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Showing metabocard for alpha-Hydroxyisobutyric acid (HMDB0000729)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:52 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000729 (alpha-Hydroxyisobutyric acid)

  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
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3D MOL for HMDB0000729 (alpha-Hydroxyisobutyric acid)

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0000729 (alpha-Hydroxyisobutyric acid)

  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000729

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.872501504091092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylpropanoic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-0.039063632000000056

> <ALOGPS_LOGS>
0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.40275140597527

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.948421773706818

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7355605250234243

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.5531

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetonate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000729 (alpha-Hydroxyisobutyric acid)

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0000729 (alpha-Hydroxyisobutyric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -3.255   1.390   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.588  -0.920   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.951  -2.123   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.897  -2.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.265  -0.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.582  -0.148   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.916  -0.918   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    7                                                            
CONECT    4    7                                                            
CONECT    5    7    1    2                                                  
CONECT    6    7                                                            
CONECT    7    6    4    5    3                                             
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0000729 (alpha-Hydroxyisobutyric acid)

COMPND    HMDB0000729
HETATM    1  C1  UNL     1      -0.254   1.443   0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.176  -0.022   0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.988  -0.777  -0.685  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.759  -0.156   1.633  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.195  -0.544   0.356  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.672  -1.020   1.405  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.944  -0.508  -0.796  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.246   2.096   0.916  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.539   1.731  -0.721  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.215   1.663  -0.513  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.760  -0.273  -1.656  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.745  -1.851  -0.709  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.056  -0.583  -0.437  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.009  -1.110   1.731  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.856  -0.090  -0.889  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0000729 (alpha-Hydroxyisobutyric acid)

CC(C)(O)C(O)=O
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INCHI for HMDB0000729 (alpha-Hydroxyisobutyric acid)

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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 locationSource
ProcessNot Available
Role
Environmental roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling Point212.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.36HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
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
MarkerDB IDMDB00000238
Good Scents IDrw1176881
References
Synthesis ReferenceVogl, 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
  1. 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 ]
  2. 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 ]
  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

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