3-methylbutanal (YMDB00499)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Identification

YMDB ID

YMDB00499

Name

3-methylbutanal

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Isovaleraldehyde, also known as beta-methylbutanal or iso-C4H9CHO, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. Isovaleraldehyde exists in all eukaryotes, ranging from yeast to plants to humans. In yeast, isovaleraldehyde is involved in the metabolic pathway called the leucine degradation pathway. Based on a literature review a significant number of articles have been published on Isovaleraldehyde.

Structure

MOL SDF PDB SMILES InChI

Synonyms

β-Methylbutanal
1-Butanal, 3-methyl-
2-Methylbutanal-4
3-methyl-1-Butanal
3-methyl-Butanal
3-methyl-Butyraldehyde
3-Methylbutan-1-al
3-Methylbutanal
3-Methylbutyraldehyde
b-Methylbutanal
beta-methylbutanal
Butanal, 3-methyl-
Butyraldehyde, 3-methyl-
Isoamyl aldehyde
Isoamylaldehyde
Isopentaldehyde
Isopentanal
Isovaleral
Isovaleraldehyde
Isovaleric aldehyde
Isovalerylaldehyde
Methyl butanal
Iso-C4H9CHO
Β-methylbutanal
iso-Valeraldehyde

CAS number

590-86-3

Weight

Average: 86.1323
Monoisotopic: 86.073164942

InChI Key

YGHRJJRRZDOVPD-UHFFFAOYSA-N

InChI

InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3

IUPAC Name

3-methylbutanal

Traditional IUPAC Name

isovaleraldehyde

Chemical Formula

C₅H₁₀O

SMILES

CC(C)CC=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methylbutanal (CHEBI:16638 )
a small molecule (CPD-7031 )

Physical Properties

State

Liquid

Charge

Melting point

-51 °C

Experimental Properties

Property	Value	Reference
Water Solubility	14 mg/mL at 20 oC [FALBE,J et al. (1985)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	17 g/L	ALOGPS
logP	1.29	ALOGPS
logP	1.05	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	18.56	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.49 m³·mol⁻¹	ChemAxon
Polarizability	10.12 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
Aldehydic	FDB003285
Chocolate	FDB003285
Ethereal	FDB003285
Fatty	FDB003285
Malt	FDB003285
Peach	FDB003285
Sour	FDB003285

SMPDB Pathways

Leucine Degradation

PW002490

KEGG Pathways

Not Available

SMPDB Reactions

3-methylbutanal + NADH + hydron ↔ NAD + isoamylol

Ketoleucine + hydron → 3-methylbutanal + Carbon dioxide

KEGG Reactions

Ketoleucine + hydron → Carbon dioxide + 3-methylbutanal

NADH + 3-methylbutanal + hydron → NAD + isoamylol

3-methylbutanal + NADPH + hydron → NADP + isoamylol

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)	splash10-0006-9000000000-3a38c8f6150bf1f43e74	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-3a38c8f6150bf1f43e74	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-4b322dc8237378d93057	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-7f4ac528265c8b3bf3ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-6e4f25dc68765a0e52ca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-809684cd2152204e911f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-3a38c8f6150bf1f43e74	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-a8ed71d6e7d567b598b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kp-9000000000-043451832d2f37b1c7e1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3c57d920ca714b174bb3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-030536579800c9e49940	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-be1f1229d7e13994d150	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-13768c049fd8e5c23464	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-a8ed71d6e7d567b598b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kp-9000000000-043451832d2f37b1c7e1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3c57d920ca714b174bb3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-030536579800c9e49940	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-be1f1229d7e13994d150	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-13768c049fd8e5c23464	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2091e44a102d8284a813	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-199420ebca1b5eda6369	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-0f801351f709d0e5abf6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-fead34b12404197f107d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-cf72963a4f1f9f7f2df0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cd0a0aa8e74bbc2b6344	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-881fcc89b0f579b40793	JSpectraViewer \| MoNA
1D NMR	1H 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
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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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
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
Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
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
Larroy, C., Fernandez, M. R., Gonzalez, E., Pares, X., Biosca, J. A. (2002). "Characterization of the Saccharomyces cerevisiae YMR318C (ADH6) gene product as a broad specificity NADPH-dependent alcohol dehydrogenase: relevance in aldehyde reduction." Biochem J 361:163-172.11742541
Hauser, M., Horn, P., Tournu, H., Hauser, N. C., Hoheisel, J. D., Brown, A. J., Dickinson, J. R. (2007). "A transcriptome analysis of isoamyl alcohol-induced filamentation in yeast reveals a novel role for Gre2p as isovaleraldehyde reductase." FEMS Yeast Res 7:84-92.16999827

Synthesis Reference:

Roelen, O. Synthesis of aldehydes and derivatives from olefins, carbon monoxide, and hydrogen. Angew. Chem. (1948), A60 62. CAN 44:46679 AN 1950:46679

External Links:

Resource	Link
CHEBI ID	16638
HMDB ID	HMDB06478
Pubchem Compound ID	7284
Kegg ID	C07329
ChemSpider ID	11065
FOODB ID	FDB003285
Wikipedia ID	Isovaleraldehyde
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. NADPH-dependent methylglyoxal reductase GRE2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the irreversible reduction of the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde as an alternative to detoxification of MG by glyoxalase I GLO1. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation
Gene Name:: GRE2
Uniprot ID:: Q12068
Molecular weight:: 38169.19922

Reactions

Lactaldehyde + NADP(+) → methylglyoxal + NADPH.
3-methylbutanol + NAD(P)+ → 3-methylbutanal + NAD(P)H + H+

Protein Details

8. 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

9. 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

10. Transaminated amino acid decarboxylase

General function:: Involved in magnesium ion binding
Specific function:: One of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) involved in amino acid catabolism. The enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids (alpha-keto-acids). In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids, phenylalanine, tryptophan, (and probably tyrosine), but also isoleucine, whereas leucine is a low efficiency and valine and pyruvate are no substrates. In analogy to the pyruvate decarboxylases the enzyme may in a side-reaction catalyze condensation (or carboligation) reactions leading to the formation of 2-hydroxy ketone, collectively called acyloins
Gene Name:: ARO10
Uniprot ID:: Q06408
Molecular weight:: 71383.79688

Reactions

A 2-oxo acid → an aldehyde + CO(2).
Phenylpyruvate → phenylacetaldehyde + CO(2).
3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2).

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. Thiamine metabolism regulatory protein THI3

General function:: Involved in magnesium ion binding
Specific function:: One of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) involved in amino acid catabolism. The enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids (alpha-keto-acids). In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids leucine and isoleucine, whereas valine, aromatic amino acids, and pyruvate are no substrates. In analogy to the pyruvate decarboxylases the enzyme may in a side-reaction catalyze condensation (or carboligation) reactions leading to the formation of 2-hydroxy ketone, collectively called acyloins. The enzyme is also positively regulating the thiamine metabolism by a molecular mechanism that may involve thiamine concentration sensing and signal transmission
Gene Name:: THI3
Uniprot ID:: Q07471
Molecular weight:: 68365.79688

Reactions

A 2-oxo acid → an aldehyde + CO(2).

Structure for #<Compound:0xb0a865c8>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions