Human Metabolome Database: Showing metabocard for alpha-Hydroxyisobutyric acid (HMDB0000729)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2019-07-23 05:44:26 UTC

HMDB ID

HMDB0000729

Secondary Accession Numbers

HMDB00729

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 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Lung cancer

Disposition

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

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
Water Solubility	378 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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
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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	8.2 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	7.0 (0.0-9.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	9.00 +/- 2.95 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	2.9 (1.3-4.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	4.4-7.4 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	7.821 +/- 3.811 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	3.80 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.1 (0.1-3.8) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	6.2 (3.8-14.1) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	5.5 (2.9-10.3) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	<50 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	7.9 (3.7-19.5) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	0.1 (0.1-8.2) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.4-7.6 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	3.8 (1.7-5.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	13.322 +/- 5.638 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Lung cancer	25961003	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	9.37 +/- 5.223 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	5.0 (0.0-8.0) umol/mmol creatinine	Not Specified	Both	Lung cancer	18953024	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	11.83 +/- 4.351 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	12.057 +/- 6.013 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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 ] 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 ] 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
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 ] 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
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

114500 (Colorectal cancer)
211980 (Lung Cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

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)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

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 acid	details
alpha-Hydroxyisobutyric acid → 3,4,5-trihydroxy-6-[(2-hydroxy-2-methylpropanoyl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for alpha-Hydroxyisobutyric acid (HMDB0000729)

Structure for HMDB0000729 (alpha-Hydroxyisobutyric acid)

Enzymes

Reactions