Page last updated: 2024-11-13

(E)-5-hydroxy-6-(3-methylbut-2-enyl)-2-(pent-1-enyl)benzofuran-4-carbaldehyde

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

You've described a molecule with a rather complex structure, (E)-5-hydroxy-6-(3-methylbut-2-enyl)-2-(pent-1-enyl)benzofuran-4-carbaldehyde. While it's not a well-known compound with widespread research interest, its structure suggests it could be related to natural products or have potential applications in organic chemistry. Here's a breakdown of its characteristics and why it might be interesting for research:

**Structure:**

* **Benzofuran:** The core structure is benzofuran, a heterocyclic aromatic compound with a fused benzene and furan ring system. This is a common motif in natural products.
* **Substituents:** The molecule is decorated with various substituents:
* **Hydroxy group (OH):** This group often confers biological activity, potential for hydrogen bonding, or reactivity.
* **3-methylbut-2-enyl:** This side chain contains a double bond and a branched alkyl group.
* **Pent-1-enyl:** Another side chain with a double bond and a linear alkyl group.
* **Carbaldehyde (CHO):** This group is an aldehyde, often reactive and potentially useful in chemical synthesis.

**Potential Research Interest:**

* **Natural Product Analogue:** The structure suggests it could be a synthetic analog of a naturally occurring molecule. Many benzofurans are found in plants and have diverse biological activities. Studying this compound could provide insights into natural product synthesis and the relationship between structure and activity.
* **Organic Synthesis:** The molecule presents a challenge for synthetic chemists. The combination of multiple functional groups and stereochemistry (the E designation) makes it a potential target for developing novel synthetic methods.
* **Pharmacological Activity:** Although the specific activity is unknown, the presence of the hydroxy group, the double bonds, and the benzofuran ring system could suggest potential biological activities. Research could explore its effects on various biological systems.
* **Materials Science:** The compound's structure could lead to interesting properties in materials science. For instance, the presence of the aromatic ring system and double bonds could influence its optical or electronic properties.

**Importance for Research:**

The importance of this compound depends on its specific properties and the research goals. If it is a synthetic analog of a known natural product, its research importance would stem from understanding its activity compared to the natural source. If it's a novel compound, research would focus on exploring its unique properties and potential applications.

To truly understand its importance, we'd need more information about the specific research context, such as:

* **Where was it found or synthesized?**
* **What are the research goals?**
* **What are its biological, chemical, or physical properties?**

Without this context, it's difficult to determine its significance beyond its interesting structure and potential for research.

Cross-References

ID SourceID
PubMed CID44559107
CHEMBL ID462797
CHEBI ID68192
CHEBI ID68701

Synonyms (10)

Synonym
CHEMBL462797
chebi:68192 ,
2-(2',3-epoxy-(1->3')-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde
CHEBI:68701
5-hydroxy-6-(3-methylbut-2-en-1-yl)-2-[(1e)-pent-1-en-1-yl]-1-benzofuran-4-carbaldehyde
NCGC00386105-01
ncgc00386105-01_c19h22o3_5-hydroxy-6-(3-methyl-2-buten-1-yl)-2-[(1e)-1-penten-1-yl]-1-benzofuran-4-carbaldehyde
916602-30-7
DTXSID101130564
5-hydroxy-6-(3-methyl-2-buten-1-yl)-2-(1e)-1-penten-1-yl-4-benzofurancarboxaldehyde

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
Chaetomium metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Chaetomium.
Aspergillus metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
[role 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]

Drug Classes (3)

ClassDescription
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
aldehydeA compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1085767Antifungal activity against Pichia kudriavzevii ATCC 6258 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610906Binding affinity at human CB2 receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085764Antileishmanial activity against promastigote form of Leishmania donovani after 48 hr by alamar blue assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085761Cytotoxicity against Chlorocebus aethiops (African green monkey) Vero cells after 48 hr by neutral red assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085776Antibacterial activity against Staphylococcus aureus ATCC 292132012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085762Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hr by plasmodial LDH assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610903Binding affinity at human kappa opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085775Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 335912012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085773Antibacterial activity against Pseudomonas aeruginosa ATCC 278532012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085770Antifungal activity against Aspergillus fumigatus ATCC 2043052012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610905Binding affinity at human CB1 receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID610904Binding affinity at human mu opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085772Antibacterial activity against Mycobacterium intracellulare ATCC 230682012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085763Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 after 72 hr by plasmodial LDH assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID379514Antioxidant activity assessed as DPPH free radical scavenging activity2006Journal of natural products, Nov, Volume: 69, Issue:11
Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata.
AID1085777Antifungal activity against Cryptococcus neoformans ATCC 901132012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085771Antifungal activity against Candida albicans ATCC 900282012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085779Antifungal activity against Candida glabrata ATCC 900302012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610902Binding affinity at human delta opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085774Antibacterial activity against Escherichia coli ATCC 352182012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.26

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.26 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]