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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:33 UTC
Update Date2021-09-14 15:45:47 UTC
HMDB IDHMDB0032064
Secondary Accession Numbers
  • HMDB32064
Metabolite Identification
Common Name(S)-3-Butyl-1(3H)-isobenzofuranone
Description(S)-3-Butyl-1(3H)-isobenzofuranone, also known as N-butylphthalide or L-NBP CPD, belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone (S)-3-Butyl-1(3H)-isobenzofuranone is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Butyl-1(3H)-isobenzofuranone is a celery and herbal tasting compound. Outside of the human body, (S)-3-Butyl-1(3H)-isobenzofuranone is found, on average, in the highest concentration within wild celeries and lovages (S)-3-Butyl-1(3H)-isobenzofuranone has also been detected, but not quantified in, several different foods, such as celeriacs, celery stalks, dills, and parsley. This could make (S)-3-butyl-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods.
Structure
Data?1563862213
Synonyms
ValueSource
N-ButylphthalideHMDB
ColforsinHMDB
ForskolinHMDB
3-N-ButylphthalideHMDB
L-NBP CPDHMDB
(S)-(-)-3-ButylphthalideHMDB
Chemical FormulaC12H14O2
Average Molecular Weight190.2384
Monoisotopic Molecular Weight190.099379692
IUPAC Name3-butyl-1,3-dihydro-2-benzofuran-1-one
Traditional Namebutylphthalide
CAS Registry Number3413-15-8
SMILES
CCCCC1OC(=O)C2=C1C=CC=C2
InChI Identifier
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3
InChI KeyHJXMNVQARNZTEE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentBenzofuranones
Alternative Parents
Substituents
  • Isobenzofuranone
  • Phthalide
  • Benzofuranone
  • Isocoumaran
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP3ALOGPS
logP3.36ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.78 m³·mol⁻¹ChemAxon
Polarizability21.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-a60db6c280b6eaa60eb12017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9700000000-a60db6c280b6eaa60eb12021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-d904c229292bb1e0158f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5900000000-eaf37a164a20b7e346332016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9100000000-91e07caebaab8b4c09f12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2146ee7ffa48beef55f92016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0900000000-51103c4450b69b0a893b2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f97-3900000000-0a47a98e87c08ae044bb2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f778b0a41733b7c667b12021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-87c178dc0d4e990c1b992021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-5900000000-a54a8ddd5cde35355e322021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12749
Phenol Explorer Compound IDNot Available
FooDB IDFDB011862
KNApSAcK IDNot Available
Chemspider ID55293
KEGG Compound IDC17854
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61361
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .