Page last updated: 2024-12-11

n(3)-(4-methoxyfumaroyl)-2,3-diaminopropionic acid

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

Description

N(3)-(4-methoxyfumaroyl)-2,3-diaminopropionic acid: inhibits glucosamine synthetase in E coli; structure given in first source; RN given refers to (S-(E)-isomer) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N(3)-(4-methoxyfumaroyl)-2,3-diaminopropionic acid : A monocarboxylic acid amide obtained by the formal condensation of the terminal amino group of 3-amino-L-alanine with the carboxy group of (2E)-4-methoxy-4-oxobut-2-enoic acid. [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]

Cross-References

ID SourceID
PubMed CID6438678
CHEMBL ID1911373
CHEBI ID74407
MeSH IDM0157894

Synonyms (16)

Synonym
fmdp
(2s)-2-amino-3-[[(e)-4-methoxy-4-oxobut-2-enoyl]amino]propanoic acid
(2s)-2-amino-3-{[(2e)-4-methoxy-4-oxobut-2-enoyl]amino}propanoic acid
3-{[(2e)-4-methoxy-4-oxobut-2-enoyl]amino}-l-alanine
2-butenoic acid, 4-((2-amino-2-carboxyethyl)amino)-4-oxo-, 1-methyl ester, (s-(e))-
n(3)-(4-methoxyfumaroyl)-l-2,3-diaminopropionic acid
96920-07-9
n(3)-(4-methoxyfumaroyl)-2,3-diaminopropionic acid
chebi:74407 ,
bdbm50356011
CHEMBL1911373 ,
Q27144653
2-butenoic acid, 4-[[(2s)-2-amino-2-carboxyethyl]amino]-4-oxo-, 1-methyl ester, (2e)-
1-methyl (2e)-4-[[(2s)-2-amino-2-carboxyethyl]amino]-4-oxo-2-butenoate
DTXSID601153658
AKOS040748370
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)IC50 (µMol)0.40000.40000.40000.4000AID625555
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
UDP-N-acetylglucosamine biosynthetic processGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
energy reserve metabolic processGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
glutamine metabolic processGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
circadian regulation of gene expressionGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
UDP-N-acetylglucosamine metabolic processGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
fructose 6-phosphate metabolic processGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
protein N-linked glycosylationGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
glutamine-fructose-6-phosphate transaminase (isomerizing) activityGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
carbohydrate derivative bindingGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
extracellular exosomeGlutamine--fructose-6-phosphate aminotransferase [isomerizing] 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1191330Antimicrobial activity against Pseudomonas aeruginosa ATCC 2756 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1191324Antimicrobial activity against Candida glabrata DSM 11226 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1191323Antimicrobial activity against Candida albicans ATCC 10231 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1717679Inhibition of Candida albicans AMB-25 glucosamine-6-phosphate synthase using glutamine as substrate incubated for 30 mins2020Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21
Recent Progress in the Discovery of Antifungal Agents Targeting the Cell Wall.
AID1191329Antimicrobial activity against Bacillus subtilis ATCC 9372 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1191325Antimicrobial activity against Candida parapsilosis DSM 5784 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1717678Antifungal activity against Candida albicans AMB-25 incubated for 48 hrs by serial two-fold dilution method2020Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21
Recent Progress in the Discovery of Antifungal Agents Targeting the Cell Wall.
AID1313290Antimicrobial activity against Candida glabrata DSM 11226 after 48 hrs by serial two fold dilution method2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Synthesis and biological activity of novel ester derivatives of N(3)-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase.
AID1313292Antimicrobial activity against Escherichia coli PCM 2560 after 24 hrs by serial two fold dilution method2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Synthesis and biological activity of novel ester derivatives of N(3)-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase.
AID1313289Antimicrobial activity against Candida albicans ATCC 10231 after 48 hrs by serial two fold dilution method2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Synthesis and biological activity of novel ester derivatives of N(3)-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase.
AID1191331Inhibition of Candida albicans glucosamine-6-phosphate synthase assessed as glucosamine-6-phosphate by Elson-Morgan method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1717677Competitive inhibition of Candida albicans AMB-25 glucosamine synthetase using glutamine as substrate incubated for 30 mins by Lineweaver-Burk plot based Dixon plot analysis2020Journal of medicinal chemistry, 11-12, Volume: 63, Issue:21
Recent Progress in the Discovery of Antifungal Agents Targeting the Cell Wall.
AID1191327Antimicrobial activity against Staphylococcus epidermidis PCM 2118 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1191332Binding affinity to immobilized artificial membrane PC DD2 (unknown origin) by UV/Vis detector model2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1313293Inhibition of Candida albicans glucosamine-6-phosphate synthase expressed in Escherichia coli using D-fructose-6-phosphate as substrate after 30 mins2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Synthesis and biological activity of novel ester derivatives of N(3)-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase.
AID1191328Antimicrobial activity against Escherichia coli PCM 2560 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID1313291Antimicrobial activity against Staphylococcus aureus ATCC 29213 after 24 hrs by serial two fold dilution method2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Synthesis and biological activity of novel ester derivatives of N(3)-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase.
AID1191326Antimicrobial activity against Staphylococcus aureus ATCC 29213 assessed as growth inhibition serial 2-fold dilution microtitre plate method2015European journal of medicinal chemistry, Jan-27, Volume: 90Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.
AID625555Irreversible inhibition of GFAT2011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (8.70)18.7374
1990's9 (39.13)18.2507
2000's5 (21.74)29.6817
2010's6 (26.09)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.76

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 Index11.76 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (8.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]