Isopimpinellin (CHEM000737)

Record Information
Version1.0
Creation Date2009-06-08 21:38:42 UTC
Update Date2026-08-18 22:31:50 UTC
Accession NumberCHEM000737
Identification
Common NameIsopimpinellin
ClassSmall Molecule
Description
Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Ester
  • Ether
  • Food Toxin
  • Furocoumarin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass246.218 g/mol
Monoisotopic Mass246.053 g/mol
CAS Registry Number482-27-9
IUPAC Name4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one
Traditional Nameisopimpinellin
SMILESCOC1=C2OC=CC2=C(OC)C2=C1OC(=O)C=C2
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
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point151°C
Boiling PointNot Available
SolubilityNot 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
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityIsopimpinelin strongly inhibits insulin-stimulated lipogenesis. It induces hepatic GSTs and is potent inhibitor of cytochrome P450 1A1/1B1. Oral administration of isopimpinellin, blocks DNA adducts formation and skin tumor initiation by 7,12-dimehylbenz[a]anthracene in SENCAR mice and in mouse mammary gland (5). 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. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (5)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. 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). (4)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsThe furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (4). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (1). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (6) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0034312
FooDB IDFDB012661
Phenol Explorer ID720
KNApSAcK IDC00000583
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsopimpinellin
Chemspider ID61391
ChEBI ID28853
PubChem Compound ID68079
Kegg Compound IDC02162
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.