2-Acetolactate (YMDB00394)

Identification

YMDB ID

YMDB00394

Name

2-Acetolactate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

2-Acetolactate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Acetolactate exists in all living species, ranging from bacteria to plants to humans. In yeast, 2-acetolactate is involved in the metabolic pathway called the valine biosynthesis pathway. Based on a literature review a significant number of articles have been published on 2-Acetolactate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-Acetolactate
2-Acetolactic acid

CAS number

Not Available

Weight

Average: 132.1146
Monoisotopic: 132.042258744

InChI Key

NMDWGEGFJUBKLB-UHFFFAOYSA-N

InChI

InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)

IUPAC Name

2-hydroxy-2-methyl-3-oxobutanoic acid

Traditional IUPAC Name

2-acetyllactic acid

Chemical Formula

C₅H₈O₄

SMILES

[H]OC(=O)C(O[H])(C(=O)C([H])([H])[H])C([H])([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Beta-keto acid
Branched fatty acid
Hydroxy fatty acid
Short-chain keto acid
Methyl-branched fatty acid
Alpha-hydroxy acid
Fatty acyl
Acyloin
Beta-hydroxy ketone
Hydroxy acid
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-oxo monocarboxylic acid (CHEBI:16444 )
2-hydroxy monocarboxylic acid (CHEBI:16444 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	286 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.28	ChemAxon
logS	0.33	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.59 m³·mol⁻¹	ChemAxon
Polarizability	11.82 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

mitochondrion

Organoleptic Properties

Not Available

SMPDB Pathways

Pantothenate and CoA biosynthesis

PW002463

KEGG Pathways

Butanoate metabolism	ec00650
Pantothenate and CoA biosynthesis	ec00770

SMPDB Reactions

Not Available

KEGG Reactions

NADPH + hydron + 2-Acetolactate → NADP + (R)-2,3-Dihydroxy-isovalerate

Pyruvic acid + hydron → Carbon dioxide + 2-Acetolactate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0c1fe460a2ec8a1a255d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0303-9780000000-ed6c7b366835f2a4a9c0	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-001i-5900000000-a14af8bd96fdcce5e84f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015l-9400000000-53c1f10a4a9b63a25574	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-9000000000-03c96ef4ce31ab174fdd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9700000000-641c507686f1b0493bde	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-cd68c82882667330e329	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-9000000000-f0530bd3c4f32baa697c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9300000000-0c998add67e750d36bc4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9200000000-3e8a380405cb5b02d1d7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-aeeb164d9240ff735bc5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ke-9200000000-c8b983df55a14da2898a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-79267be0bc618dc8018f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cd1679ff8fbd31e9b90f	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:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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
Cullin, C., Baudin-Baillieu, A., Guillemet, E., Ozier-Kalogeropoulos, O. (1996). "Functional analysis of YCL09C: evidence for a role as the regulatory subunit of acetolactate synthase." Yeast 12:1511-1518.8972574

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16444
HMDB ID	HMDB06833
Pubchem Compound ID	22
Kegg ID	C00900
ChemSpider ID	21
FOODB ID	FDB024109
Wikipedia ID	Acetolactic acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. Ketol-acid reductoisomerase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: (R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:: ILV5
Uniprot ID:: P06168
Molecular weight:: 44368.10156

Reactions

(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) → (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) → (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.

Protein Details

2. Acetolactate synthase catalytic subunit, mitochondrial

General function:: Involved in magnesium ion binding
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ILV2
Uniprot ID:: P07342
Molecular weight:: 74936.29688

Reactions

2 pyruvate → 2-acetolactate + CO(2).

Structure for #<Compound:0x9671104c>

Enzymes

Reactions

Reactions