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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:07:23 UTC
Update Date2019-07-23 06:15:44 UTC
HMDB IDHMDB0034312
Secondary Accession Numbers
  • HMDB34312
Metabolite Identification
Common NameIsopimpinellin
DescriptionIsopimpinellin, also known as dimethylpsoralen, 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. Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Isopimpinellin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isopimpinellin is found, on average, in the highest concentration within a few different foods, such as parsley, celery stalks, and fennels. Isopimpinellin has also been detected, but not quantified in, several different foods, such as carrots, parsnips, anises, limes, and wild celeries. This could make isopimpinellin a potential biomarker for the consumption of these foods. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). Isopimpinellin is a potentially toxic compound. Isopimpinelin strongly inhibits insulin-stimulated lipogenesis. All photobiological effects of furocoumarins result from their photochemical reactions. There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). It induces hepatic GSTs and is potent inhibitor of cytochrome P450 1A1/1B1.
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1190000000-275fee6a0dc6bf75820aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-a0c532fce25db07d90efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-54e2a9d485cc8bdceb6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-1032f4d166b576b7ff20Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-9c87bfda7e5ffe9c5af4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-ea38f4e14acc089f6b51Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-a3f55b3b5507de3ae999Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0970000000-1e191da648efe9b73b12Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0290000000-bdc222e3350bd6ef6486Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014j-0190000000-908c9053908baf8cf954Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-49418fa141b50d6f7f71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-730804c160e7a2b01bf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0390000000-ee25336a941ea1bf779bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-bbb8af93a94542f5b653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-cef1eff8d1ded6b77f3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fki-0960000000-d96e6099792968341c94Spectrum
MSMass Spectrum (Electron Ionization)splash10-000t-7690000000-e6fa32711c30bc186816Spectrum
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 ID
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.. .