Livestock Metabolome Database: Showing metabocard for Alpha-Hydroxyisobutyric acid (LMDB00231)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:15 UTC

Update Date

2016-07-20 21:03:44 UTC

Lmdb

LMDB00231

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alpha-Hydroxyisobutyric acid

Description

Alpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-2-methylpropionic acid	ChEBI
2-Hydroxy-2-methylpropionsaeure	ChEBI
2-Methyl-2-hydroxypropanoic acid	ChEBI
2-Methyl-2-hydroxypropionsaeure	ChEBI
2-Methyllactic acid	ChEBI
Acetonic acid	ChEBI
Acide 2-hydroxy-2-methylpropanoique	ChEBI
Acido 2-hidroxi-2-metilpropionico	ChEBI
alpha-Hydroxy-alpha-methylpropanoic acid	ChEBI
alpha-Hydroxy-alpha-methylpropionic acid	ChEBI
alpha-Hydroxyisobutanoic acid	ChEBI
HIBA	ChEBI
Hydroxydimethylacetic acid	ChEBI
2-Hydroxy-2-methylpropionate	Generator
2-Methyl-2-hydroxypropanoate	Generator
2-Methyllactate	Generator
Acetonate	Generator
a-Hydroxy-a-methylpropanoate	Generator
a-Hydroxy-a-methylpropanoic acid	Generator
alpha-Hydroxy-alpha-methylpropanoate	Generator
Α-hydroxy-α-methylpropanoate	Generator
Α-hydroxy-α-methylpropanoic acid	Generator
a-Hydroxy-a-methylpropionate	Generator
a-Hydroxy-a-methylpropionic acid	Generator
alpha-Hydroxy-alpha-methylpropionate	Generator
Α-hydroxy-α-methylpropionate	Generator
Α-hydroxy-α-methylpropionic acid	Generator
a-Hydroxyisobutanoate	Generator
a-Hydroxyisobutanoic acid	Generator
alpha-Hydroxyisobutanoate	Generator
Α-hydroxyisobutanoate	Generator
Α-hydroxyisobutanoic acid	Generator
Hydroxydimethylacetate	Generator
a-Hydroxyisobutyrate	Generator
a-Hydroxyisobutyric acid	Generator
alpha-Hydroxyisobutyrate	Generator
Α-hydroxyisobutyrate	Generator
Α-hydroxyisobutyric acid	Generator
a-Hydroxy-isobutyrate	HMDB
a-Hydroxy-isobutyric acid	HMDB
alpha-Hydroxy-isobutyrate	HMDB
Α-hydroxy-isobutyrate	HMDB
Α-hydroxy-isobutyric acid	HMDB
(CH3)2cohcooh	HMDB
2-Hydroxy-2-methylpropanoate	HMDB
2-Hydroxy-2-methylpropanoic acid	HMDB
2-Hydroxyisobutyrate	HMDB
2-Hydroxyisobutyric acid	HMDB
a-HIB	HMDB
alpha-HIB	HMDB
Hydroxyisobutyrate	HMDB
L-2-Methyllactate	HMDB
L-2-Methyllactic acid	HMDB
2-Hydroxyisobutyric acid, lead salt	HMDB
Lead 2-hydroxyisobutyric acid	HMDB
alpha-Hydroxyisobutyric acid	ChEBI

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

2-hydroxy-2-methylpropanoic acid

Traditional Name

acetonate

CAS Registry Number

594-61-6

SMILES

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

InChI Identifier

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

InChI Key

BWLBGMIXKSTLSX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy monocarboxylic acid (CHEBI:50129 )
Hydroxy fatty acids (LMFA01050417 )

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	-0.37	ALOGPS
logP	-0.039	ChemAxon
logS	0.56	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-3.7	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	1	ChemAxon
Refractivity	23.55 m³·mol⁻¹	ChemAxon
Polarizability	9.87 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00e9-8900000000-2d2298731d2c1ce975ff	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-bb87a50521380a4f04c0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00e9-8900000000-2d2298731d2c1ce975ff	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-af78bdeb830f08b3a6a6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00su-9610000000-cea13166d0c9b277d7d8	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)	splash10-0zfr-8900000000-b51c12e744025b833f31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9100000000-0d72fcffff267d7bc980	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4l-9000000000-bb87a50521380a4f04c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-09121cf499d55d5656ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d524fab140880c782425	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-1aadb4e9ee70b665d435	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0udi-0900000000-69f23830b20d34978bed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-09121cf499d55d5656ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d524fab140880c782425	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-69f23830b20d34978bed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-8900000000-f40f4783e4b817b45a70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-28ad10690e6680bd4046	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0a3b71647acebd936a7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-7f058188704b24bc8cee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-40bbfa4d36a4c19902c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-237ae993c0cc1090dd96	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000729

FooDB ID

FDB022207

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

3750

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

11181

ChEBI ID

50129

PubChem Compound ID

11671

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Alpha-Hydroxyisobutyric acid (LMDB00231)

Structure for LMDB00231 (Alpha-Hydroxyisobutyric acid)