ECMDB: Methanol (ECMDB01875) (M2MDB000425)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)Transporters (4)XML

Proteins (779)

Record Information

Version

2.0

Creation Date

2012-05-31 13:54:48 -0600

Update Date

2015-09-13 12:56:11 -0600

Secondary Accession Numbers

ECMDB01875

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D 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

Weight:

Average: 32.0419
Monoisotopic: 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:

Chemical Taxonomy

Description

belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:17790 )
primary alcohol (CHEBI:17790 )
alkyl alcohol (CHEBI:17790 )
a short-chain alcohol (METOH )

Physical Properties

State:

Liquid

Charge:

Melting point:

-97.6 °C

Experimental Properties:

Property	Value	Source
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

Property	Value	Source
Water Solubility	519 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.52	ChemAxon
logS	1.21	ALOGPS
pKa (Strongest Acidic)	15.78	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	8.26 m³·mol⁻¹	ChemAxon
Polarizability	3.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Biotin metabolism	PW000762
Starch and sucrose metabolism	PW000941

KEGG Pathways:

Biotin metabolism ec00780
Drug metabolism - other enzymes ec00983
Metabolic pathways eco01100
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120
Pentose and glucuronate interconversions ec00040
Starch and sucrose metabolism ec00500
Tropane, piperidine and pyridine alkaloid biosynthesis ec00960
Two-component system ec02020

EcoCyc Pathways:

7-keto-8-aminopelargonate biosynthesis I PWY-6519

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-2173f5595be586c5c940	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-14ea8d185227ede9bff7	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-2173f5595be586c5c940	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-14ea8d185227ede9bff7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-4c6569479bda044bbec6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9000000000-7cc6047a4db3644c3b83	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0000-0000000000-e3b0c44298fc1c149afb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-6d633534165eedf07b4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-757b6964771196ee308f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-001i-9000000000-fef92d3f671a9282b5a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-60e278e17032d30c1c8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-60e278e17032d30c1c8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-60e278e17032d30c1c8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-9d3a102faa7d9058eb88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-9d3a102faa7d9058eb88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-9d3a102faa7d9058eb88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-8071a59ff1eb417f4a9a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-8071a59ff1eb417f4a9a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-8071a59ff1eb417f4a9a	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-5a9d4ce5dca0ae1a6765	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

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)

Links

External Links:

Resource	Link
CHEBI ID	17790
HMDB ID	HMDB01875
Pubchem Compound ID	887
Kegg ID	C00132
ChemSpider ID	864
Wikipedia	Methanol
BioCyc ID	METOH
EcoCyc ID	METOH
Ligand Expo	OME

Enzymes

Protein Details

1. 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
Uniprot ID:: P07330
Molecular weight:: 37467

Reactions

Protein L-glutamate O(5)-methyl ester + H(2)O = protein L-glutamate + methanol.

Protein Details

2. Carboxylesterase BioH

General function:: Involved in biotin biosynthetic process
Specific function:: Shows carboxylesterase activity with a preference for short chain fatty acid esters (acyl chain length of up to 6 carbons). Also displays a weak thioesterase activity. Can form a complex with CoA, and may be involved in the condensation of CoA and pimelic acid into pimeloyl-CoA, a precursor in biotin biosynthesis
Gene Name:: bioH
Uniprot ID:: P13001
Molecular weight:: 28505

Reactions

Pimelyl-[acyl-carrier protein] methyl ester + H(2)O = pimelyl-[acyl-carrier protein] + methanol.

Protein Details

3. Catalase-peroxidase

General function:: Involved in catalase activity
Specific function:: Bifunctional enzyme with both catalase and broad- spectrum peroxidase activity. Displays also NADH oxidase, INH lyase and isonicotinoyl-NAD synthase activity
Gene Name:: katG
Uniprot ID:: P13029
Molecular weight:: 80023

Reactions

Donor + H(2)O(2) = oxidized donor + 2 H(2)O.
2 H(2)O(2) = O(2) + 2 H(2)O.

Protein Details

4. 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
Uniprot ID:: P21179
Molecular weight:: 84162

Reactions

2 H(2)O(2) = O(2) + 2 H(2)O.

Protein Details

5. Putative acyl-CoA thioester hydrolase ybhC

General function:: Involved in pectinesterase activity
Specific function:: Putative thioesterase. Does not bind pectin, and has no pectinesterase activity
Gene Name:: ybhC
Uniprot ID:: P46130
Molecular weight:: 46082

Protein Details

6. acetyl esterase (EC:3.1.1.-)

General function:: Not Available
Specific function:: Not Available
Gene Name:: aes
Uniprot ID:: P23872
Molecular weight:: Not Available

Transporters

Protein Details

1. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

2. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

3. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

4. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Methanol (ECMDB01875) (M2MDB000425)

Structure for #<Compound:0xa85f325c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters