2.0 2012-05-31 13:54:48 -0600 2015-09-13 12:56:11 -0600 ECMDB01875 M2MDB000425 Methanol Methanol is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol. It is produced naturally in the anaerobic metabolism of many varieties of bacteria, and is ubiquitous in the environment. As a result, there is a small fraction of methanol vapor in the atmosphere. (Wikipedia). Alcool methylique Alcool metilico Carbinol CH3OH Colonial spirit Columbian spirit Columbian spirits Hydroxymethane MeOH Metanolo Methanol Methanol-water mixture Methyl alcohol Methyl hydroxide Methylalkohol Methylol MetOH Metylowy alkohol Monohydroxymethane Pyro alcohol Pyroxylic spirit Spirit of wood Wood alcohol Wood naphtha Wood spirit CH4O 32.0419 32.02621475 methanol methanol 67-56-1 CO InChI=1S/CH4O/c1-2/h2H,1H3 OKKJLVBELUTLKV-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp -1.38 ALOGPS logs 1.21 ALOGPS solubility 5.19e+02 g/l ALOGPS melting_point -97.6 oC logp -0.52 ChemAxon pka_strongest_acidic 15.78 ChemAxon pka_strongest_basic -2.5 ChemAxon iupac methanol ChemAxon average_mass 32.0419 ChemAxon mono_mass 32.02621475 ChemAxon smiles CO ChemAxon formula CH4O ChemAxon inchi InChI=1S/CH4O/c1-2/h2H,1H3 ChemAxon inchikey OKKJLVBELUTLKV-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 8.26 ChemAxon polarizability 3.38 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Methane metabolism ec00680 Pentose and glucuronate interconversions ec00040 Drug metabolism - other enzymes ec00983 Biotin metabolism Biotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase.In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with a malonyl-[acp] interacting with S-adenosylmethionine through a biotin synthesis protein BioC resulting in a S-adenosylhomocysteine and a malonyl-[acp] methyl ester. The latter compound is then involved in the synthesis of a 3-ketoglutaryl-[acp] methyl ester through a 3-oxoacyl-[acyl-carrier-protein] synthase. The compound 3-ketoglutaryl-[acp] methyl ester is reduced by a NADPH mediated 3-oxoacyl-[acyl-carrier-protein] reductase resulting in a 3R-hydroxyglutaryl-[acp] methyl ester. This compound is then dehydrated through ad (3R)-hydroxymyristoyl-[acp] dehydratase producing a enoylglutaryl-[acp] methyl ester. This compound is then reduced through a NADPH mediated enoyl-acp-reductase [NADH] resulting in a glutaryl-[acp] methyl ester. This compound interacts with a malonyl-[acp] through a 3-oxoacyl-[acp] synthase 2 resulting in a 3-ketopimeloyl [acp] methyl ester. This compound is then reduced through a NADPH 3-oxoacyl [acp] reductase producing a 3-hydroxypimeloyl-[acp] methyl ester and then dehydrated by (3R)-hydroxymyristoyl-[acp] dehydratase to produce a enoylpimeloyl-[acp] methyl ester. This compound is then reduced by a NADPH dependent enoyl-[acp]reductase resulting in a pimeloyl-[acp] methyl ester. This compound then reacts with water through a carboxylesterase resulting in a pimeloyl-[acp] and a methanol. The pimeloyl-acp reacts with L-alanine through a 8-amino-7-oxononanoate synthase resulting in 8-amino-7-oxononanoate which in turn reacts with S-adenosylmethionine through a 7,8 diaminonanoate transaminase resulting in a S-adenosyl-4-methylthio-2-oxobutanoate and 7,8 diaminononanoate. The latter compound is then dephosphorylated through a dethiobiotin synthetase resulting in a dethiobiotin. This compound interacts with a sulfurated[sulfur carrier), a hydrogen ion and a S-adenosylmethionine through a biotin synthase to produce Biotin and releasing l-methionine and a 5-deoxyadenosine. Biotin is then metabolized by a bifunctional protein resulting in pyrophosphate and Biotinyl-5-AMP which in turn reacts with the same protein (bifunctional protein birA resulting ina biotin caroxyl carrying protein.This product then enters the fatty acid biosynthesis. PW000762 ec00780 Metabolic Microbial metabolism in diverse environments ec01120 Two-component system ec02020 Metabolic pathways eco01100 7-keto-8-aminopelargonate biosynthesis I PWY-6519 Specdb::CMs 20569 Specdb::CMs 29321 Specdb::CMs 29529 Specdb::CMs 38162 Specdb::CMs 99719 Specdb::CMs 99720 Specdb::CMs 165242 Specdb::EiMs 939 Specdb::NmrOneD 1773 Specdb::NmrOneD 2575 Specdb::NmrOneD 3271 Specdb::NmrOneD 9802 Specdb::NmrOneD 9803 Specdb::NmrOneD 9804 Specdb::NmrOneD 9805 Specdb::NmrOneD 9806 Specdb::NmrOneD 9807 Specdb::NmrOneD 9808 Specdb::NmrOneD 9809 Specdb::NmrOneD 9810 Specdb::NmrOneD 9811 Specdb::NmrOneD 9812 Specdb::NmrOneD 9813 Specdb::NmrOneD 9814 Specdb::NmrOneD 9815 Specdb::NmrOneD 9816 Specdb::NmrOneD 9817 Specdb::NmrOneD 9818 Specdb::NmrOneD 9819 Specdb::NmrOneD 9820 Specdb::NmrOneD 9821 Specdb::MsMs 1768 Specdb::MsMs 1769 Specdb::MsMs 1770 Specdb::MsMs 5532 Specdb::MsMs 20492 Specdb::MsMs 20493 Specdb::MsMs 20494 Specdb::MsMs 22043 Specdb::MsMs 22044 Specdb::MsMs 22045 Specdb::MsMs 2298501 Specdb::MsMs 2298502 Specdb::MsMs 2298503 Specdb::MsMs 2637622 Specdb::MsMs 2637623 Specdb::MsMs 2637624 Specdb::NmrTwoD 1092 Specdb::NmrTwoD 1713 HMDB01875 887 864 C00132 17790 METOH OME Methanol Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. 