receptor agonists possessing a 6-[N-ethyl-N-(3-alkoxy-4-isopropylphenyl)amino]nicotinic acid skeleton in rats. Drug development and industrial pharmacy. 2011 Sep; 37(9):1060-7. doi: 10.3109/03639045.2011.559247. [PMID: 21417609]
  • Shiyuan Hu, Huajun Zheng, Yang Gu, Jingbo Zhao, Weiwen Zhang, Yunliu Yang, Shengyue Wang, Guoping Zhao, Sheng Yang, Weihong Jiang. Comparative genomic and transcriptomic analysis revealed genetic characteristics related to solvent formation and xylose utilization in Clostridium acetobutylicum EA 2018. BMC genomics. 2011 Feb; 12(?):93. doi: 10.1186/1471-2164-12-93. [PMID: 21284892]
  • Laura R Jarboe. YqhD: a broad-substrate range aldehyde reductase with various applications in production of biorenewable fuels and chemicals. Applied microbiology and biotechnology. 2011 Jan; 89(2):249-57. doi: 10.1007/s00253-010-2912-9. [PMID: 20924577]
  • Ludmila V Roze, Anindya Chanda, Maris Laivenieks, Randolph M Beaudry, Katherine A Artymovich, Anna V Koptina, Deena W Awad, Dina Valeeva, Arthur D Jones, John E Linz. Volatile profiling reveals intracellular metabolic changes in Aspergillus parasiticus: veA regulates branched chain amino acid and ethanol metabolism. BMC biochemistry. 2010 Aug; 11(?):33. doi: 10.1186/1471-2091-11-33. [PMID: 20735852]
  • Małgorzata Jakubowicz, Hanna Gałgańska, Witold Nowak, Jan Sadowski. Exogenously induced expression of ethylene biosynthesis, ethylene perception, phospholipase D, and Rboh-oxidase genes in broccoli seedlings. Journal of experimental botany. 2010 Jul; 61(12):3475-91. doi: 10.1093/jxb/erq177. [PMID: 20581125]
  • Miklós Tóth, István Szarukán, Béla Dorogi, Attila Gulyás, Pál Nagy, Zoltán Rozgonyi. Male and female noctuid moths attracted to synthetic lures in Europe. Journal of chemical ecology. 2010 Jun; 36(6):592-8. doi: 10.1007/s10886-010-9789-z. [PMID: 20449640]
  • Itay Gonda, Einat Bar, Vitaly Portnoy, Shery Lev, Joseph Burger, Arthur A Schaffer, Ya'akov Tadmor, Shimon Gepstein, James J Giovannoni, Nurit Katzir, Efraim Lewinsohn. Branched-chain and aromatic amino acid catabolism into aroma volatiles in Cucumis melo L. fruit. Journal of experimental botany. 2010 Feb; 61(4):1111-23. doi: 10.1093/jxb/erp390. [PMID: 20065117]
  • Zofia E Gagnon, Sherry Dingman, Rhys N Thomas. Fluorine-tagged 5-hydroxytryptophan to investigate amino Acid metabolism in vivo. Journal of amino acids. 2010; 2010(?):265069. doi: 10.4061/2010/265069. [PMID: 22331995]
  • Laura R Jarboe, Xueli Zhang, Xuan Wang, Jonathan C Moore, K T Shanmugam, Lonnie O Ingram. Metabolic engineering for production of biorenewable fuels and chemicals: contributions of synthetic biology. Journal of biomedicine & biotechnology. 2010; 2010(?):761042. doi: 10.1155/2010/761042. [PMID: 20414363]
  • Shota Atsumi, Wendy Higashide, James C Liao. Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde. Nature biotechnology. 2009 Dec; 27(12):1177-80. doi: 10.1038/nbt.1586. [PMID: 19915552]
  • Fany Chronidou, Efstratios Apostolakis, Ioannis Papapostolou, Konstantinos Grintzalis, Christos D Georgiou, Efstratios N Koletsis, Menelaos Karanikolas, Panagiotis Papathanasopoulos, Dimitrios Dougenis. Beneficial effect of the oxygen free radical scavenger amifostine (WR-2721) on spinal cord ischemia/reperfusion injury in rabbits. Journal of cardiothoracic surgery. 2009 Sep; 4(?):50. doi: 10.1186/1749-8090-4-50. [PMID: 19758462]
  • Marcello Civilini. Identification and characterization of bacteria isolated under selective pressure of volatile organic compounds. Journal of environmental biology. 2009 Jan; 30(1):99-105. doi: ". [PMID: 20112870]
  • Maaike Bruinsma, Maarten A Posthumus, Roland Mumm, Martin J Mueller, Joop J A van Loon, Marcel Dicke. Jasmonic acid-induced volatiles of Brassica oleracea attract parasitoids: effects of time and dose, and comparison with induction by herbivores. Journal of experimental botany. 2009; 60(9):2575-87. doi: 10.1093/jxb/erp101. [PMID: 19451186]
  • Mahiran Basri, Raja Noor Zaliha Raja Abd Rahman, Afshin Ebrahimpour, Abu Bakar Salleh, Erin Ryantin Gunawan, Mohd Basyaruddin Abd Rahman. Comparison of estimation capabilities of response surface methodology (RSM) with artificial neural network (ANN) in lipase-catalyzed synthesis of palm-based wax ester. BMC biotechnology. 2007 Aug; 7(?):53. doi: 10.1186/1472-6750-7-53. [PMID: 17760990]
