MiMeDB: Showing metabocard for (S)-3-Hydroxyisobutyric acid (MMDBc0057091)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-09-24 20:43:31 UTC

Update Date

2022-08-30 22:57:22 UTC

Metabolite ID

MMDBc0057091

Metabolite Identification

Common Name

(S)-3-Hydroxyisobutyric acid

Description

Indolylacryloylglycine, also known as IAG or indoleacrylic glycine, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Indolylacryloylglycine (IAG) is a compound that is derived, in the same way as many other indole compounds, from tryptophan or indole compounds in the diet. Indolylacryloylglycine is a moderately basic compound (based on its pKa). Outside of the human body, Indolylacryloylglycine has been detected, but not quantified in, milk (cow). This could make indolylacryloylglycine a potential biomarker for the consumption of these foods. Indolylacryloylglycine is elevated in the urine of autistic children with gastrointestinal disturbances. It is likely a product of gut metabolism although the exact source is still unclear.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₄H₈O₃

Average Mass

104.1045

Monoisotopic Mass

104.047344122

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

26543-05-5

SMILES

Not Available

InChI Identifier

InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

DBXBTMSZEOQQDU-VKHMYHEASA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo_sapiens
MMDBp0192047	Peroxisomal bifunctional enzyme	Unknown	Q08426	Homo_sapiens
MMDBp0192048	Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial	Unknown	Q16836	Homo_sapiens
MMDBp0192062	3-hydroxyisobutyrate dehydrogenase, mitochondrial	Unknown	P31937	Homo_sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens
MMDBp0193982	3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Enzyme	Q6NVY1	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Diabetes mellitus type 2	Increased	Association	Human Blood	HMDB	2614280
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
3-Hydroxyisobutyric aciduria	Slight Decrease	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
3-Hydroxyisobutyric aciduria	Increased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	78	Human feces; Human pleural fluid plaque; Human dental plaque; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	163	Human feces; Human pleural fluid plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	131	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	14	Human feces; Human	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected but not Quantified								HMDB
Human	Detected and Quantified	38.0	5.0			Adult (>18 years old)	Both	Diabetes	HMDB	2614280
Human	Detected and Quantified			10	17.0	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human	Detected and Quantified			10.0	15.9	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human	Detected and Quantified	11		4.1	19	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human	Detected and Quantified	14.5		5.5	28.7	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human	Detected and Quantified	18.0 +/- 18.0		0	36	Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human	Detected and Quantified	20.0		4.0	48.0	Children (1-13 years old)	Both	Normal	HMDB	8412012
Human	Detected and Quantified	21.0	2.0			Adult (>18 years old)	Both	Normal	HMDB	2614280
Human	Detected and Quantified	25.4		10.2	33.5	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human	Detected and Quantified	29.0		11.8	59.8	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human	Detected and Quantified			6.9	13.4	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human	Detected and Quantified	7.8		3.8	25.1	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human	Detected and Quantified			8.1	18	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human	Detected and Quantified	8.5		4.9	17.1	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human	Detected and Quantified	12.772	10.179			Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	17.5		2.0	33.0	Adult (>18 years old)	Both	3-Hydroxyisobutyric aciduria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human	Detected and Quantified	225.0		60.0	390.0	Children (1-13 years old)	Both	3-Hydroxyisobutyric Aciduria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human	Detected and Quantified	13.39	6.588			Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	<95				Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human	Detected and Quantified	13.0		2.0	24.0	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	1.23	0.71			Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

Not Available

General References

Yoshida I, Sweetman L, Kulovich S, Nyhan WL, Robinson BH: Effect of lipoic acid in a patient with defective activity of pyruvate dehydrogenase, 2-oxoglutarate dehydrogenase, and branched-chain keto acid dehydrogenase. Pediatr Res. 1990 Jan;27(1):75-9. doi: 10.1203/00006450-199001000-00020. [PubMed:2104971 ]
Liebich HM, Dotzauer A, Tetschner B: Gas chromatographic determination of oxo- and hydroxycarboxylic acids in serum and urine of diabetic and normal subjects. J Chromatogr. 1989 May 12;468:157-65. doi: 10.1016/s0021-9673(00)96313-1. [PubMed:2732286 ]
Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. doi: 10.1016/s0009-8981(99)00210-7. [PubMed:10686279 ]
Chitayat D, Meagher-Villemure K, Mamer OA, O'Gorman A, Hoar DI, Silver K, Scriver CR: Brain dysgenesis and congenital intracerebral calcification associated with 3-hydroxyisobutyric aciduria. J Pediatr. 1992 Jul;121(1):86-9. doi: 10.1016/s0022-3476(05)82549-1. [PubMed:1625099 ]
Landaas S: Accumulation of 3-hydroxyisobutyric acid, 2-methyl-3-hydroxybutyric acid and 3-hydroxyisovaleric acid in ketoacidosis. Clin Chim Acta. 1975 Oct 15;64(2):143-54. doi: 10.1016/0009-8981(75)90196-5. [PubMed:126826 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Viegas CM, da Costa Ferreira G, Schuck PF, Tonin AM, Zanatta A, de Souza Wyse AT, Dutra-Filho CS, Wannmacher CM, Wajner M: Evidence that 3-hydroxyisobutyric acid inhibits key enzymes of energy metabolism in cerebral cortex of young rats. Int J Dev Neurosci. 2008 May-Jun;26(3-4):293-9. doi: 10.1016/j.ijdevneu.2008.01.007. Epub 2008 Feb 7. [PubMed:18329219 ]
Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for (S)-3-Hydroxyisobutyric acid (MMDBc0057091)

MOL for #<Metabolite:0x00007f121c47ae20>

3D MOL for #<Metabolite:0x00007f121c47ae20>

3D SDF for #<Metabolite:0x00007f121c47ae20>

3D-SDF for #<Metabolite:0x00007f121c47ae20>

PDB for #<Metabolite:0x00007f121c47ae20>

3D PDB for #<Metabolite:0x00007f121c47ae20>

SMILES for #<Metabolite:0x00007f121c47ae20>

INCHI for #<Metabolite:0x00007f121c47ae20>

Structure for #<Metabolite:0x00007f121c47ae20>

3D Structure for #<Metabolite:0x00007f121c47ae20>