BERGAPTEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H8O4
Molecular Weight	216.1895
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C=COC2=CC3=C1C=CC(=O)O3

InChI

InChIKey=BGEBZHIAGXMEMV-UHFFFAOYSA-N

InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

HIDE SMILES / InChI

Molecular Formula	C12H8O4
Molecular Weight	216.1895
Charge	0
Count

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

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00533195 | doi:10.1186/s12943-015-0403-4 retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498523 |

Bergapten, known as 5-methoxypsoralen, a cumarine-derivate compound, presents in many fruits and vegetables. It has shown antitumor effects in a variety of cell types. The key target of bergapten action in breast cancer cells was identified the oncosuppressor gene PTEN (phosphatase tensin homolog deleted from chromosome 10); bergapten by inducing PTEN expression, produces autophagy in breast cancer cells. Besides, bergapten is under investigation in clinical trial phase III for patients with severe generalized atopic dermatitis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphatase tensin homologue deleted from chromosome 10 1 Target ID: Phosphatase tensin homologue deleted from chromosome 10 Sources: doi:10.1186/s12943-015-0403-4 retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498523/	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 64 Sources: https://clinicaltrials.gov/ct2/show/NCT00533195	Primary		Phase III 665	Geralen Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26148846	Primary		Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
175 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
108 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
322 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
1754 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1757 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3282 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
276 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
942 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
1.2 mg/kg 1 times / day multiple, oral Studied dose Dose: 1.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 1.2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	Other AEs: Vomiting... Other AEs: Vomiting (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/

AEs

AE	Significance	Dose	Population
Vomiting	4%	1.2 mg/kg 1 times / day multiple, oral Studied dose Dose: 1.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 1.2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/

PubMed

Title	Date	PubMed
Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue).	2008-10	18211259
In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon.	2008-05	18337075
Effective biotic elicitation of Ruta graveolens L. shoot cultures by lysates from Pectobacterium atrosepticum and Bacillus sp.	2008-03	17968510
Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544.	2008-02-15	18048073
Induction of gamma-globin mRNA, erythroid differentiation and apoptosis in UVA-irradiated human erythroid cells in the presence of furocumarin derivatives.	2008-02-15	18022602
Enhancement of bone morphogenetic protein-2 expression and bone formation by coumarin derivatives via p38 and ERK-dependent pathway in osteoblasts.	2008-01-28	17980360
In vivo methods for the assessment of topical drug bioavailability.	2008-01	17985216
Inhibition on human liver cytochrome P450 3A4 by constituents of fennel (Foeniculum vulgare): identification and characterization of a mechanism-based inactivator.	2007-12-12	17988092
Irritant and cytotoxic coumarins from Angelica glauca Edgew roots.	2007-12-07	18058380
Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors.	2007-12-07	18052337
Herbal medicine today: clinical and research issues.	2007-09	18227931
[Simultaneous determination of 8-methoxypsoralen and 5-methoxypsoralen in cosmetics using LC-MS/MS].	2007-09	18161337
[Simultaneous determination of 5 active components in Fructus Cnidii by HPLC].	2007-09	18051896
Coumarins from Peucedanum luxurians.	2007-09	17582700
Quality assessment of Rhizoma et Radix Notopterygii by HPTLC and HPLC fingerprinting and HPLC quantitative analysis.	2007-07-27	17512692
Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae).	2007-07-25	17532157
Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.	2007-07	17452418
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version).	2007-06	17497162
Burns caused by accidental overdose of photochemotherapy (PUVA).	2007-05	17218059
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007-02-26	17324258
Coumarins from Cnidium monnieri and their antiosteoporotic activity.	2007-01	17315308
[Studies on chemical constituents from fruits of Paliurus ramosissimus].	2006-12	17357553
Parsnip webworms and host plants at home and abroad: trophic complexity in a geographic mosaic.	2006-12	17249232
Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1.	2006-09	16762476
Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity.	2006-09	16497474
[Studies on chemical constituents from roots of Peucedanum praeruptorum II].	2006-08	17061553
Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen.	2006-08	16972199
Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar.	2006-04	16640727
A method for quantitative determination of furanocoumarins in capsules and tablets of phytochemical preparations.	2006-04	16595942
Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus.	2006-03	16572296
Efficacy of 8-methoxypsoralen vs. 5-methoxypsoralen plus ultraviolet A therapy in patients with mycosis fungoides.	2006-03	16445785
[Studies on chemical constituents in roots of Heracleum rapula].	2006-02	16706022
Variations in content of active ingredients causing drug interactions in grapefruit juice products sold in California.	2006	16841515
Effects of 5-methoxypsoralen (5-MOP) on arylamine N-acetyltransferase activity in the stomach and colon of rats and human stomach and colon tumor cell lines.	2005-11-10	16277023
Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides.	2005-11-01	16140017
Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams.	2005-08	16124408
Internet-based search of randomised trials relevant to mental health originating in the Arab world.	2005-07-26	16045805
Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents.	2005-07	15997104
Post-stress metabolism involves umbelliferone production in anthocyanin-producing and nonproducing cells of Glehnia littoralis suspension cultures.	2005-06	16008093
Antioxidant activity of citrus limonoids, flavonoids, and coumarins.	2005-03-23	15769128
5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity.	2005-03	15801679
Secondary metabolites of Peucedanum tauricum fruits.	2005-03	15771895
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.	2005-01	15702516
Phototoxicity of protoporphyrin IX, diarginine diprotoporphyrinate and N,N-diphenylalanyl protoporphyrin toward human fibroblasts and keratinocytes in vitro: effect of 5-methoxypsoralen.	2004-12-30	15623335
Preparative isolation and purification of bergapten and imperatorin from the medicinal plant Cnidium monnieri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.	2004-12-17	15633744
2D NMR spectroscopic analyses of archangelicin from the seeds of Angelica archangelica.	2004-12	15634612
A method for fast determination of psoralens in oral solutions of phytomedicines using liquid chromatography.	2004-10-29	15496338
Genetic variation in primary metabolites of Pastinaca sativa; can herbivores act as selective agents?	2004-10	15609832
[Study on coumarin compounds from Exocarpium Citri Grandis].	2004-08	15658818
Coumarins from Cnidium monnieri (L.) and their proliferation stimulating activity on osteoblast-like UMR106 cells.	2004-08	15378857

Patents

Sample Use Guides

In Vivo Use Guide

1,2 mg/kg 2 hours before UVA irradiation p.o. 3 times weekly for 5 weeks

Route of Administration: Oral

In Vitro Use Guide

Bone marrow stromal cells (BMSCs) were cultured in osteogenic induction medium with the addition of bergapten for 2 weeks. The concentrations of bergapten used were 0.1, 1, and 10 μmol/L in vitro. Bergapten promotes the expression of alkaline phosphatase (ALP) by BMSCs in vitro in a dose-dependent manner, as revealed by ALP staining.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:32 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:32 GMT 2025`
Record UNII	4FVK84C92X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-METHOXYPSORALEN

Preferred Name

English

BERGAPTEN

Common Name

English

5-METHOXYPSORALEN [IARC]

Common Name

English

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

Systematic Name

English

BERGAPTEN [MI]

Common Name

English

METHOXSALEN RELATED COMPOUND A [USP-RS]

Common Name

English

GERALEN

Common Name

English

METHOXSALEN RELATED COMPOUND A [USP IMPURITY]

Common Name

English

5-METHOXYPSORALEN [MART.]

Common Name

English

BERGAPTENE

Common Name

English

MAJUDIN

Common Name

English

NSC-95437

Code

English

BERGAPTAN

Common Name

English

HERACLIN

Common Name

English

5-methoxypsoralen [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D05BA03