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Showing Compound Isopimpinellin (FDB012661)

Record Information
Version1.0
Creation date2010-04-08 22:10:17 UTC
Update date2019-11-26 03:07:20 UTC
Primary IDFDB012661
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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), wild celeries (Apium graveolens), wild carrots (Daucus carota), limes (Citrus aurantiifolia), and anises (Pimpinella anisum). This could make isopimpinellin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isopimpinellin.
CAS Number482-27-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
4,9-dimethoxy-7H-furo(3,2-G) (1)benzopyran-7-onebiospider
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
7H-Furo(3,2-g)(1)benzopyran-7-one, 4,9-dimethoxy- (8CI)biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy-biospider
Isopimpinellin (4,9-Dimethoxypsoralen)biospider
Predicted 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
Chemical FormulaC13H10O5
IUPAC name4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2
Average Molecular Weight246.218
Monoisotopic Molecular Weight246.052823422
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.42%; H 4.09%; O 32.49%DFC
Melting PointMp 151°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data311 (e 13800) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000t-7690000000-e6fa32711c30bc1868162014-09-20View Spectrum
Predicted GC-MSIsopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1190000000-275fee6a0dc6bf75820aSpectrum
Predicted GC-MSIsopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsopimpinellin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-a0c532fce25db07d90ef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-54e2a9d485cc8bdceb6d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-1032f4d166b576b7ff202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-9c87bfda7e5ffe9c5af42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-ea38f4e14acc089f6b512017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-a3f55b3b5507de3ae9992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0970000000-1e191da648efe9b73b122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0290000000-bdc222e3350bd6ef64862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014j-0190000000-908c9053908baf8cf9542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-07vr-0920000000-5af7d91dde7af1b895472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-dfa5b17d7b2df4661d052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-278fc8d7828591790af92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-49418fa141b50d6f7f712016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-730804c160e7a2b01bf92016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0390000000-ee25336a941ea1bf779b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-bbb8af93a94542f5b6532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-cef1eff8d1ded6b77f3d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fki-0960000000-d96e6099792968341c942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-f541a876b9ec3249e2092021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-05d9c28202aea63dacbe2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0920000000-1148e3f152ca14bca10d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-14343c13950e873267f52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-14343c13950e873267f52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0090000000-aa4ade1addb5f0cbc93a2021-09-24View Spectrum
NMR
TypeDescriptionView
ChemSpider ID61391
ChEMBL IDCHEMBL140796
KEGG Compound IDC02162
Pubchem Compound ID68079
Pubchem Substance IDNot Available
ChEBI ID28853
Phenol-Explorer ID720
DrugBank IDNot Available
HMDB IDHMDB34312
CRC / DFC (Dictionary of Food Compounds) IDHJP62-Y:HJP62-Y
EAFUS IDNot Available
Dr. Duke IDISOPIMPINELLIN
BIGG IDNot Available
KNApSAcK IDC00000583
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti appetant50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lipogenicDUKE
anti mitoticDUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
mutagenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
piscicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.