Page last updated: 2024-12-10

(2S)-2-(3-oxo-1H-isoindol-2-yl)-3-phenylpropanoic acid

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

**(2S)-2-(3-oxo-1H-isoindol-2-yl)-3-phenylpropanoic acid** is a chemical compound, also known as **(S)-Phthaloyl-D-phenylalanine**, a derivative of the amino acid phenylalanine.

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

**Structure:**

* **(2S)-2-:** Indicates the stereochemistry at the second carbon atom. S stands for Sinister and indicates a specific arrangement of substituents around the chiral center.
* **(3-oxo-1H-isoindol-2-yl):** This part refers to a phthalimide group, which is a cyclic imide derived from phthalic acid. It's attached to the second carbon atom.
* **3-phenylpropanoic acid:** This is the core structure of the molecule, a phenyl ring attached to a propanoic acid chain.

**Importance in Research:**

(2S)-2-(3-oxo-1H-isoindol-2-yl)-3-phenylpropanoic acid has potential applications in various research fields:

* **Drug Discovery:** The phthalimide group, along with the chiral center, makes this compound a versatile starting point for synthesizing novel pharmaceuticals. Phthalimides are known for their diverse pharmacological activities, including anti-inflammatory, analgesic, and antimicrobial properties.
* **Materials Science:** This compound might be useful for developing new polymers or other materials. The phthalimide group can be used to introduce specific functional groups or create cross-linking points in polymers.
* **Biochemistry:** The compound's relationship to phenylalanine makes it relevant for studying protein synthesis and metabolism. It could be used as a probe to investigate the function of enzymes involved in phenylalanine metabolism.
* **Chemical Synthesis:** The presence of the phthalimide group offers possibilities for chemical modification and synthesis of other molecules. This makes the compound useful as a building block in organic chemistry.

**Specific Applications:**

* **Anti-cancer Research:** Some phthalimides have shown anti-cancer activity, and derivatives of this compound might be explored for their potential in treating specific types of cancer.
* **Alzheimer's Disease Research:** The phthalimide group is being investigated for its potential role in inhibiting the aggregation of amyloid-beta peptides, which are linked to Alzheimer's disease.

**Important Note:**

While this compound holds promise for research, its exact properties and applications are still under investigation. Further research is required to fully understand its potential and develop specific applications in the aforementioned fields.

Cross-References

ID SourceID
PubMed CID5309580
CHEMBL ID42210
CHEBI ID115478
SCHEMBL ID4203635

Synonyms (31)

Synonym
MLS-0062459.0001
smr000097543
MLS000120700 ,
CHEBI:115478
CHEMBL42210
HMS1625C21
AKOS001502795
(2s)-2-(3-oxo-1h-isoindol-2-yl)-3-phenylpropanoic acid
STK921979
(2s)-2-(1-oxo-1,3-dihydro-2h-isoindol-2-yl)-3-phenylpropanoic acid
CCG-131342
HMS2243F14
BBL033508
SCHEMBL4203635
(2s)-2-(1-ketoisoindolin-2-yl)-3-phenyl-propionic acid
bdbm43779
(2s)-2-(3-oxidanylidene-1h-isoindol-2-yl)-3-phenyl-propanoic acid
cid_5309580
Q27197331
SR-01000127050-1
sr-01000127050
E72280
105776-76-9
VS-12112
mfcd11868494
(2s)-2-(1-oxo-2,3-dihydro-1h-isoindol-2-yl)-3-phenylpropanoic acid
(2r/2s)-2-(1-oxo-1,3-dihydro-2h-isoindol-2-yl)-3-phenylpropanoic acid
CS-0215836
EN300-302900
(2s)-2-(1-oxo-2,3-dihydro-1h-isoindol-2-yl)-3-phenylpropanoicacid
Z1824566412
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenylalanine derivativeAn amino acid derivative resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of phenylalanine by a heteroatom. The definition normally excludes peptides containing phenylalanine residues.
[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 (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency1.99530.044717.8581100.0000AID485294
15-lipoxygenase, partialHomo sapiens (human)Potency39.81070.012610.691788.5700AID887
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency89.12510.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency79.43280.035520.977089.1251AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mcl-1Homo sapiens (human)IC50 (µMol)22.29000.40007.134454.0000AID1418
X-linked inhibitor of apoptosisHomo sapiens (human)IC50 (µMol)154.06000.31300.31300.3130AID1449; AID1514
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)IC50 (µMol)22.29000.00052.773925.1700AID1418
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)IC50 (µMol)22.29000.00052.891925.1700AID1418
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)IC50 (µMol)22.29000.00052.747825.1700AID1418
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)IC50 (µMol)22.29000.00052.780225.1700AID1418
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)IC50 (µMol)22.29000.00053.314249.5000AID1418
Mu-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)200.00000.00010.887410.0000AID1514
M17 leucyl aminopeptidasePlasmodium falciparum 3D7IC50 (µMol)6.47001.000027.8360138.0800AID1619
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
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
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.
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.
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.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID40958Antimicrobial activity against aspergillus sp and Candida albicans; Inactive2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID70243Minimum inhibitory concentration against Escherichia coli.2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID1190386Inhibition of baker's yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranoside as substrate incubated with enzyme for 10 mins prior to substrate challenge for 15 mins by microplate reader analysis2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Erinacerins C-L, isoindolin-1-ones with α-glucosidase inhibitory activity from cultures of the medicinal mushroom Hericium erinaceus.
AID1190387Cytotoxicity against human A549 cells after 72 hrs by MTT assay2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Erinacerins C-L, isoindolin-1-ones with α-glucosidase inhibitory activity from cultures of the medicinal mushroom Hericium erinaceus.
AID164543Minimum inhibitory concentration against Pseudomonas aeruginosa2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID125768Minimum inhibitory concentration against Micrococcus roseus2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID206715Compound was evaluated for minimum inhibitory concentration against Staphylococcus aureus2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID40960Antimicrobial activity against gram positive and gram negative bacteria; Active2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID40764Minimum inhibitory concentration against Bacillus subtilis2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives.
AID1190388Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Erinacerins C-L, isoindolin-1-ones with α-glucosidase inhibitory activity from cultures of the medicinal mushroom Hericium erinaceus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's6 (66.67)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.63

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 Index12.63 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]