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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Methylbutyrolactone (HMDB02167)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:39 -0600
Update Date 2013-02-08 17:11:29 -0700
HMDB ID HMDB02167
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Methylbutyrolactone
Description 3-methylbutyrolactone is lactone of 4-hydroxyisovaleric acid and it has been found in the urine of patients with isovaleric acidemia, an autosomal recessive genetic disorder of the enzyme isovaleryl-CoA dehydrogenase (PMID 6452974 Link_out; PMID 6616835 Link_out). Isovaleric acidemia is closely related to the genetic metabolic disorder Maple syrup urine disease.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-(-)-3-Methyl-gamma-butyrolactone
  2. (S)-Dihydro-4-methylfuran-2(3H)-one
  3. 4-Methyldihydro-2(3H)-furanone
  4. Dihydro-4-methyl-2(3H)-Furanone
  5. S-beta-Methyl-gamma-butyrolactone
Chemical Formula C5H8O2
Average Molecular Weight 100.1158
Monoisotopic Molecular Weight 100.0524295
IUPAC Name 4-methyloxolan-2-one
Traditional IUPAC Name 4-methyloxolan-2-one
CAS Registry Number 1679-49-8
SMILES CC1COC(=O)C1
InChI Identifier InChI=1S/C5H8O2/c1-4-2-5(6)7-3-4/h4H,2-3H2,1H3
InChI Key ALZLTHLQMAFAPA-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Lactones
Sub Class N/A
Other Descriptors
  • Carboxylic Acid Esters
  • Oxolanes
Substituents
  • N/A
Direct Parent Lactones
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 0.41 ALOGPS
LogP 0.51 ChemAxon
LogS -0.04 ALOGPS
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 26.3 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 24.78 ChemAxon
Polarizability 10.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022879
KNApSAcK ID Not Available
Chemspider ID 88906 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02167 Link_out
Metagene Link HMDB02167 Link_out
METLIN ID 6521 Link_out
PubChem Compound 98451 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Beavers, William Anthony; Ignatchenko, Alexey Victorovitch. Process for preparing a- and b-methyl-g-butyrolactone and 3-methyltetrahydrofuran. Eur. Pat. Appl. (2004), 26 pp.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Divry P, Vianey-Liaud C, Cotte J: Routine gas chromatographic/mass spectrometric analysis of urinary organic acids. Results over a three-year period. Biomed Environ Mass Spectrom. 1987 Nov;14(11):663-8. Pubmed: 2962675 Link_out
  2. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. Pubmed: 6452974 Link_out
  3. Burke DG, Halpern B, Malegan D, McCairns E, Danks D, Schlesinger P, Wilken B: Profiles of urinary volatiles from metabolic disorders characterized by unusual odors. Clin Chem. 1983 Oct;29(10):1834-8. Pubmed: 6616835 Link_out