Compounds > Isobergapten
Page last updated: 2024-11-06

Isobergapten

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Isobergapten is a linear furanocoumarin naturally occurring in plants such as Umbelliferae, Rutaceae, and Moraceae. It exhibits phototoxic and cytotoxic properties, and research has focused on its potential applications in medicine and agriculture. Isobergapten is known to be a potent inhibitor of DNA synthesis and has shown promising activity against various cancer cell lines. It also exhibits antimicrobial and antiviral properties. The synthesis of isobergapten typically involves the reaction of umbelliferone with isoprene in the presence of a Lewis acid catalyst. Due to its phototoxic nature, isobergapten has been investigated for its potential use as a photochemotherapeutic agent for skin cancers. Additionally, its antimicrobial properties make it a subject of study for its potential application in agriculture as a biopesticide. Research on isobergapten continues to explore its various biological activities and potential therapeutic applications.'

Cross-References

ID SourceID
PubMed CID68082
CHEMBL ID141690
CHEBI ID81487
SCHEMBL ID2253427

Synonyms (62)

Synonym
BRD-K31678817-001-02-0
KBIO1_001192
DIVK1C_006248
SDCCGMLS-0066519.P001
SPECTRUM_000630
SPECTRUM5_000029
BSPBIO_002672
MEGXP0_000707
NCGC00178537-01
isobergapten
smr000156214
MLS000574855
NCGC00095572-01
482-48-4
KBIO2_003678
KBIOGR_001929
KBIO2_001110
KBIO2_006246
KBIO3_002172
KBIOSS_001110
SPECTRUM4_001445
SPECTRUM2_000313
SPECPLUS_000152
SPECTRUM3_001226
SPBIO_000306 ,
SPECTRUM300032
NCGC00095572-02
CHEMBL141690
chebi:81487 ,
isobergaptene
AKOS000277832
5-methoxyfuro[2,3-h]chromen-2-one
C18082
NCGC00095572-03
5-methoxy-2h-furo(2,3-h)-1-benzopyran-2-one
2h-furo(2,3-h)-1-benzopyran-2-one, 5-methoxy-
27x3v737wh ,
unii-27x3v737wh
HMS2201F13
S9557
CCG-38589
FT-0603415
2h-furo[2,3-h]-1-benzopyran-2-one, 5-methoxy-
HMS3330D17
5-methoxy-2h-furo[2,3-h]chromen-2-one
iso-bergapten
5-methoxyangelicin
5-benzofuranacrylic acid, 4-hydroxy-6-methoxy-, .delta.-lactone
mfcd00016756
5-methoxy-angelicin
SCHEMBL2253427
AJSPSRWWZBBIOR-UHFFFAOYSA-N
5-methoxy-2h-furo[2,3-h]chromen-2-one #
AC-34979
DTXSID8075415
SR-01000721827-2
sr-01000721827
Q27155416
HY-N0764
BRD-K31678817-001-06-1
CS-0009791
MS-23185
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
furanocoumarinAny furochromene that consists of a furan ring fused with a coumarin. The fusion may occur in different ways in give several isomers.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (24)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
Microtubule-associated protein tauHomo sapiens (human)Potency0.12590.180013.557439.8107AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency12.96760.011212.4002100.0000AID1030
isocitrate dehydrogenase 1, partialHomo sapiens (human)Potency50.11876.309627.099079.4328AID602179
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency100.00000.035520.977089.1251AID504332
gemininHomo sapiens (human)Potency2.05960.004611.374133.4983AID624297
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID7887Compound was evaluated for cell growth inhibition against A 431 cell line by irradiation in the presence of examined compound1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
4'-Methyl derivatives of 5-MOP and 5-MOA: synthesis, photoreactivity, and photobiological activity.
AID76049Compound was tested for skin photosensitizing potency in guinea pig, after exposure to 50 microg cm e-2,and 20 kJ m e-2 of UVA; Absent1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
4'-Methyl derivatives of 5-MOP and 5-MOA: synthesis, photoreactivity, and photobiological activity.
AID88514Compound was evaluated for cell growth inhibition against HeLa cell line by irradiation in the presence of examined compound1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
4'-Methyl derivatives of 5-MOP and 5-MOA: synthesis, photoreactivity, and photobiological activity.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID82835Compound was evaluated for cell growth inhibition against HL 60 cell line by irradiation in the presence of examined compound1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
4'-Methyl derivatives of 5-MOP and 5-MOA: synthesis, photoreactivity, and photobiological activity.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (10.00)18.2507
2000's1 (10.00)29.6817
2010's6 (60.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.74 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methoxsalen
Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.		1.9910aromatic ether;
psoralens		antineoplastic agent;
cross-linking reagent;
dermatologic drug;
photosensitizing agent;
plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Palmoplantaris Pustulosis
[description not available]		01.9910
Psoriasis
A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.		01.9910
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Benign Neoplasms
[description not available]		03.0310
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0310
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310