2-methylbutan-1-ol (YMDB00567)

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Identification

YMDB ID

YMDB00567

Name

2-methylbutan-1-ol

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

(S)-2-Methyl-1-butanol, also known as 2-methyl butanol-1 or 2-methylbutyl alcohol, 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 (S)-2-Methyl-1-butanol exists in all eukaryotes, ranging from yeast to plants to humans. In yeast, (S)-2-methyl-1-butanol is involved in the metabolic pathway called the isoleucine degradation pathway. Based on a literature review a significant number of articles have been published on (S)-2-Methyl-1-butanol.

Structure

MOL SDF PDB SMILES InChI

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 number

137-32-6

Weight

Average: 88.1482
Monoisotopic: 88.088815006

InChI Key

QPRQEDXDYOZYLA-UHFFFAOYSA-N

InChI

InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3

IUPAC Name

2-methylbutan-1-ol

Traditional IUPAC Name

2-methyl-1-butanol

Chemical Formula

C₅H₁₂O

SMILES

CCC(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).

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

primary alcohol (CHEBI:48945 )
alkyl alcohol (CHEBI:48945 )
Fatty alcohols (LMFA05000104 )
a small molecule (CPD-7033 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	29.7 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.29 [VALVANI,SC ET AL. (1981)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	42 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.17	ChemAxon
logS	-0.32	ALOGPS
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	-1.7	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	2	ChemAxon
Refractivity	26.61 m³·mol⁻¹	ChemAxon
Polarizability	10.99 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

extracellular
mitochondrion
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Malt	FDB008130

SMPDB Pathways

Isoleucine degradation

PW002491

KEGG Pathways

Not 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 Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-4710deb4dee4bfd03754	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-7171709ce52ea140418d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-69d3eb6fa5d3cbace4d2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-4710deb4dee4bfd03754	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-7171709ce52ea140418d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-69d3eb6fa5d3cbace4d2	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-02e9885c21b53d9d6349	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fi1-9400000000-11c9785b27e999fdfef3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-9000000000-128169279e6dbc93647d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-dc20fc6a9edf20c015c0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-c22c4d3aed422eaa3d6c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-9000000000-128169279e6dbc93647d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-dc20fc6a9edf20c015c0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-c22c4d3aed422eaa3d6c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-3755227e402feb51b4de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-fcef5652b712c7416e06	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-52f93c4b7493a853c052	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-3755227e402feb51b4de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-fcef5652b712c7416e06	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-52f93c4b7493a853c052	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-dd8f1f11d4928285c04e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1bcbc03c82fd267687cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-aa0f0ceef51269cb75e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-ef8ab8a1e6e9f7d8ca2f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-fe19acc4abf9392ddb73	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-266852879b8ed1e050f1	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-354c4fb764d5125305e7	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	48945
HMDB ID	HMDB0031527
Pubchem Compound ID	8723
Kegg ID	Not Available
ChemSpider ID	8398
FOODB ID	FDB008130
Wikipedia ID	Not Available
BioCyc ID	Not 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

Structure for #<Compound:0xa2516114>

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