Livestock Metabolome Database: Showing metabocard for 2-Hydroxy-3-methylbutyric acid (LMDB00151)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:28 UTC

Update Date

2016-07-20 21:03:29 UTC

Lmdb

LMDB00151

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Hydroxy-3-methylbutyric acid

Description

2-Hydroxy-3-methylbutyric acid (also known as 2-Hydroxyisovaleric acid) is a metabolite found in the urine of patients with Phenylketonuria (PMID 7978272 ), Methylmalonic acidemia, Propionic acidemia, 3-Ketothiolase deficiency, Isovaleric acidemia, 3-Methylcrotonylglycemia, 3-Hydroxy-3-methylglutaric acidemia, Multiple carboxylase deficiency, Glutaric aciduria, Ornithine transcarbamylase deficiency, glyceroluria, Tyrosinemia type 1, Galactosemia, and Maple syrup urine disease (PMID 11048741 ). 2-hydroxyisovaleric acid has been identified in the urine of patients with lactic and ketoacidosis (PMID: 884872 ). It has also been identified in the urine of severely asphyxiated babies (PMID: 1610944 ). 2-hydroxyisovaleric acid originates mainly from ketogenesis and from the metabolism of valine, leucine and isoleucine (PMID: 6434570 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxyisopentanoic acid	ChEBI
2-Hydroxyisovaleric acid	ChEBI
3-Methyl-2-hydroxybutyric acid	ChEBI
alpha-Hydroxyisovaleric acid	ChEBI
2-Hydroxyisopentanoate	Generator
2-Hydroxyisovalerate	Generator
3-Methyl-2-hydroxybutyrate	Generator
a-Hydroxyisovalerate	Generator
a-Hydroxyisovaleric acid	Generator
alpha-Hydroxyisovalerate	Generator
Α-hydroxyisovalerate	Generator
Α-hydroxyisovaleric acid	Generator
2-Hydroxy-3-methylbutyrate	Generator
2-Hydroxy-3-methyl-butyric acid	HMDB
2-Hydroxy-3-methylbutanoate	HMDB
2-Hydroxy-3-methylbutanoic acid	HMDB
2-Oxyisovalerate	HMDB
2-Oxyisovaleric acid	HMDB
DL-2-Hydroxy-3-methylbutanoate	HMDB
DL-2-Hydroxy-3-methylbutanoic acid	HMDB
DL-2-Hydroxyisovalerate	HMDB
DL-2-Hydroxyisovaleric acid	HMDB
DL-a-Hydroxyisovalerate	HMDB
DL-a-Hydroxyisovaleric acid	HMDB
DL-alpha-Hydroxyisovalerate	HMDB
DL-alpha-Hydroxyisovaleric acid	HMDB
2-Hydroxyisovaleric acid, monosodium salt, (S)-isomer	HMDB
2-Hydroxyisovaleric acid, (S)-isomer	HMDB
2-Hydroxyisovaleric acid, calcium (2:1) salt	HMDB
2-Hydroxyisovaleric acid, (R)-isomer	HMDB

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

IUPAC Name

2-hydroxy-3-methylbutanoic acid

Traditional Name

2-hydroxyisovaleric acid

CAS Registry Number

4026-18-0

SMILES

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

InChI Identifier

InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)

InChI Key

NGEWQZIDQIYUNV-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Alpha-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy monocarboxylic acid (CHEBI:60645 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.1	ALOGPS
logP	0.42	ChemAxon
logS	0.26	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	27.84 m³·mol⁻¹	ChemAxon
Polarizability	11.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9100000000-3ceb85540106a01209a9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g1-9520000000-27e47b254facef447ecf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-01b9-9800000000-34c80f5b3cfe512db815	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-006t-9100000000-62b5dd0328186489f167	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00kb-9400000000-4b607be60b20b11a9328	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00di-9000000000-053084615922d2811fc0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-9000000000-c74232c34d7c991de0c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-052f-9000000000-1837dbe9ec7e7648abac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0gbc-9400000000-3dae3f739ba9de64475a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gi0-6900000000-9c5d211acf2118d6a136	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9100000000-fd55205401dd434cfdcc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-9000000000-44a71cd407c65a176f7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-6900000000-977b23edb76b18575dc2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-9400000000-a265e0ef4d3a3366c0be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-a258a01f539f2e2cd1e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-9100000000-4440e0dd7c3edf6166ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-848921fdd36001ccc2ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ec34045be03977dd8e79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-d5f27e5fc2f84d237f6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-7900000000-d8e0dd0fbaecb6b1909e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a096d70c21dd426764cb	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000407

FooDB ID

FDB022023

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5396

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

90190

ChEBI ID

60645

PubChem Compound ID

99823

Kegg Compound ID

Not Available

YMDB ID

YMDB01318

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magni F, Arnoldi L, Galati G, Galli Kienle M: Simultaneous determination of plasma levels of alpha-ketoisocaproic acid and leucine and evaluation of alpha-[1-13C]ketoisocaproic acid and [1-13C]leucine enrichment by gas chromatography-mass spectrometry. Anal Biochem. 1994 Aug 1;220(2):308-14. [7978272 ]
Ohie T, Fu X, Iga M, Kimura M, Yamaguchi S: Gas chromatography-mass spectrometry with tert.-butyldimethylsilyl derivation: use of the simplified sample preparations and the automated data system to screen for organic acidemias. J Chromatogr B Biomed Sci Appl. 2000 Sep 1;746(1):63-73. [11048741 ]
Landaas S, Jakobs C: The occurrence of 2-hydroxyisovaleric acid in patients with lactic acidosis and ketoacidosis. Clin Chim Acta. 1977 Aug 1;78(3):489-93. [884872 ]
Walker V, Mills GA: Effects of birth asphyxia on urinary organic acid excretion. Biol Neonate. 1992;61(3):162-72. [1610944 ]
Liebich HM, Forst C: Hydroxycarboxylic and oxocarboxylic acids in urine: products from branched-chain amino acid degradation and from ketogenesis. J Chromatogr. 1984 Aug 10;309(2):225-42. [6434570 ]

Showing metabocard for 2-Hydroxy-3-methylbutyric acid (LMDB00151)

Structure for LMDB00151 (2-Hydroxy-3-methylbutyric acid)