12097436 Nagasawa H, Wada M, Koyama S, Kawanami T, Kurita K, Kato T: [A case of methanol intoxication with optic neuropathy visualized on STIR sequence of MR images] Rinsho Shinkeigaku. 2005 Jul;45(7):527-30. 16119839 Ferrari LA, Arado MG, Nardo CA, Giannuzzi L: Post-mortem analysis of formic acid disposition in acute methanol intoxication. Forensic Sci Int. 2003 Apr 23;133(1-2):152-8. 12742704 Avella J, Briglia E, Harleman G, Lehrer M: Percutaneous absorption and distribution of methanol in a homicide. J Anal Toxicol. 2005 Oct;29(7):734-7. 16419410 Bogdanov-Berezovsky A, Glesinger R, Kachko L, Arbel E, Rosenberg L, Grossman N: Accreditation of skin from a methanol-poisoned victim for banking and grafting. Transplantation. 2002 Jun 27;73(12):1913-7. 12131687 Heinig K, Henion J: Determination of carnitine and acylcarnitines in biological samples by capillary electrophoresis-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Dec 10;735(2):171-88. 10670733 Kaphalia BS, Carr JB, Ansari GA: Increased endobiotic fatty acid methyl esters following exposure to methanol. Fundam Appl Toxicol. 1995 Dec;28(2):264-73. 8835236 Batterman SA, Franzblau A, Zhou N: Airborne emissions at skin surfaces: a potential biological exposure index. Int Arch Occup Environ Health. 1996;68(4):268-74. 8738358 Vassiliadis J, Graudins A, Dowsett RP: Triethylene glycol poisoning treated with intravenous ethanol infusion. J Toxicol Clin Toxicol. 1999;37(6):773-6. 10584590 Lee XP, Kumazawa T, Kondo K, Sato K, Suzuki O: Analysis of methanol or formic acid in body fluids by headspace solid-phase microextraction and capillary gas chromatography. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):155-62. 10574201 Jose N, Ajith TA, Janardhanan KK: Methanol extract of the oyster mushroom, Pleurotus florida, inhibits inflammation and platelet aggregation. Phytother Res. 2004 Jan;18(1):43-6. 14750200 Comoglu S, Ozen B, Ozbakir S: Methanol intoxication with bilateral basal ganglia infarct. Australas Radiol. 2001 Aug;45(3):357-8. 11531765 Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, van Breemen RB: Human, rat, and mouse metabolism of resveratrol. Pharm Res. 2002 Dec;19(12):1907-14. 12523673 Keum YS, Park KK, Lee JM, Chun KS, Park JH, Lee SK, Kwon H, Surh YJ: Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 2000 Mar 13;150(1):41-8. 10755385 Megarbane B, Borron SW, Baud FJ: Current recommendations for treatment of severe toxic alcohol poisonings. Intensive Care Med. 2005 Feb;31(2):189-95. Epub 2004 Dec 31. 15627163 Purssell RA, Lynd LD, Koga Y: The use of the osmole gap as a screening test for the presence of exogenous substances. Toxicol Rev. 2004;23(3):189-202. 15862085 Cummings, Donald Ray. Process for production of methanol from a methane gas stream. PCT Int. Appl. (2007), 21pp. http://hmdb.ca/system/metabolites/msds/000/001/466/original/HMDB01875.pdf?1358462830 Chemotaxis response regulator protein-glutamate methylesterase P07330 CHEB_ECOLI cheB http://ecmdb.ca/proteins/P07330.xml Carboxylesterase BioH P13001 BIOH_ECOLI bioH http://ecmdb.ca/proteins/P13001.xml Catalase-peroxidase P13029 KATG_ECOLI katG http://ecmdb.ca/proteins/P13029.xml Catalase HPII P21179 CATE_ECOLI katE http://ecmdb.ca/proteins/P21179.xml Putative acyl-CoA thioester hydrolase ybhC P46130 YBHC_ECOLI ybhC http://ecmdb.ca/proteins/P46130.xml acetyl esterase (EC:3.1.1.-) P23872 aes http://ecmdb.ca/proteins/P23872.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Water + Pimeloyl-[acyl-carrier protein] methyl ester > Methanol + Pimeloyl-[acyl-carrier protein] Methanol + Hydrogen peroxide <> Formaldehyde +2 Water R00602 L-Lyxose + Water <> Methanol + Pectic acid R02362 Ecgonine methyl ester + Water <> Ecgonine + Methanol R06729 Pimelyl-[acyl-carrier protein] methyl ester + Water + Pimeloyl-[acyl-carrier protein] methyl ester <> Pimelyl-[acyl-carrier protein] + Methanol + Pimeloyl-[acyl-carrier protein] R09725 Pimelyl-[acyl-carrier protein] methyl ester + Water > pimelyl-[acyl-carrier protein] + Methanol Protein L-glutamate O(5)-methyl ester + Water > protein L-glutamate + Methanol Pectin + Water <> Methanol + Pectic acid R02362 R06250 Protein glutamate methyl ester + Water <> Protein glutamate + Methanol R02624 a pimeloyl-[acp] methyl ester + Water > Methanol + a pimeloyl-[acp] PW_R002465 Protein glutamate methyl ester + Water <> Protein glutamate + Methanol