ECMDB: 2-Aceto-2-hydroxy-butyrate (ECMDB04001) (M2MDB000549)

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

Proteins (1638)

Record Information

Version

2.0

Creation Date

2012-05-31 14:01:40 -0600

Update Date

2015-06-03 15:54:35 -0600

Secondary Accession Numbers

ECMDB04001

Identification

Name:

2-Aceto-2-hydroxy-butyrate

Description

(S)-2-Aceto-2-hydroxybutanoic acid is an intermediate in branched chain amino acid metabolism. It is converted from 2-oxobutanoate or 2-hydoxyethyl ThPP via acetolactate synthase.

Structure

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

Synonyms:

α-aceto-α-hydroxybutyrate
α-aceto-α-hydroxybutyric acid
(2S)-2-ethyl-2-hydroxy-3-oxobutanoate
(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
(S)-2-Aceto-2-hydroxybutanoate
(S)-2-Aceto-2-hydroxybutanoic acid
(S)-2-Hydroxy-2-ethyl-3-oxobutanoate
(S)-2-Hydroxy-2-ethyl-3-oxobutanoic acid
2-aceto-2-hydroxy-butyrate
2-Aceto-2-hydroxy-butyric acid
a-aceto-a-Hydroxybutyrate
a-aceto-a-Hydroxybutyric acid
Acetohydroxybutanoate
Acetohydroxybutanoic acid
Acetohydroxybutyrate
Acetohydroxybutyric acid
Alpha-Aceto-alpha-hydroxybutyrate
Alpha-Aceto-alpha-hydroxybutyric acid
α-aceto-α-Hydroxybutyrate
α-aceto-α-Hydroxybutyric acid

Chemical Formula:

C₆H₁₀O₄

Weight:

Average: 146.1412
Monoisotopic: 146.057908808

InChI Key:

VUQLHQFKACOHNZ-LURJTMIESA-N

InChI:

InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1

CAS number:

3142-65-2

IUPAC Name:

(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid

Traditional IUPAC Name:

(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid

SMILES:

CC[C@](O)(C(C)=O)C(O)=O

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
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

hydroxy monocarboxylic acid (CHEBI:27681 )
3-oxo monocarboxylic acid (CHEBI:27681 )
Hydroxy fatty acids (LMFA01050383 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	259 g/L	ALOGPS
logP	-0.58	ALOGPS
logP	0.24	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	-4.7	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	3	ChemAxon
Refractivity	33.11 m³·mol⁻¹	ChemAxon
Polarizability	13.72 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:

isoleucine biosynthesis

PW000818

KEGG Pathways:

Valine, leucine and isoleucine biosynthesis ec00290

EcoCyc Pathways:

isoleucine biosynthesis I (from threonine) ILEUSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-4a32387e4d1a3c2518e2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-9260000000-03d854f5c6e2c1cd66cc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1900000000-58139948a2d318b20cd3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-7900000000-5d95d041962e4d0c29c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9400000000-54a124cdee1ab9c9f382	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-c26fd82bd80ef12ed78a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9500000000-79a2c717c39914d90709	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-14cfb3f09136a8d1b1fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-0900000000-e31b2e7070d5d06bb420	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kam-9200000000-8e85855717b408d3368e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-0a3fed2352239366e095	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kal-9600000000-fd5ff61bfd773a3d7ff1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-775b97d756977d989ad0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-9000000000-287791e86291cbac2749	View in MoNA
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
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	27681
HMDB ID	HMDB0006900
Pubchem Compound ID	8279
Kegg ID	C06006
ChemSpider ID	389708
Wikipedia ID	Not Available
BioCyc ID	2-ACETO-2-HYDROXY-BUTYRATE
EcoCyc ID	2-ACETO-2-HYDROXY-BUTYRATE

Enzymes

Protein Details

1. Acetolactate synthase isozyme 3 large subunit

General function:: Involved in magnesium ion binding
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ilvI
Uniprot ID:: P00893
Molecular weight:: 62984

Reactions

2 pyruvate = 2-acetolactate + CO(2).

Protein Details

2. Acetolactate synthase isozyme 3 small subunit

General function:: Involved in acetolactate synthase activity
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ilvH
Uniprot ID:: P00894
Molecular weight:: 17977

Reactions

2 pyruvate = 2-acetolactate + CO(2).

Protein Details

3. Ketol-acid reductoisomerase

General function:: Involved in oxidation-reduction process
Specific function:: (R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:: ilvC
Uniprot ID:: P05793
Molecular weight:: 54069

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

4. Acetolactate synthase isozyme 1 large subunit

General function:: Involved in magnesium ion binding
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ilvB
Uniprot ID:: P08142
Molecular weight:: 60440

Reactions

2 pyruvate = 2-acetolactate + CO(2).

Protein Details

5. Acetolactate synthase isozyme 1 small subunit

General function:: Involved in amino acid binding
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ilvN
Uniprot ID:: P0ADF8
Molecular weight:: 11106

Reactions

2 pyruvate = 2-acetolactate + CO(2).

Protein Details

6. Acetolactate synthase isozyme 2 small subunit

General function:: Involved in acetolactate synthase activity
Specific function:: 2 pyruvate = 2-acetolactate + CO(2)
Gene Name:: ilvM
Uniprot ID:: P0ADG1
Molecular weight:: 9703

Reactions

2 pyruvate = 2-acetolactate + CO(2).

2-Aceto-2-hydroxy-butyrate (ECMDB04001) (M2MDB000549)

Structure for #<Compound:0xa7531f2c>

Enzymes

Reactions

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