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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:32 UTC
HMDB IDHMDB0000729
Secondary Accession Numbers
  • HMDB00729
Metabolite Identification
Common Namealpha-Hydroxyisobutyric acid
Descriptionalpha-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 metabolized to t-butyl alcohol (TBA) and formaldehyde and oxidized to 2-methyl-1,2-propanediol and alpha-hydroxyisobutyric acid. alpha-Hydroxyisobutyric acid has been used as an aerial bactericide.
Structure
Data?1582752152
Synonyms
ValueSource
2-Hydroxy-2-methylpropionic acidChEBI
2-Hydroxy-2-methylpropionsaeureChEBI
2-Methyl-2-hydroxypropanoic acidChEBI
2-Methyl-2-hydroxypropionsaeureChEBI
2-Methyllactic acidChEBI
Acetonic acidChEBI
Acide 2-hydroxy-2-methylpropanoiqueChEBI
Acido 2-hidroxi-2-metilpropionicoChEBI
alpha-Hydroxy-alpha-methylpropanoic acidChEBI
alpha-Hydroxy-alpha-methylpropionic acidChEBI
alpha-Hydroxyisobutanoic acidChEBI
HIBAChEBI
Hydroxydimethylacetic acidChEBI
2-Hydroxy-2-methylpropionateGenerator
2-Methyl-2-hydroxypropanoateGenerator
2-MethyllactateGenerator
AcetonateGenerator
a-Hydroxy-a-methylpropanoateGenerator
a-Hydroxy-a-methylpropanoic acidGenerator
alpha-Hydroxy-alpha-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoic acidGenerator
a-Hydroxy-a-methylpropionateGenerator
a-Hydroxy-a-methylpropionic acidGenerator
alpha-Hydroxy-alpha-methylpropionateGenerator
Α-hydroxy-α-methylpropionateGenerator
Α-hydroxy-α-methylpropionic acidGenerator
a-HydroxyisobutanoateGenerator
a-Hydroxyisobutanoic acidGenerator
alpha-HydroxyisobutanoateGenerator
Α-hydroxyisobutanoateGenerator
Α-hydroxyisobutanoic acidGenerator
HydroxydimethylacetateGenerator
a-HydroxyisobutyrateGenerator
a-Hydroxyisobutyric acidGenerator
alpha-HydroxyisobutyrateGenerator
Α-hydroxyisobutyrateGenerator
Α-hydroxyisobutyric acidGenerator
a-Hydroxy-isobutyrateHMDB
a-Hydroxy-isobutyric acidHMDB
alpha-Hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyric acidHMDB
(CH3)2cohcoohHMDB
2-Hydroxy-2-methylpropanoateHMDB
2-Hydroxy-2-methylpropanoic acidHMDB
2-HydroxyisobutyrateHMDB
2-Hydroxyisobutyric acidHMDB
a-HIBHMDB
alpha-HIBHMDB
HydroxyisobutyrateHMDB
L-2-MethyllactateHMDB
L-2-Methyllactic acidHMDB
2-Hydroxyisobutyric acid, lead saltHMDB
Lead 2-hydroxyisobutyric acidHMDB
alpha-Hydroxyisobutyric acidChEBI
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name2-hydroxy-2-methylpropanoic acid
Traditional Nameacetonate
CAS Registry Number594-61-6
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 KeyBWLBGMIXKSTLSX-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.36HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility378 g/LALOGPS
logP-0.37ALOGPS
logP-0.039ChemAxon
logS0.56ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.55 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-8900000000-2d2298731d2c1ce975ffSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-bb87a50521380a4f04c0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00e9-8900000000-2d2298731d2c1ce975ffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-af78bdeb830f08b3a6a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00su-9610000000-cea13166d0c9b277d7d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-8900000000-b51c12e744025b833f31Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9100000000-0d72fcffff267d7bc980Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-09121cf499d55d5656acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0pb9-9600000000-3394a5ec4ff4ff576fcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-5fc3362d72c467fb6197Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-052f-9000000000-3de5183bd97ccc5072c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d524fab140880c782425Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-591fd3d7ad484dd6f1ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0udi-0900000000-69f23830b20d34978bedSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-09121cf499d55d5656acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9600000000-3394a5ec4ff4ff576fcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-5fc3362d72c467fb6197Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9000000000-3de5183bd97ccc5072c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d524fab140880c782425Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-591fd3d7ad484dd6f1ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-69f23830b20d34978bedSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4l-9000000000-bb87a50521380a4f04c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-1aadb4e9ee70b665d435Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-1aadb4e9ee70b665d435Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-7f058188704b24bc8ceeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-40bbfa4d36a4c19902c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-237ae993c0cc1090dd96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-8900000000-f40f4783e4b817b45a70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-28ad10690e6680bd4046Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.0 (0.0-9.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified9.00 +/- 2.95 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.9 (1.3-4.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.4-7.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified7.821 +/- 3.811 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.80 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.1-3.8) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified6.2 (3.8-14.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified5.5 (2.9-10.3) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified<50 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified7.9 (3.7-19.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.1-8.2) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.4-7.6 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.8 (1.7-5.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.322 +/- 5.638 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Lung cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified9.37 +/- 5.223 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.0 (0.0-8.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified11.83 +/- 4.351 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified12.057 +/- 6.013 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
  2. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022207
KNApSAcK IDNot Available
Chemspider ID11181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3750
PubChem Compound11671
PDB IDNot Available
ChEBI ID50129
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceVogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Benson JM, Barr EB, Krone JR: MTBE inhaled alone and in combination with gasoline vapor: uptake, distribution, metabolism, and excretion in rats. Res Rep Health Eff Inst. 2001 May;(102):73-94; discussion 95-109. [PubMed:11504149 ]
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Isobutene (CAS No. 115-11-7) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1998 Dec;487:1-230. [PubMed:12563344 ]
  4. Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J: Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. [PubMed:7133811 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
alpha-Hydroxyisobutyric acid → 6-(1-carboxy-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
alpha-Hydroxyisobutyric acid → 3,4,5-trihydroxy-6-[(2-hydroxy-2-methylpropanoyl)oxy]oxane-2-carboxylic aciddetails