P. aeruginosa Metabolome Database: (S)-2-Acetolactate (PAMDB000697)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000697

Identification

Name:

(S)-2-Acetolactate

Description:

(S)-2-Acetolactate is an intermediate in the biosynthesis of valine, leucine and isoleucine (KEGG ID C06010 ). It is the sixth to last step in the synthesis of protein and is converted from 2-hydroxy-3-methyl-2-oxobutanoate via the enzyme acetolactate synthase [EC:2.2.1.6]. It is then converted to 3-hydroxy-3-methyl-2-oxobutanoate via the enzyme ketol-acid reductoisomerase [EC:1.1.1.86].

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(S)-2-Acetolactic acid
(S)-2-Hydroxy-2-methyl-3-oxobutanoate
(S)-2-Hydroxy-2-methyl-3-oxobutanoic acid
2-Ac

Chemical Formula:

C₅H₈O₄

Average Molecular Weight:

132.1146

Monoisotopic Molecular Weight:

132.042258744

InChI Key:

NMDWGEGFJUBKLB-YFKPBYRVSA-N

InChI:

InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

acetolactic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-acetyllactic acid (CHEBI:18409 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	286.0 mg/mL	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	11.81 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:

Hydrogen ion + 2 Pyruvic acid > (S)-2-Acetolactate + Carbon dioxide
(R)-2,3-Dihydroxy-isovalerate + NADP <> (S)-2-Acetolactate + Hydrogen ion + NADPH
(S)-2-Acetolactate + Carbon dioxide <>2 Pyruvic acid
(S)-2-Acetolactate <> 3-Hydroxy-3-methyl-2-oxobutanoic acid
(R)-2,3-Dihydroxy-isovalerate + NADP > (S)-2-Acetolactate + NADPH
(S)-2-Acetolactate + Hydrogen ion + NADPH + NADPH > NADP + (R)-2,3-Dihydroxy-isovalerate

Pathways:

C5-Branched dibasic acid metabolism pae00660
Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770
Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-5900000000-a14af8bd96fdcce5e84f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015l-9400000000-53c1f10a4a9b63a25574	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-9000000000-03c96ef4ce31ab174fdd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9700000000-641c507686f1b0493bde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-cd68c82882667330e329	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-9000000000-f0530bd3c4f32baa697c	View in MoNA

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
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	18409
HMDB ID	HMDB06855
Pubchem Compound ID	440878
Kegg ID	C06010
ChemSpider ID	389710
Wikipedia ID	Not Available
BioCyc ID	Not Available

(S)-2-Acetolactate (PAMDB000697)

Structure for (S)-2-Acetolactate (PAMDB000697)