Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:59:07 UTC
Update Date2022-09-22 18:34:54 UTC
HMDB IDHMDB0341406
Secondary Accession NumbersNone
Metabolite Identification
Common Nametriacetate lactone
Descriptiontriacetate lactone belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. triacetate lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Triacetic acid lactone (TAL; 4-hydroxy-6-methyl-2-pyrone) is an organic compound derived enzymatically from glucose. This enzyme catalyzes the synthesis of triacetic acid lactone from acetyl-CoA via two subsequent condensations with malonyl-CoA. The tautomer on the left, featuring a 4-hydroxy group, the C4 carbon, is dominant. It is also a precursor to sorbic acid, dienoic acid, and hexenoic acid. The microbial synthesis of triacetic acid lactone requires the enzyme 2-pyrone synthase (2-PS).
Structure
Thumb
Synonyms
ValueSource
4-Hydroxy-6-methyl-2-pyroneChEBI
Triacetic acid lactoneGenerator
Chemical FormulaC6H6O3
Average Molecular Weight126.111
Monoisotopic Molecular Weight126.031694053
IUPAC Name4-hydroxy-6-methyl-2H-pyran-2-one
Traditional Nametriacetic acid lactone
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=CC(=O)O1
InChI Identifier
InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3
InChI KeyNSYSSMYQPLSPOD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.03ALOGPS
logP0.55ChemAxon
logS-0.22ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.81 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00037933
Chemspider IDNot Available
KEGG Compound IDC02752
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriacetic acid lactone
METLIN IDNot Available
PubChem Compound54675757
PDB IDNot Available
ChEBI ID16458
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]