ContaminantDB: Isopimpinellin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-08 21:38:42 UTC

Update Date

2026-04-06 02:12:56 UTC

Accession Number

CHEM000737

Identification

Common Name

Isopimpinellin

Class

Small 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
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,8-Dimethoxypsoralen	ChEBI
5,8-Dimethoxypsoralene	ChEBI
4,9-Dimethoxy-7-oxofuro[3,2-g]chromene	HMDB
4,9-Dimethoxy-7H-furo(3,2-g) (1)benzopyran-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one	HMDB
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9ci	HMDB
4,9-Dimethoxy-furo[3,2-g]chromen-7-one	HMDB
4,9-Dimethoxypsoralen	HMDB
5, 8-Dimethoxypsoralene	HMDB
5,8-Dimethoxy-6,7-furanocoumarin	HMDB
7H-furo(3,2-g)(1)Benzopyran-7-one, 4,9-dimethoxy- (8ci)	HMDB
Dimethylpsoralen	HMDB
Isopimpinellin (4,9-dimethoxypsoralen)	HMDB

Chemical Formula

C₁₃H₁₀O₅

Average Molecular Mass

246.218 g/mol

Monoisotopic Mass

246.053 g/mol

CAS Registry Number

482-27-9

IUPAC Name

4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

isopimpinellin

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 Key

DFMAXQKDIGCMTL-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:28853 )
Furanocoumarins (C02162 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	151°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.32 m³·mol⁻¹	ChemAxon
Polarizability	23.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1190000000-275fee6a0dc6bf75820a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-a0c532fce25db07d90ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-54e2a9d485cc8bdceb6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-1032f4d166b576b7ff20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-9c87bfda7e5ffe9c5af4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-ea38f4e14acc089f6b51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-a3f55b3b5507de3ae999	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0970000000-1e191da648efe9b73b12	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0290000000-bdc222e3350bd6ef6486	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014j-0190000000-908c9053908baf8cf954	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-07vr-0920000000-5af7d91dde7af1b89547	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0190000000-dfa5b17d7b2df4661d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-278fc8d7828591790af9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-49418fa141b50d6f7f71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-730804c160e7a2b01bf9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0390000000-ee25336a941ea1bf779b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-bbb8af93a94542f5b653	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-cef1eff8d1ded6b77f3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fki-0960000000-d96e6099792968341c94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-f541a876b9ec3249e209	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-05d9c28202aea63dacbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0920000000-1148e3f152ca14bca10d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-14343c13950e873267f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-14343c13950e873267f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0090000000-aa4ade1addb5f0cbc93a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000t-7690000000-e6fa32711c30bc186816	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Isopimpinelin 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not 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/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

The 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.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034312

FooDB ID