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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-08-12 16:59:57 UTC

Update Date

2023-02-21 17:17:21 UTC

HMDB ID

HMDB0006833

Secondary Accession Numbers

HMDB06833

Metabolite Identification

Common Name

2-Acetolactate

Description

2-Acetolactate is involved in the butanoate metabolism and pantothenate and CoA biosynthesis pathways. In the butanoate metabolism pathway, 2-Acetolactate is created from 2-(alpha-Hydroxyethyl)thiamine diphosphate by acetolactate synthase [EC:2.2.1.6]. 2-Acetolactate is then converted to (R)-Acetoin by acetolactate decarboxylase [EC:4.1.1.5]. In the pantothenate and CoA pathway, 2-Acetolactate is irreversibly created from pyruvate by acetolactate synthase [EC:2.2.1.6]. 2-Acetolactate is then irreversibly converted to 2,3-Dihydroxy-3-methylbutanoate by ketol-acid reductoisomerase [EC:1.1.1.86].

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Acetolactic acid	Generator
2-Acetolactate	ChEBI

Chemical Formula

C₅H₈O₄

Average Molecular Weight

132.1146

Monoisotopic Molecular Weight

132.042258744

IUPAC Name

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

Traditional Name

2-acetyllactic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C(C)(O)C(O)=O

InChI Identifier

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

InChI Key

NMDWGEGFJUBKLB-UHFFFAOYSA-N

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0006833)

Exogenous

Food

Food (HMDB: HMDB0006833)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006833)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0006833)

Biochemical pathway

Metabolic pathway

2-Oxopent-4-enoate Metabolism (PathBank: SMP0001904)
2-Oxopent-4-enoate Metabolism 2 (PathBank: SMP0002049)

Role

Biological role

Energy source (HMDB: HMDB0006833)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006833)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.016	31661259
DarkChem	[M-H]-	122.916	31661259
DeepCCS	[M+H]+	123.215	30932474
DeepCCS	[M-H]-	120.038	30932474
DeepCCS	[M-2H]-	156.824	30932474
DeepCCS	[M+Na]+	131.804	30932474
AllCCS	[M+H]+	130.7	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	134.5	32859911
AllCCS	[M+Na]+	135.7	32859911
AllCCS	[M-H]-	124.2	32859911
AllCCS	[M+Na-2H]-	126.9	32859911
AllCCS	[M+HCOO]-	130.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetolactate	CC(=O)C(C)(O)C(O)=O	2102.8	Standard polar	33892256
2-Acetolactate	CC(=O)C(C)(O)C(O)=O	992.8	Standard non polar	33892256
2-Acetolactate	CC(=O)C(C)(O)C(O)=O	1113.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Acetolactate,1TMS,isomer #1	CC(=O)C(C)(O[Si](C)(C)C)C(=O)O	1211.7	Semi standard non polar	33892256
2-Acetolactate,1TMS,isomer #2	CC(=O)C(C)(O)C(=O)O[Si](C)(C)C	1109.3	Semi standard non polar	33892256
2-Acetolactate,1TMS,isomer #3	C=C(O[Si](C)(C)C)C(C)(O)C(=O)O	1183.6	Semi standard non polar	33892256
2-Acetolactate,2TMS,isomer #1	CC(=O)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1241.3	Semi standard non polar	33892256
2-Acetolactate,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O	1305.4	Semi standard non polar	33892256
2-Acetolactate,2TMS,isomer #3	C=C(O[Si](C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C	1215.9	Semi standard non polar	33892256
2-Acetolactate,3TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1354.7	Semi standard non polar	33892256
2-Acetolactate,3TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1357.5	Standard non polar	33892256
2-Acetolactate,3TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1341.1	Standard polar	33892256
2-Acetolactate,1TBDMS,isomer #1	CC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O	1444.9	Semi standard non polar	33892256
2-Acetolactate,1TBDMS,isomer #2	CC(=O)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C	1354.7	Semi standard non polar	33892256
2-Acetolactate,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O	1414.7	Semi standard non polar	33892256
2-Acetolactate,2TBDMS,isomer #1	CC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1690.0	Semi standard non polar	33892256
2-Acetolactate,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O	1749.4	Semi standard non polar	33892256
2-Acetolactate,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)O[Si](C)(C)C(C)(C)C	1692.1	Semi standard non polar	33892256
2-Acetolactate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2005.9	Semi standard non polar	33892256
2-Acetolactate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1994.3	Standard non polar	33892256
2-Acetolactate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1798.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetolactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0c1fe460a2ec8a1a255d	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetolactate GC-MS (2 TMS) - 70eV, Positive	splash10-0303-9780000000-ed6c7b366835f2a4a9c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetolactate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetolactate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 10V, Positive-QTOF	splash10-001i-5900000000-a14af8bd96fdcce5e84f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 20V, Positive-QTOF	splash10-015l-9400000000-53c1f10a4a9b63a25574	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 40V, Positive-QTOF	splash10-01b9-9000000000-03c96ef4ce31ab174fdd	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 10V, Negative-QTOF	splash10-0019-9700000000-641c507686f1b0493bde	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 20V, Negative-QTOF	splash10-000i-9000000000-cd68c82882667330e329	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 40V, Negative-QTOF	splash10-0079-9000000000-f0530bd3c4f32baa697c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 10V, Negative-QTOF	splash10-000i-9300000000-0c998add67e750d36bc4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 20V, Negative-QTOF	splash10-000i-9200000000-3e8a380405cb5b02d1d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 40V, Negative-QTOF	splash10-0006-9000000000-aeeb164d9240ff735bc5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 10V, Positive-QTOF	splash10-00ke-9200000000-c8b983df55a14da2898a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 20V, Positive-QTOF	splash10-0006-9000000000-79267be0bc618dc8018f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetolactate 40V, Positive-QTOF	splash10-0006-9000000000-cd1679ff8fbd31e9b90f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024109

KNApSAcK ID

C00019658

Chemspider ID

KEGG Compound ID

C00900

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetolactic acid

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

16444

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetolactate synthase-like protein

General function:: Involved in magnesium ion binding
Specific function:: Not Available
Gene Name:: ILVBL
Uniprot ID:: A1L0T0
Molecular weight:: 67867.2

Showing metabocard for 2-Acetolactate (HMDB0006833)

MOL for HMDB0006833 (2-Acetolactate)

3D MOL for HMDB0006833 (2-Acetolactate)

3D SDF for HMDB0006833 (2-Acetolactate)

3D-SDF for HMDB0006833 (2-Acetolactate)

PDB for HMDB0006833 (2-Acetolactate)

3D PDB for HMDB0006833 (2-Acetolactate)

SMILES for HMDB0006833 (2-Acetolactate)

INCHI for HMDB0006833 (2-Acetolactate)

Structure for HMDB0006833 (2-Acetolactate)

3D Structure for HMDB0006833 (2-Acetolactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes