ISOPIMPINELLIN

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=C2OC=CC2=C(OC)C3=C1OC(=O)C=C3

InChI

InChIKey=DFMAXQKDIGCMTL-UHFFFAOYSA-N

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

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/8881335
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12376476 | https://www.ncbi.nlm.nih.gov/pubmed/28556437 | https://www.ncbi.nlm.nih.gov/pubmed/25240925

Isopimpinellin is a natural product synthesized by Umbelliferae (or Apiaceae), also known as the carrot or parsley family. It can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. There have been several studies looking into the effects of Isopimpinellin and other so-called naturally occurring coumarins (such as bergamottin and Imperatorin) as anticarcinogens.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22222157	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12376476	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Constituents of the fruits and leaves of Euodia daniellii.	2002 Dec	12510833
[Studies on the coumarins in the root of Zanthoxylum dimorphophyllum].	2003 Apr	15139146
[Quantification of isopimpinellin in root of Toddalia asiatica by HPLC].	2004 Aug	15506290
Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster.	2004 Jul 14	15237943
Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica.	2004 May-Jun	15202601
Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.	2005 Feb 15	15670584
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.	2005 Jan	15702516
Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants.	2005 Mar	15861043
In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon.	2008 May	18337075
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008 Oct 15	18692084
Botanical origin of Indian celery seed (fruit).	2009 Jul	19214654
Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats.	2009 Jul 29	19640308
Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells.	2010 Mar	19883747
Naturally occurring food toxins.	2010 Sep	22069686
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.	2013 May 2	23501157

Patents

Sample Use Guides

In Vivo Use Guide

35, 70 and 150 mg/kg

Route of Administration: Oral

In Vitro Use Guide

RAW264.7 cells were seeded in 96-well plates and maintained in DMEM supplemented with 5% FBS, 100 U/ml penicillin, and 100 mg/ml streptomycin. After incubation at 37 °C for 24 h, compounds were added into the media and incubated for 4 h. Then LPS (1 mg/ml) was added and co-incubated for another 24 h. After that, the supernatant of the media was mixed with an equal volume of Griess reagent. Nitrite production was determined by measuring the optical density at 540 nm.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:05:09 GMT 2023` Edited by `admin` on `Fri Dec 15 19:05:09 GMT 2023`
Record UNII	20GCF755G6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPIMPINELLIN

Common Name

English

5,8-DIMETHOXY-6,7-FURANOCOUMARIN

Common Name

English

METHOXSALEN RELATED COMPOUND B [USP IMPURITY]

Common Name

English

8-METHOXYBERGAPTEN

Common Name

English

NSC-401288

Code

English

ISO-PIMPINELLIN

Common Name

English

METHOXSALEN RELATED COMPOUND B [USP-RS]

Common Name

English

5,8-DIMETHOXYPSORALEN

Common Name

English

NSC-217988

Code

English

7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 4,9-DIMETHOXY-

Systematic Name

English

5-METHOXYXANTHOTOXIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45597