ANGELICIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H6O3
Molecular Weight	186.1635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1OC2=C(C=CC3=C2C=CO3)C=C1

InChI

InChIKey=XDROKJSWHURZGO-UHFFFAOYSA-N

InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H

HIDE SMILES / InChI

Molecular Formula	C11H6O3
Molecular Weight	186.1635
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/3473010 | https://www.ncbi.nlm.nih.gov/pubmed/561302 | https://www.ncbi.nlm.nih.gov/pubmed/19684342 | https://www.ncbi.nlm.nih.gov/pubmed/27748898 | https://www.ncbi.nlm.nih.gov/pubmed/25352883 | https://www.ncbi.nlm.nih.gov/pubmed/24803987 | https://www.ncbi.nlm.nih.gov/pubmed/11169165

Angelicin (isopsoralen), is a furocoumarin, occuring in a number of plants belonging to the Umbelliferae family. It acts as a photosensitizer by forming DNA monoadducts. Angelicin is able to inhibit monoamine oxidase (MAO) activities in rat brain mitochondria. Angelicin exerts antineoplastic and antidiabetic properties in animal models.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/399905 \| https://www.ncbi.nlm.nih.gov/pubmed/6445206 \| https://www.ncbi.nlm.nih.gov/pubmed/561302 \| https://www.ncbi.nlm.nih.gov/pubmed/19684342	Binding Agent 1076
Monoamine oxidase A 52 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11169165	Inhibitor 8504	9.0 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11169165	Inhibitor 8504	12.8 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27748898 https://www.ncbi.nlm.nih.gov/pubmed/25352883	Primary	Preclinical	Unknown Approved Use Unknown
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27581277	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24803987	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Brd4 is essential for IL-1β-induced inflammation in human airway epithelial cells.	2014	24759736
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.	2013-05-02	23501157
Furocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice.	2012-02-25	22173200
Naturally occurring food toxins.	2010-09	22069686
Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage.	2010-07-01	20627596
A pterocarpan from the seeds of Bituminaria morisiana.	2010-07	20238177
Two new coumarins from the chloroform extract of Angelica urumiensis from Iran.	2010-04	20410639
Anti-influenza drug discovery: structure-activity relationship and mechanistic insight into novel angelicin derivatives.	2010-02-25	20092255
Pharmacokinetics, tissue distribution and excretion of coumarin components from Psoralea corylifolia L. in rats.	2010-02	20195822
Phytoestrogens from Psoralea corylifolia reveal estrogen receptor-subtype selectivity.	2010-02	19577453
Psoralea corylifolia Linn.-"Kushtanashini".	2010-01	22228944
Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry.	2010	20212330
Repair of laser-localized DNA interstrand cross-links in G1 phase mammalian cells.	2009-10-09	19684342
Simultaneous quantification of psoralen and isopsoralen in rat plasma by ultra-performance liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study after oral administration of Haigou Pill.	2009-10-01	19671498
Increase in gamma-globin mRNA content in human erythroid cells treated with angelicin analogs.	2009-10	19777196
Simultaneous determination of psoralen and isopsoralen in plasma and Chinese medicine Xian Ling Gu Bao capsule by using HPLC-DAD coupled with alternating trilinear decomposition algorithm.	2009-09-21	19720187
Simultaneous determination of seven components in Qibaomeiran pill by HPLC-DAD.	2009-09	19772753
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.	2009-09	19725558
Anti-collagenase, anti-elastase and anti-oxidant activities of extracts from 21 plants.	2009-08-04	19653897
Differentiation and apoptosis in UVA-irradiated cells treated with furocoumarin derivatives.	2009-08	19723073
Fetal Hemoglobin Inducers from the Natural World: A Novel Approach for Identification of Drugs for the Treatment of {beta}-Thalassemia and Sickle-Cell Anemia.	2009-06	18955291
The human oxidative DNA glycosylase NEIL1 excises psoralen-induced interstrand DNA cross-links in a three-stranded DNA structure.	2009-05-01	19258314
Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues.	2009-03-15	19230658
Isolation and functional characterization of CYP71AJ4 encoding for the first P450 monooxygenase of angular furanocoumarin biosynthesis.	2009-02-20	19098286
[Studies on chemical constituents from roots of Polygonum amplexicaule].	2009-01	19385182
Fetal globin induction in beta-thalassemia.	2009	20001626
Thiopyrano[2,3-e]indol-2-ones: angelicin heteroanalogues with potent photoantiproliferative activity.	2008-11-15	18951030
Comparison of the global genomic and transcription-coupled repair rates of different lesions in human cells.	2008-11-13	18998417
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008-10-15	18692084
Phytophotodermatitis in Rijeka region, Croatia.	2008-10	19138025
3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links.	2008-08-02	18571479
Furocoumarins photolysis products induce differentiation of human erythroid cells.	2008-07-24	18485726
An HPLC method for determination of oridonin in rabbits using isopsoralen as an internal standard and its application to pharmacokinetic studies for oridonin-loaded nanoparticles.	2008-06-15	18514594
Montelukast inhibits tumour necrosis factor-alpha-mediated interleukin-8 expression through inhibition of nuclear factor-kappaB p65-associated histone acetyltransferase activity.	2008-05	18325031
Real-time fluorescence-based detection of furanocoumarin photoadducts of DNA.	2008-04-11	18401857
Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544.	2008-02-15	18048073
Pharmacological targeting of NF-kappaB potentiates the effect of the topoisomerase inhibitor CPT-11 on colon cancer cells.	2008-01-29	18182997
Helicoverpa zea CYP6B8 and CYP321A1: different molecular solutions to the problem of metabolizing plant toxins and insecticides.	2007-12	18065401
Separation and determination of psoralen and isopsoralen by microemulsion electrokinetic chromatography.	2007-10	17582232
Fluorescent DNA probes: study of mechanisms of changes in spectral properties and features of practical application.	2007-08	17922647
[Study on micro-wave processed of Psoralea corylifolia with uniform and regression analysis].	2007-06	17802878
High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma.	2007-05-09	17344014
Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.	2007-04	17536725
Psoralen and isopsoralen, two coumarins of Psoraleae Fructus, can alleviate scopolamine-induced amnesia in rats.	2007-03	17318785
Induction of apoptosis in Jurkat cells by photoexcited psoralen derivatives: Implication of mitochondrial dysfunctions and caspases activation.	2007-03	17084583
Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis.	2007-01-05	17068340
A deficit of detoxification enzymes: pesticide sensitivity and environmental response in the honeybee.	2006-10	17069637
Dynamic regulation of Drosophila nuclear receptor activity in vivo.	2006-09	16914501
gamma-H2AX formation in response to interstrand crosslinks requires XPF in human cells.	2006-06-10	16678501
[Studies on chemical constituents in rhizome of Elaeagnus bockii I].	2006-06	17048645

Patents

Sample Use Guides

In Vivo Use Guide

The purpose of this study was to determine the protective effects of angelicin on allergic asthma induced by ovalbumin (OVA) in mice. Mice were sensitized to OVA (on days 0 and 14) and challenged with OVA three times (on days 21 to 23). Angelicin (2.5, 5, 10 mg/kg) was given intraperitoneally 1 h before OVA treatment after the initial OVA sensitization.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Angelicin increased cellular cytotoxicity against human SH-SY5Y neuroblastoma cells in a dose- and time-dependent manner with IC(50) of 49.56 μM at 48 h of incubation.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:43 GMT 2025`
Record UNII	CZZ080D7BD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPSORALEN

Preferred Name

English

ANGELICIN

Common Name

English

2H-FURO(2,3-H)-1-BENZOPYRAN-2-ONE

Systematic Name

English

ISOPSORALEN [HSDB]

Common Name

English

NSC-404563

Code

English

Code System Code Type Description

PUBCHEM

10658