Methanol (PAMDB000425)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000425
Identification
Name: Methanol
Description: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).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 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
Chemical Formula: CH4O
Average Molecular Weight: 32.0419
Monoisotopic Molecular Weight: 32.02621475
InChI Key: OKKJLVBELUTLKV-UHFFFAOYSA-N
InChI:InChI=1S/CH4O/c1-2/h2H,1H3
CAS number: 67-56-1
IUPAC Name:methanol
Traditional IUPAC Name: methanol
SMILES:CO
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Alcohols and polyols
Sub ClassPrimary alcohols
Direct Parent Primary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:0
Melting point: -97.6 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]PhysProp
LogP:-0.77 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility519.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-0.52ChemAxon
logS1.21ALOGPS
pKa (Strongest Acidic)15.78ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.26 m3·mol-1ChemAxon
Polarizability3.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Pimeloyl-[acyl-carrier protein] methyl ester > Methanol + Pimeloyl-[acyl-carrier protein]
Methanol + Hydrogen peroxide <> Formaldehyde +2 Water
L-Lyxose + Water <> Methanol + Pectic acid
Ecgonine methyl ester + Water <> Ecgonine + Methanol
Pimelyl-[acyl-carrier protein] methyl ester + Water + Pimeloyl-[acyl-carrier protein] methyl ester <> Pimelyl-[acyl-carrier protein] + Methanol + Pimeloyl-[acyl-carrier protein]
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
Protein glutamate methyl ester + Water <> Protein glutamate + Methanol
a pimeloyl-[acp] methyl ester + Water > Methanol + a pimeloyl-[acp]
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0000-0000000000-e3b0c44298fc1c149afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6d633534165eedf07b4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-757b6964771196ee308fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001i-9000000000-fef92d3f671a9282b5a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-5a9d4ce5dca0ae1a6765View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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. Pubmed: 16419410
  • 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. Pubmed: 8738358
  • 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. Pubmed: 12131687
  • Comoglu S, Ozen B, Ozbakir S: Methanol intoxication with bilateral basal ganglia infarct. Australas Radiol. 2001 Aug;45(3):357-8. Pubmed: 11531765
  • 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. Pubmed: 12742704
  • 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. Pubmed: 10670733
  • 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. Pubmed: 14750200
  • 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. Pubmed: 22080510
  • 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. Pubmed: 8835236
  • 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. Pubmed: 21097882
  • 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. Pubmed: 10755385
  • 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. Pubmed: 10574201
  • 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. Pubmed: 15627163
  • 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. Pubmed: 16119839
  • 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. Pubmed: 15862085
  • 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. Pubmed: 12097436
  • Vassiliadis J, Graudins A, Dowsett RP: Triethylene glycol poisoning treated with intravenous ethanol infusion. J Toxicol Clin Toxicol. 1999;37(6):773-6. Pubmed: 10584590
  • 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. Pubmed: 18331064
  • 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. Pubmed: 12523673
Synthesis Reference: Cummings, Donald Ray. Process for production of methanol from a methane gas stream. PCT Int. Appl. (2007), 21pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17790
HMDB IDHMDB01875
Pubchem Compound ID887
Kegg IDC00132
ChemSpider ID864
WikipediaMethanol
BioCyc IDMETOH
EcoCyc IDMETOH
Ligand ExpoOME

Enzymes

Protein Details
• Chemotaxis response regulator protein-glutamate methylesterase
General function:
Involved in two-component response regulator activity
Specific function:
Involved in the modulation of the chemotaxis system; catalyzes the demethylation of specific methylglutamate residues introduced into the chemoreceptors (methyl-accepting chemotaxis proteins) by CheR
Gene Name:
cheB
Locus Tag:
PA0173
Molecular weight:
37.3 kDa
Reactions
Protein L-glutamate O(5)-methyl ester + H(2)O = protein L-glutamate + methanol.
Protein Details
• Catalase HPII
General function:
Involved in catalase activity
Specific function:
Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
Gene Name:
katE
Locus Tag:
PA2147
Molecular weight:
78 kDa
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.

Transporters