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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 of BERGAPTEN

SMILES

COC1=C2C=CC(=O)OC2=CC3=C1C=CO3

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Geralen

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
[Heracl'eum mantegazzi'anum: photosensitization].
2001 Jan 18
Furanocoumarins in celery and parsnips: method and multiyear Canadian survey.
2001 Jul-Aug
Effects of silperisone on the excitation process in Ranvier nodes.
2001 Jun
Anaphylaxis to 5-methoxypsoralen during photochemotherapy.
2001 Nov
Indolopyridoquinazoline alkaloid from Leptothyrsa sprucei.
2001 Oct
Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice.
2001 Sep
Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds.
2001 Sep-Dec
Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri.
2002 Apr
Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips.
2002 Apr 24
Constituents of the fruits and leaves of Euodia daniellii.
2002 Dec
Simple and rapid determination of psoralens in topic solutions using liquid chromatography.
2002 Jan 1
Zabon phytophotodermatitis: first case reports due to Citrus maxima.
2002 May
Oral administration of 5-methoxypsoralen affects the distribution and metabolism of 2-aminofluorene in Sprague-Dawley rats.
2002 May-Jun
Constituents of Peucedanum zenkeri seeds and their antimicrobial effects.
2003 Aug
Markovian chemicals "in silico" design (MARCH-INSIDE), a promising approach for computer-aided molecular design I: discovery of anticancer compounds.
2003 Dec
Skin permeation of 5-methoxypsoralen from topical dosage forms.
2003 Feb
Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography.
2003 Jul 4
Antibacterial coumarins from Angelica gigas roots.
2003 Jun
Reproductive toxicity of the psoralens.
2003 May-Jun
Coumarins from Cnidium monnieri (L.) and their proliferation stimulating activity on osteoblast-like UMR106 cells.
2004 Aug
Inhibition of DNA polymerization and antifungal specificity of furanocoumarins present in traditional medicines.
2004 Jun
Phytotoxins from the leaves of Ruta graveolens.
2004 Jun 2
A method for fast determination of psoralens in oral solutions of phytomedicines using liquid chromatography.
2004 Oct 29
Citrus aurantium, an ingredient of dietary supplements marketed for weight loss: current status of clinical and basic research.
2004 Sep
Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams.
2005 Aug
Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents.
2005 Jul
Internet-based search of randomised trials relevant to mental health originating in the Arab world.
2005 Jul 26
Post-stress metabolism involves umbelliferone production in anthocyanin-producing and nonproducing cells of Glehnia littoralis suspension cultures.
2005 Jun
5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity.
2005 Mar
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 Nov-Dec
[Studies on chemical constituents from roots of Peucedanum praeruptorum II].
2006 Aug
Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen.
2006 Aug
Parsnip webworms and host plants at home and abroad: trophic complexity in a geographic mosaic.
2006 Dec
Efficacy of 8-methoxypsoralen vs. 5-methoxypsoralen plus ultraviolet A therapy in patients with mycosis fungoides.
2006 Mar
Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity.
2006 Sep
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007 Feb 26
Coumarins from Cnidium monnieri and their antiosteoporotic activity.
2007 Jan
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version).
2007 Jun
Burns caused by accidental overdose of photochemotherapy (PUVA).
2007 May
Herbal medicine today: clinical and research issues.
2007 Sep
[Simultaneous determination of 8-methoxypsoralen and 5-methoxypsoralen in cosmetics using LC-MS/MS].
2007 Sep
In vivo methods for the assessment of topical drug bioavailability.
2008 Jan
In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon.
2008 May
Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue).
2008 Oct
Patents

Patents

JP2003500094A
9
JP2012500628A
4

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 Fri Dec 15 15:54:01 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:01 GMT 2023
Record UNII
4FVK84C92X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BERGAPTEN
MI  
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
5-METHOXYPSORALEN
MART.   WHO-DD  
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
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
WHO-VATC QD05BA03
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL24171
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
HSDB
3466
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
FDA UNII
4FVK84C92X
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
DRUG BANK
DB12216
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
CHEBI
18293
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-604-5
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
CAS
484-20-8
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
PUBCHEM
2355
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
NSC
95437
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
RXCUI
15842
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY RxNorm
MESH
C022909
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1065345
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
SMS_ID
100000078282
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
DRUG CENTRAL
3021
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID1025560
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
EVMPD
SUB12695MIG
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
MERCK INDEX
m2430
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
BERGAPTEN
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
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PARENT -> CONSTITUENT ALWAYS PRESENT
ANGELICA ARCHANGELICA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
ANISE
PARENT -> CONSTITUENT ALWAYS PRESENT
PARSLEY
PARENT -> CONSTITUENT ALWAYS PRESENT
ANGELICA KEISKEI TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
CYTOCHROME P450 2A13
METABOLIC ENZYME -> SUBSTRATE
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Structure of 5,6-DIHYDRO-4-METHOXY-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE
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Structure of 6-HYDROXY-4-METHOXY-5-BENZOFURANPROPANOIC ACID
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Structure of 2,3-DIHYDRO-2,3-DIHYDROXY-4-METHOXY-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE
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Structure of 2H-1-BENZOPYRAN-2-ONE, 6-(1,2-DIHYDROXYETHYL)-7-HYDROXY-5-METHOXY-
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Structure of 7-HYDROXY-5-METHOXY-2-OXO-2H-1-BENZOPYRAN-6-ACETIC ACID
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Structure of METHOXSALEN
PARENT -> IMPURITY
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Related Record Type Details
Structure of BERGAPTEN
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