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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:07:23 UTC
Update Date2022-03-07 02:54:03 UTC
HMDB IDHMDB0034312
Secondary Accession Numbers
  • HMDB34312
Metabolite Identification
Common NameIsopimpinellin
DescriptionIsopimpinellin belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. Isopimpinellin is found, on average, in the highest concentration within a few different foods, such as parsleys (Petroselinum crispum), celery stalks (Apium graveolens var. dulce), and fennels (Foeniculum vulgare). Isopimpinellin has also been detected, but not quantified in, several different foods, such as parsnips (Pastinaca sativa), limes (Citrus aurantiifolia), wild carrots (Daucus carota), anises (Pimpinella anisum), and lemons (Citrus limon). This could make isopimpinellin a potential biomarker for the consumption of these foods. Isopimpinellin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Isopimpinellin.
Structure
Data?1563862544
Synonyms
ValueSource
5,8-DimethoxypsoralenChEBI
5,8-DimethoxypsoraleneChEBI
4,9-Dimethoxy-7-oxofuro[3,2-g]chromeneHMDB
4,9-Dimethoxy-7H-furo(3,2-g) (1)benzopyran-7-oneHMDB
4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-oneHMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-oneHMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
4,9-Dimethoxy-furo[3,2-g]chromen-7-oneHMDB
4,9-DimethoxypsoralenHMDB
5, 8-DimethoxypsoraleneHMDB
5,8-Dimethoxy-6,7-furanocoumarinHMDB
7H-furo(3,2-g)(1)Benzopyran-7-one, 4,9-dimethoxy- (8ci)HMDB
DimethylpsoralenHMDB
Isopimpinellin (4,9-dimethoxypsoralen)HMDB
Chemical FormulaC13H10O5
Average Molecular Weight246.218
Monoisotopic Molecular Weight246.052823422
IUPAC Name4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one
Traditional Nameisopimpinellin
CAS Registry Number482-27-9
SMILES
COC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2
InChI Identifier
InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
InChI KeyDFMAXQKDIGCMTL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 5-methoxypsoralen
  • 8-methoxypsoralen
  • 1-benzopyran
  • Benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point151 °CNot Available
Boiling Point448.00 to 449.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility315.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.407 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available146.461http://allccs.zhulab.cn/database/detail?ID=AllCCS00001428
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.01ALOGPS
logP1.63ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.32 m³·mol⁻¹ChemAxon
Polarizability23.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.48731661259
DarkChem[M-H]-156.13531661259
DeepCCS[M+H]+152.90530932474
DeepCCS[M-H]-150.54730932474
DeepCCS[M-2H]-183.43730932474
DeepCCS[M+Na]+158.99930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsopimpinellinCOC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C23200.6Standard polar33892256
IsopimpinellinCOC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C22107.0Standard non polar33892256
IsopimpinellinCOC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C22228.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isopimpinellin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1190000000-275fee6a0dc6bf75820a2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopimpinellin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopimpinellin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000t-7690000000-e6fa32711c30bc1868162014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-001i-0090000000-a0c532fce25db07d90ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-001i-0090000000-54e2a9d485cc8bdceb6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-001i-0090000000-1032f4d166b576b7ff202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-001i-0090000000-9c87bfda7e5ffe9c5af42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-0udi-0190000000-ea38f4e14acc089f6b512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin Linear Ion Trap , positive-QTOFsplash10-0udi-0190000000-a3f55b3b5507de3ae9992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin , positive-QTOFsplash10-014i-0970000000-1e191da648efe9b73b122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin , positive-QTOFsplash10-014i-0290000000-bdc222e3350bd6ef64862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin , positive-QTOFsplash10-014j-0190000000-908c9053908baf8cf9542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOFsplash10-07vr-0920000000-5af7d91dde7af1b895472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOFsplash10-014i-0190000000-dfa5b17d7b2df4661d052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOFsplash10-0002-0090000000-278fc8d7828591790af92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOFsplash10-0002-0090000000-49418fa141b50d6f7f712016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOFsplash10-0002-0090000000-730804c160e7a2b01bf92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOFsplash10-014i-0390000000-ee25336a941ea1bf779b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 10V, Negative-QTOFsplash10-0002-0090000000-bbb8af93a94542f5b6532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 20V, Negative-QTOFsplash10-0002-0090000000-cef1eff8d1ded6b77f3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 40V, Negative-QTOFsplash10-0fki-0960000000-d96e6099792968341c942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 10V, Negative-QTOFsplash10-0002-0090000000-f541a876b9ec3249e2092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 20V, Negative-QTOFsplash10-0002-0090000000-05d9c28202aea63dacbe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 40V, Negative-QTOFsplash10-000i-0920000000-1148e3f152ca14bca10d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 10V, Positive-QTOFsplash10-0002-0090000000-14343c13950e873267f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 20V, Positive-QTOFsplash10-0002-0090000000-14343c13950e873267f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopimpinellin 40V, Positive-QTOFsplash10-0002-0090000000-aa4ade1addb5f0cbc93a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
Phenol Explorer Compound ID720
FooDB IDFDB012661
KNApSAcK IDC00000583
Chemspider ID61391
KEGG Compound IDC02162
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsopimpinellin
METLIN IDNot Available
PubChem Compound68079
PDB IDNot Available
ChEBI ID28853
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1102171
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.. .