PIMPINELLIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10O5
Molecular Weight	246.2155
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C2=C(OC(=O)C=C2)C3=C1OC=C3

InChI

InChIKey=BQPRWZCEKZLBHL-UHFFFAOYSA-N

InChI=1S/C13H10O5/c1-15-11-7-3-4-9(14)18-10(7)8-5-6-17-12(8)13(11)16-2/h3-6H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C13H10O5
Molecular Weight	246.2155
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6627920
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21214482 | https://www.ncbi.nlm.nih.gov/pubmed/10719903 | https://www.ncbi.nlm.nih.gov/pubmed/24257925 |

Pimpinellin is a furocoumarin and mevalonic acid derivative, that was isolated from Heracleum laciniatum and Toddalia asiatica. Pimpinellin, isopimpinellin and phellopterin are three major coumarins present in Toddalia asiatica extract which demonstrated activities like anticancer, vasodilative and antioxidant etc Pimpinellin is well known photoreactive compound and it is used in Brazil in some pharmaceutical and cosmetic products because of their UV-light absorbing properties

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21749864	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vitiligo 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10719903	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.	2013-05-02	23501157
Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry.	2010-02-15	20116347
Phytophotodermatitis in Rijeka region, Croatia.	2008-10	19138025
Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS.	2008-10	18705001
A pimpinellin monomer and dimer isolated from the roots of Esenbeckia grandiflora.	2004-12	15579978
Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica.	2004-06-19	15202601
The furanocoumarins in the roots of Heracleum sibiricum L.	2004-03-10	15005423

Patents

Sample Use Guides

In Vivo Use Guide

20 mkl of 0.25% absolute alcoholic solutions were applied to the back for 1 hour by the l inn chamber method

Route of Administration: Topical

In Vitro Use Guide

Pimpinellin isolated from the Traditional Chinese medicine was studied for their antitumor activity in vitro by determining the inhibitory percentage against growth of human epidermal carcinoma cell line A432 and human mammary cancer cell line BCAP, respectively. Pimpinellin inhibited growth of human epidermal carcinoma cell line A432 with IC50=73mkM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:51:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:51:54 GMT 2025`
Record UNII	D419UK1B4L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIMPINELLIN

Common Name

English

6,7-DIMETHOXYANGELICIN

Preferred Name

English

PIMPINELIN

Common Name

English

PIMPINELLINE

Common Name

English

PIMPINECILIN

Common Name

English

PIMPINELLIN [MI]

Common Name

English

2H-FURO(2,3-H)-1-BENZOPYRAN-2-ONE, 5,6-DIMETHOXY-

Systematic Name

English

5,6-DIMETHOXY-2H-FURO(2,3-H)-1-BENZOPYRAN-2-ONE

Systematic Name

English

Code System Code Type Description

CAS

131-12-4