Bovine Metabolome Database: Showing metabocard for Alpha-Hydroxyisobutyric acid (BMDB0000729)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:36 UTC

Update Date

2020-05-11 20:37:46 UTC

BMDB ID

BMDB0000729

Secondary Accession Numbers

BMDB00729

Metabolite Identification

Common Name

Alpha-Hydroxyisobutyric acid

Description

alpha-Hydroxyisobutyric acid, also known as a-hydroxyisobutyrate or 2-methyllactic acid, 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. Based on a literature review a significant number of articles have been published on alpha-Hydroxyisobutyric acid.

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

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	82.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.36	HANSCH,C ET AL. (1995)

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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00e9-8900000000-2d2298731d2c1ce975ff	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-bb87a50521380a4f04c0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00e9-8900000000-2d2298731d2c1ce975ff	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-af78bdeb830f08b3a6a6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00su-9610000000-cea13166d0c9b277d7d8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-8900000000-b51c12e744025b833f31	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9100000000-0d72fcffff267d7bc980	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4l-9000000000-bb87a50521380a4f04c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-09121cf499d55d5656ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d524fab140880c782425	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-1aadb4e9ee70b665d435	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0udi-0900000000-69f23830b20d34978bed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-09121cf499d55d5656ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d524fab140880c782425	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-69f23830b20d34978bed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-8900000000-f40f4783e4b817b45a70	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-28ad10690e6680bd4046	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0a3b71647acebd936a7e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-7f058188704b24bc8cee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-40bbfa4d36a4c19902c0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-237ae993c0cc1090dd96	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000729

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022207

KNApSAcK ID

Not Available

Chemspider ID

11181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3750

PubChem Compound

11671

PDB ID

Not Available

ChEBI ID

50129

References

Synthesis Reference

Vogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Alpha-Hydroxyisobutyric acid (BMDB0000729)

Structure for BMDB0000729 (Alpha-Hydroxyisobutyric acid)