  • Roni Vicente Reche, Alexandre Ferreira Leite Neto, Alexandre Ataide Da Silva, Carlos Alexandre Galinaro, Renata Zachi De Osti, Douglas Wagner Franco. Influence of type of distillation apparatus on chemical profiles of brazilian cachaças. Journal of agricultural and food chemistry. 2007 Aug; 55(16):6603-8. doi: 10.1021/jf0704110. [PMID: 17629298]
  • Megan D Reeves, Adam K Schawel, Weidong Wang, Phoebe Dea. Effects of butanol isomers on dipalmitoylphosphatidylcholine bilayer membranes. Biophysical chemistry. 2007 Jun; 128(1):13-8. doi: 10.1016/j.bpc.2007.02.004. [PMID: 17368700]
  • Bengu Cobanoglu, Ibrahim H Ozercan, M Resat Ozercan, Orhan Yalcin. The effect of inhaling thinner and/or cigarette smoke on rat kidneys. Inhalation toxicology. 2007 Mar; 19(3):303-8. doi: 10.1080/08958370601141890. [PMID: 17365033]
  • Gudrun Olafsdottir, Rosa Jonsdottir, Hélène L Lauzon, Joop Luten, Kristberg Kristbergsson. Characterization of volatile compounds in chilled cod (Gadus morhua) fillets by gas chromatography and detection of quality indicators by an electronic nose. Journal of agricultural and food chemistry. 2005 Dec; 53(26):10140-7. doi: 10.1021/jf0517804. [PMID: 16366707]
  • Daniel R Cardoso, Luiz G Andrade-Sobrinho, Alexandre F Leite-Neto, Roni V Reche, William D Isique, Marcia M C Ferreira, Benedito S Lima-Neto, Douglas W Franco. Comparison between cachaça and rum using pattern recognition methods. Journal of agricultural and food chemistry. 2004 Jun; 52(11):3429-33. doi: 10.1021/jf035262+. [PMID: 15161210]
  • Kanako Watanabe-Suzuki, Hideki Nozawa, Osamu Suzuki, Akira Ishii. Sensitive analysis of alkyl alcohols as decomposition products of alkyl nitrites in human whole blood and urine by headspace capillary GC with cryogenic oven trapping. Journal of chromatographic science. 2003 Feb; 41(2):63-6. doi: 10.1093/chromsci/41.2.63. [PMID: 12639252]
  • Katumi Umano, Yukio Hagi, Takayuki Shibamoto. Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.). Journal of agricultural and food chemistry. 2002 Sep; 50(19):5355-9. doi: 10.1021/jf0203951. [PMID: 12207474]
  • Bruno Spinosa De Martinis, Carmen Cinira Santos Martin. Automated headspace solid-phase microextraction and capillary gas chromatography analysis of ethanol in postmortem specimens. Forensic science international. 2002 Aug; 128(3):115-9. doi: 10.1016/s0379-0738(02)00182-2. [PMID: 12175789]
  • I M Roberts. Iso-butanol saturated water: a simple procedure for increasing staining intensity of resin sections for light and electron microscopy. Journal of microscopy. 2002 Aug; 207(Pt 2):97-107. doi: 10.1046/j.1365-2818.2002.01045.x. [PMID: 12180955]
  • R Iffland, A W Jones. Evaluating alleged drinking after driving--the hip-flask defence. Part 1. Double blood samples and urine-to-blood alcohol relationship. Medicine, science, and the law. 2002 Jul; 42(3):207-24. doi: 10.1177/002580240204200305. [PMID: 12201066]
  • B Yavo, I L Brunetti, L M da Fonseca, L H Catalani, A Campa. Selective activity of butyrylcholinesterase in serum by a chemiluminescent assay. Luminescence : the journal of biological and chemical luminescence. 2001 Sep; 16(5):299-304. doi: 10.1002/bio.658. [PMID: 11590700]
  • S Kramer, G Blaschke. High-performance liquid chromatographic determination of the beta2-selective adrenergic agonist fenoterol in human plasma after fluorescence derivatization. Journal of chromatography. B, Biomedical sciences and applications. 2001 Feb; 751(1):169-75. doi: 10.1016/s0378-4347(00)00468-0. [PMID: 11232847]
  • C Fuke, C L Berry, D J Pounder. Postmortem diffusion of ingested and aspirated paint thinner. Forensic science international. 1996 Apr; 78(3):199-207. doi: 10.1016/0379-0738(96)01889-0. [PMID: 8635764]
  • M E Morris, S B Hansel. High-performance liquid chromatographic analysis of p-nitrophenol and its conjugates in biological samples. Journal of chromatography. 1990 Nov; 532(2):285-93. doi: 10.1016/s0378-4347(00)83779-2. [PMID: 2084126]