Page last updated: 2024-12-11

(2R,4R)-4-(1-acetyl-3-indolyl)-2-[[4-(hydroxymethyl)phenyl]methoxy]-N-(phenylmethyl)-3,4-dihydro-2H-pyran-6-carboxamide

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

The compound you described, (2R,4R)-4-(1-acetyl-3-indolyl)-2-[[4-(hydroxymethyl)phenyl]methoxy]-N-(phenylmethyl)-3,4-dihydro-2H-pyran-6-carboxamide, is a synthetic molecule with a complex structure. It's important to understand that this is not a naturally occurring compound but rather a molecule created in a lab for specific research purposes.

Here's a breakdown of its structure and potential significance in research:

**Structure:**

* **Core:** The molecule is built around a 3,4-dihydro-2H-pyran ring system.
* **Substituents:**
* A 1-acetyl-3-indolyl group is attached at the 4th position of the pyran ring. Indoles are aromatic heterocycles often found in biologically active compounds.
* A 4-(hydroxymethyl)phenyl group is attached at the 2nd position via an ether linkage. This benzyl alcohol derivative could potentially contribute to the molecule's ability to interact with biological systems.
* A phenylmethyl (benzyl) group is attached to the nitrogen atom of a carboxamide group at the 6th position. This makes the molecule an amide.
* **Stereochemistry:** The molecule is chiral, with specific stereochemistry defined as (2R,4R). This means the substituents at positions 2 and 4 are arranged in a specific configuration. This is crucial in drug development as different enantiomers can have drastically different biological effects.

**Potential Importance in Research:**

The complex structure and presence of various functional groups suggest that this compound might exhibit interesting biological properties. Here's why it could be important in research:

* **Potential Drug Candidate:** The combination of functional groups and the chiral nature suggests it might interact with specific biological targets. Researchers might be investigating this compound as a potential drug candidate for various diseases.
* **Biological Activity Studies:** Researchers could be exploring its effects on cells, tissues, or organisms. This could include studying its pharmacological properties, potential toxicity, or interactions with specific receptors.
* **Structure-Activity Relationship (SAR) Studies:** The compound could be part of a series of related molecules with varying structures. This is crucial for understanding how changes in chemical structure affect biological activity.
* **Synthetic Chemistry Development:** The synthesis of this complex molecule could itself be an interesting research area, contributing to the development of new synthetic methods or strategies.

**To understand the exact research focus and significance of this specific compound, you would need to consult the original research publications or papers where it is described.**

Remember, the importance of a compound is often specific to a particular research project or field of study.

Cross-References

ID SourceID
PubMed CID6668464
CHEMBL ID1560289
CHEBI ID121959

Synonyms (12)

Synonym
smr000442048
MLS000834643
DHPC1.1_000003
DHPC1_000730 ,
DHPC1.1_000065
DHPC1.1_000007
CHEBI:121959
(2r,4r)-4-(1-acetylindol-3-yl)-n-benzyl-2-[[4-(hydroxymethyl)phenyl]methoxy]-3,4-dihydro-2h-pyran-6-carboxamide
HMS2226J19
CHEMBL1560289
(2r,4r)-4-(1-acetyl-3-indolyl)-2-[[4-(hydroxymethyl)phenyl]methoxy]-n-(phenylmethyl)-3,4-dihydro-2h-pyran-6-carboxamide
Q27210581
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indolesAny compound containing an indole skeleton.
[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 (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency3.54810.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency17.74070.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency17.78280.177814.390939.8107AID2147
glp-1 receptor, partialHomo sapiens (human)Potency11.22020.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency8.19610.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency4.53460.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency25.11890.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency44.66840.100022.9075100.0000AID485364
Smad3Homo sapiens (human)Potency22.38720.00527.809829.0929AID588855
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency15.84890.011212.4002100.0000AID1030
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency10.00000.28189.721235.4813AID2326
67.9K proteinVaccinia virusPotency11.29470.00018.4406100.0000AID720579; AID720580
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency0.70790.707936.904389.1251AID504333
importin subunit beta-1 isoform 1Homo sapiens (human)Potency63.09575.804836.130665.1308AID540263
snurportin-1Homo sapiens (human)Potency63.09575.804836.130665.1308AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency56.23410.425612.059128.1838AID504891
gemininHomo sapiens (human)Potency18.35640.004611.374133.4983AID624296
Rap guanine nucleotide exchange factor 3Homo sapiens (human)Potency100.00006.309660.2008112.2020AID720709
Guanine nucleotide-binding protein GHomo sapiens (human)Potency6.30961.995325.532750.1187AID624288
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
alternatively spliced Trp4Mus musculus (house mouse)EC50 (µMol)8.41330.00033.337010.5907AID434937
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
adaptive immune responseRap guanine nucleotide exchange factor 3Homo sapiens (human)
signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 3Homo sapiens (human)
associative learningRap guanine nucleotide exchange factor 3Homo sapiens (human)
Rap protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of actin cytoskeleton organizationRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
intracellular signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of GTPase activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of protein export from nucleusRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of stress fiber assemblyRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
establishment of endothelial barrierRap guanine nucleotide exchange factor 3Homo sapiens (human)
cellular response to cAMPRap guanine nucleotide exchange factor 3Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein domain specific bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
cortical actin cytoskeletonRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
microvillusRap guanine nucleotide exchange factor 3Homo sapiens (human)
endomembrane systemRap guanine nucleotide exchange factor 3Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
lamellipodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
filopodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
extracellular exosomeRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (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: 12.56

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 Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]