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2-methylbutan-1-ol (YMDB00567)

Identification
YMDB IDYMDB00567
Name2-methylbutan-1-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-2-Methyl-1-butanol, also known as sec-butylcarbinol or 2-methyl butanol-1, 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). Thus, (S)-2-methyl-1-butanol is considered to be a fatty alcohol lipid molecule (S)-2-Methyl-1-butanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-2-Methyl-1-butanol exists in all eukaryotes, ranging from yeast to humans (S)-2-methyl-1-butanol can be biosynthesized from ()-2-methylbutanal; which is catalyzed by the enzyme alcohol dehydrogenase. In yeast, (S)-2-methyl-1-butanol is involved in the metabolic pathway called the isoleucine degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Butanol, 2-methyl-
  • 2-Methyl butanol-1
  • 2-Methyl-1-butanol
  • 2-methyl-butan-1-ol
  • 2-Methyl-n-butanol
  • 2-Methylbutanol
  • 2-Methylbutyl alcohol
  • 3-methyl iso-butanol
  • Active Amyl alcohol
  • Active primary amyl alcohol
  • Butanol, 2-methyl-
  • dl-2-Methyl-1-butanol
  • dl-sec-Butyl carbinol
  • L-2-Methyl-1-butanol
  • Methyl-2-butan-1-ol
  • Primary active amyl alcohol
  • sec-Butylcarbinol
  • CH3CH2CH(CH3)CH2OH
  • (+/-)-2-methyl-1-butanol
  • (1)-2-Methylbutan-1-ol
  • (S)-(-)-2-Methyl-1-butanol
  • (S)-2-Methylbutan-1-ol
  • 2-Methyl-(.+/-.)-1-butanol
  • 2-Methyl-(2S)-1-butanol
  • 2-Methyl-(S)-1-butanol
  • 2-Methylbutan-1-ol
  • D-2-METHYL-1-butanol
  • DL-2-METHYL-1-butanol, pract
  • Sec-butyl carbinol
CAS number137-32-6
WeightAverage: 88.1482
Monoisotopic: 88.088815006
InChI KeyQPRQEDXDYOZYLA-UHFFFAOYSA-N
InChIInChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3
IUPAC Name2-methylbutan-1-ol
Traditional IUPAC Name2-methyl-1-butanol
Chemical FormulaC5H12O
SMILESCCC(C)CO
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).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility29.7 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.29 [VALVANI,SC ET AL. (1981)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility42 g/LALOGPS
logP1.24ALOGPS
logP1.17ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)17.5ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.61 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
MaltFDB008130
SMPDB Pathways
Isoleucine degradationPW002491 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-Methylbutanal + NADH + hydron → 2-methylbutan-1-ol + NAD
KEGG Reactions
Acetyl-CoA + 2-methylbutan-1-ol → 2-Methylbutyl acetate + Coenzyme A
2-Methylbutanal + NADH + hydron → NAD + 2-methylbutan-1-ol
2-Methylbutanal + NADPH + hydron → NADP + 2-methylbutan-1-ol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-4710deb4dee4bfd03754JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-7171709ce52ea140418dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-69d3eb6fa5d3cbace4d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-4710deb4dee4bfd03754JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-7171709ce52ea140418dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-69d3eb6fa5d3cbace4d2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-02e9885c21b53d9d6349JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fi1-9400000000-11c9785b27e999fdfef3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9000000000-128169279e6dbc93647dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-dc20fc6a9edf20c015c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-c22c4d3aed422eaa3d6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9000000000-128169279e6dbc93647dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-dc20fc6a9edf20c015c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-c22c4d3aed422eaa3d6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-3755227e402feb51b4deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-fcef5652b712c7416e06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-52f93c4b7493a853c052JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-3755227e402feb51b4deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-fcef5652b712c7416e06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-52f93c4b7493a853c052JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-354c4fb764d5125305e7JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ford, G., Ellis, E. M. (2002). "Characterization of Ypr1p from Saccharomyces cerevisiae as a 2-methylbutyraldehyde reductase." Yeast 19:1087-1096.12210903
  • Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
  • Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). "Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry." Proc Natl Acad Sci U S A 104:2193-2198.17287358
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
  • Larroy, C., Pares, X., Biosca, J. A. (2002). "Characterization of a Saccharomyces cerevisiae NADP(H)-dependent alcohol dehydrogenase (ADHVII), a member of the cinnamyl alcohol dehydrogenase family." Eur J Biochem 269:5738-5745.12423374
  • Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID48945
HMDB IDHMDB0031527
Pubchem Compound ID8723
Kegg IDNot Available
ChemSpider ID8398
FOODB IDFDB008130
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Alcohol dehydrogenase 3, mitochondrial
General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH3
Uniprot ID:
P07246
Molecular weight:
40369.19922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
2. S-(hydroxymethyl)glutathione dehydrogenase
General function:
Involved in zinc ion binding
Specific function:
Oxidizes long-chain alcohols and, in the presence of glutathione, is able to oxidize formaldehyde. Is responsible for yeast resistance to formaldehyde
Gene Name:
SFA1
Uniprot ID:
P32771
Molecular weight:
41041.69922
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) → S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
3. Alcohol dehydrogenase 1
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of primary unbranched alcohols to their corresponding aldehydes. Also also shows activity toward secondary alcohols
Gene Name:
ADH1
Uniprot ID:
P00330
Molecular weight:
36849.0
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
4. Alcohol dehydrogenase 4
General function:
Involved in oxidoreductase activity
Specific function:
Reduces acetaldehyde to ethanol during glucose fermentation. Specific for ethanol. Shows drastically reduced activity towards primary alcohols from 4 carbon atoms upward. Isomers of aliphatic alcohol, as well as secondary alcohols and glycerol are not used at all
Gene Name:
ADH4
Uniprot ID:
P10127
Molecular weight:
41141.69922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
5. Alcohol dehydrogenase 5
General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH5
Uniprot ID:
P38113
Molecular weight:
37647.89844
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
6. Alcohol dehydrogenase 2
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of ethanol to acetaldehyde. Acts on a variety of primary unbranched aliphatic alcohols
Gene Name:
ADH2
Uniprot ID:
P00331
Molecular weight:
36731.60156
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
Protein Details
7. Alcohol O-acetyltransferase 1
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Catalyzes the esterification of isoamyl alcohol and various other alcohols by acetyl-CoA
Gene Name:
ATF1
Uniprot ID:
P40353
Molecular weight:
61035.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
Protein Details
8. Alcohol O-acetyltransferase 2
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Acetyl-CoA + an alcohol = CoA + an acetyl ester
Gene Name:
ATF2
Uniprot ID:
P53296
Molecular weight:
61897.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
Protein Details
9. NADP-dependent alcohol dehydrogenase 7
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH7
Uniprot ID:
P25377
Molecular weight:
39348.19922
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
Protein Details
10. Mannosyl phosphorylinositol ceramide synthase regulatory protein CSG2
General function:
Involved in enzyme regulator activity
Specific function:
Required for calcium regulation. May regulate calcium accumulation by a non-vacuole organelle. Also regulates the activity of CSH1 and SUR1 during mannosyl phosphorylinositol ceramide synthesis
Gene Name:
CSG2
Uniprot ID:
P35206
Molecular weight:
45441.60156
Reactions
Protein Details
11. NADP-dependent alcohol dehydrogenase 6
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
Protein Details
12. Putative reductase 1
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
YPR1
Uniprot ID:
Q12458
Molecular weight:
34754.69922
Reactions