MiMeDB: Showing metabocard for 3-Hydroxy-3-methyl-2-oxobutanoic acid (MMDBc0030000)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:50:08 UTC

Update Date

2022-08-31 17:38:33 UTC

Metabolite ID

MMDBc0030000

Metabolite Identification

Common Name

3-Hydroxy-3-methyl-2-oxobutanoic acid

Description

3-hydroxy-3-methyl-2-oxobutanoic acid belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)Œ±-Acetolactic acid (Œ±-acetolactate) is a precursor in the biosynthesis of the branched chain amino acids valine and leucine. Œ±-Acetolactic acid is produced from two molecules of pyruvic acid by acetolactate synthase. Œ±-Acetolactic acid can also be decarboxylated by alpha-acetolactate decarboxylase to produce acetoin. (WikiPedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-oxo-3-Hydroxyisovaleric acid	ChEBI
3-Hydroxy-3-methyl-2-oxobutanoate	ChEBI
2-oxo-3-Hydroxyisovalerate	Kegg
3-Hydroxy-3-methyl-2-oxobutanoic acid	Generator
3-Hydroxy-3-methyl-2-oxo-butanoate	Generator

Molecular Formula

C₅H₈O₄

Average Mass

132.1146

Monoisotopic Mass

132.042258744

IUPAC Name

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

Traditional Name

2-oxo-3-hydroxyisovaleric acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

DNOPJXBPONYBLB-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:17667 )
Branched fatty acids (C04181 )
Branched fatty acids (LMFA01020277 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	144 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	0.25	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-3.5	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	28.9 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-c3161384e1488957714d	2018-04-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0900000000-dccd800cefa7d4bdae84	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9300000000-aff677d2cd37168fb67c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-32ca0d880db7bf46c327	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9600000000-96fbea05d7278545b47b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-9500000000-61d5bee615e1e017f036	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-9000000000-d955d55b4d55200cf346	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019185	(S)-2-Acetolactate	3-Hydroxy-3-methyl-2-oxobutanoic acid	Ketol-acid reductoisomerase (NADP(+))	Isomerization	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0154759

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04181

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440248

PDB ID

Not Available

ChEBI ID

17667

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 3-Hydroxy-3-methyl-2-oxobutanoic acid (MMDBc0030000)

MOL for #<Metabolite:0x00007fa50a9be680>

3D MOL for #<Metabolite:0x00007fa50a9be680>

3D SDF for #<Metabolite:0x00007fa50a9be680>

3D-SDF for #<Metabolite:0x00007fa50a9be680>

PDB for #<Metabolite:0x00007fa50a9be680>

3D PDB for #<Metabolite:0x00007fa50a9be680>

SMILES for #<Metabolite:0x00007fa50a9be680>

INCHI for #<Metabolite:0x00007fa50a9be680>

Structure for #<Metabolite:0x00007fa50a9be680>

3D Structure for #<Metabolite:0x00007fa50a9be680>