Showing metabocard for Levulinic acid (BMDB0000720)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:28 UTC
Update Date2020-05-11 20:29:29 UTC
BMDB IDBMDB0000720
Secondary Accession Numbers
  • BMDB00720
Metabolite Identification
Common NameLevulinic acid
DescriptionLevulinic acid, also known as laevulinsaeure or levulate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Levulinic acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Levulinic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Acetylpropionic acidChEBI
3-Ketobutane-1-carboxylic acidChEBI
4-Ketovaleric acidChEBI
4-Oxovaleric acidChEBI
beta-Acetylpropionic acidChEBI
gamma-Ketovaleric acidChEBI
LAEVULINIC ACIDChEBI
LaevulinsaeureChEBI
LEVAChEBI
Levulic acidChEBI
LevulinsaeureChEBI
3-AcetylpropionateGenerator
3-Ketobutane-1-carboxylateGenerator
4-KetovalerateGenerator
4-OxovalerateGenerator
b-AcetylpropionateGenerator
b-Acetylpropionic acidGenerator
beta-AcetylpropionateGenerator
Β-acetylpropionateGenerator
Β-acetylpropionic acidGenerator
g-KetovalerateGenerator
g-Ketovaleric acidGenerator
gamma-KetovalerateGenerator
Γ-ketovalerateGenerator
Γ-ketovaleric acidGenerator
LAEVULINateGenerator
LevulateGenerator
LevulinateGenerator
4-OxopentanoateHMDB
4-Oxopentanoic acidHMDB
DiasporalHMDB
Levulinic acid, sodium saltHMDB
Magnesium diasporalHMDB
Calcium levulateHMDB
Magnesium levulinateHMDB
Calcium levulinateHMDB
Levulinic acid, ammonium saltHMDB
Levulinic acid, calcium saltHMDB
Magnesium laevulinateHMDB
Levulinic acidChEBI
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name4-oxopentanoic acid
Traditional Namelevulinic acid
CAS Registry Number123-76-2
SMILES
CC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyJOOXCMJARBKPKM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Short-chain keto acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 - 33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.49HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.14ALOGPS
logP-0.069ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.09 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000720
DrugBank IDDB02239
Phenol Explorer Compound IDNot Available
FooDB IDFDB003296
KNApSAcK IDC00051252
Chemspider ID11091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevulinic_acid
METLIN ID2195
PubChem Compound11579
PDB IDNot Available
ChEBI ID45630
References
Synthesis ReferenceCai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong. Review on preparation methods of levulinic acid, a new platform chemical. Xiandai Huagong (2003), 23(4), 14-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available