Hmdb loader
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
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:33 UTC
Update Date2021-10-13 06:21:04 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 3-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 a celery and herbal tasting compound (S)-3-Butyl-1(3H)-isobenzofuranone is found, on average, in the highest concentration within wild celeries (Apium graveolens) and lovages (Levisticum officinale) (S)-3-Butyl-1(3H)-isobenzofuranone has also been detected, but not quantified in, several different foods, such as celeriacs (Apium graveolens var. rapaceum), celery stalks (Apium graveolens var. dulce), dills (Anethum graveolens), and parsleys (Petroselinum crispum). This could make (S)-3-butyl-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-3-Butyl-1(3H)-isobenzofuranone.
Structure
Data?1563862213
Synonyms
ValueSource
(S)-(-)-3-ButylphthalideMeSH
3-N-ButylphthalideMeSH
N-ButylphthalideMeSH
L-NBP CPDMeSH
ColforsinHMDB
ForskolinHMDB
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

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point177.00 to 178.00 °C. @ 15.00 mm HgThe Good Scents Company Information System
Water Solubility199.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.800The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP10(3) g/LALOGPS
logP10(3.36) g/LChemAxon
logS10(-3.5) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.01631661259
DarkChem[M-H]-140.26331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-3-Butyl-1(3H)-isobenzofuranoneCCCCC1OC(=O)C2=C1C=CC=C22596.9Standard polar33892256
(S)-3-Butyl-1(3H)-isobenzofuranoneCCCCC1OC(=O)C2=C1C=CC=C21592.5Standard non polar33892256
(S)-3-Butyl-1(3H)-isobenzofuranoneCCCCC1OC(=O)C2=C1C=CC=C21661.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-a60db6c280b6eaa60eb12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 10V, Positive-QTOFsplash10-0006-1900000000-d904c229292bb1e0158f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 20V, Positive-QTOFsplash10-0006-5900000000-eaf37a164a20b7e346332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 40V, Positive-QTOFsplash10-0k96-9100000000-91e07caebaab8b4c09f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 10V, Negative-QTOFsplash10-000i-0900000000-2146ee7ffa48beef55f92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 20V, Negative-QTOFsplash10-000b-0900000000-51103c4450b69b0a893b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 40V, Negative-QTOFsplash10-0f97-3900000000-0a47a98e87c08ae044bb2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 10V, Negative-QTOFsplash10-000i-0900000000-f778b0a41733b7c667b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 20V, Negative-QTOFsplash10-000i-0900000000-87c178dc0d4e990c1b992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 40V, Negative-QTOFsplash10-0059-5900000000-a54a8ddd5cde35355e322021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 10V, Positive-QTOFsplash10-0006-0900000000-00db18150d760fe6b5762021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 20V, Positive-QTOFsplash10-00kf-5900000000-8734ee9e85c67c76ae912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Butyl-1(3H)-isobenzofuranone 40V, Positive-QTOFsplash10-0690-9200000000-20cd801d5d09a00b292e2021-09-25Wishart LabView 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
Good Scents IDrw1013781
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.. .