Compounds > syringolin a
Page last updated: 2024-11-13

syringolin a

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

Description

syringolin A: a cyclic dipeptide composed of the two non-proteinogenic amino acids [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

syringolin A : A syrbactin that has a (3E,9E)-2,7-dioxo-1,6-diazacyclododeca-3,9-diene skeleton that is substituted by an isopropyl group at position 5 and by a [(2S)-2-({[(1S)-1-carboxy-2-methylpropyl]carbamoyl}amino)-3-methylbutanoyl]nitrilo group at the 8-pro-S position. It is produced by the pathogenic bacterium Pseudomonas syringae pv. syringae. [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 CID23724545
CHEBI ID181397
MeSH IDM0361645

Synonyms (6)

Synonym
2-[[1-[[(3e,9e)-2,7-dioxo-5-propan-2-yl-1,6-diazacyclododeca-3,9-dien-8-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoylamino]-3-methylbutanoic acid
CHEBI:181397
2-(3-(1-(((4e,10e)-2,9-dioxo-12-isopropyl-1,8-diazacyclododecane-4,10-diene-3-yl)carbamoyl)-2-methylpropyl)ureido)-3-methylbutyric acid
syringolin a
212115-96-3
AKOS040735349

Research Excerpts

Overview

Syringolin A (SylA) is a nonribosomal cyclic peptide. It is produced by the bacterial pathogen Pseudomonas syringae pv syringAE that can inhibit the eukaryotic proteasome. Syringsolin A was shown to be a virulence factor for P.syringae.

ExcerptReferenceRelevance
"Isosyringolin A, which is an isomer of the proteasome-inhibiting natural product syringolin A, was designed and synthesized to develop analogues that are step economical and synthetically accessible in a practical manner. "( Design, Synthesis, and Biological Activity of Isosyringolin A.
Chiba, T; Ichikawa, S; Iida, S; Kitahata, S; Matsuda, A; Ri, M; Yoshida, T, 2016)		1.31
"Syringolin A was shown to be a virulence factor for P."( Pseudomonas syringae virulence factor syringolin A counteracts stomatal immunity by proteasome inhibition.
Dudler, R; Ramel, C; Schellenberg, B, 2010)		1.35
"Syringolin A (SylA) is a nonribosomal cyclic peptide produced by the bacterial pathogen Pseudomonas syringae pv syringae that can inhibit the eukaryotic proteasome. "( Proteasome activity imaging and profiling characterizes bacterial effector syringolin A.
Clerc, J; Gu, C; Kaiser, M; Kaschani, F; Kolodziejek, I; Krahn, D; Misas-Villamil, JC; Niessen, S; Overkleeft, HS; van der Hoorn, RA; Verdoes, M; Willems, LI, 2011)		2.04
"Syringolin A is an unusual derivative of a tripeptide that contains a 12-membered ring consisting of the amino acids 5-methyl-4-amino-2-hexenoic acid and 3,4-dehydrolysine, two nonproteinogenic amino acids."( Functional analysis of genes involved in the synthesis of syringolin A by Pseudomonas syringae pv. syringae B301 D-R.
Amrein, H; Dudler, R; Granado, J; Makart, S; Schneider-Pokorny, J; Shakya, R, 2004)		1.29
"Syringolin A is a new plant elicitor produced by the plant pathogen Pseudomonas syringae pv. "( Syringolin A, a new plant elicitor from the phytopathogenic bacterium Pseudomonas syringae pv. syringae, inhibits the proliferation of neuroblastoma and ovarian cancer cells and induces apoptosis.
Bachmann, AS; Coleman, CS; Dudler, R; Michel, K; Park, DJ; Rocetes, JP; Wallick, CJ; Warn-Cramer, BJ, 2006)		3.22
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[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]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's9 (23.08)29.6817
2010's28 (71.79)24.3611
2020's2 (5.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.04

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 Index11.04 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydrogen carbonate
Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.		2.0510carbon oxoanioncofactor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		4.6680isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.0810amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.0510L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		2.4620diazine;
pyrazines		Daphnia magna metabolite
bortezomib
[no description available]		7.7830amino acid amide;
L-phenylalanine derivative;
pyrazines		antineoplastic agent;
antiprotozoal drug;
protease inhibitor;
proteasome inhibitor
glidobactin a
glidobactin A: structure given in first source; isolated from polyangium brachysporum & Pseudomonas		9.4160
epoxomicin
[no description available]		3.5820morpholines;
tripeptide		proteasome inhibitor
syringomycin
syringomycin: from Pseudomonas syringae; phytotoxin; small peptide containing molecule. syringomycin : A class of cyclodepsipeptides which are secreted by the plant pathogen Pseudomonas syringae. Composed from nine nonribosomally synthesised amino acids bonded to a fatty acid hydrocarbon tail.		2.0210
syringolin b
syringolin B: a proteasome inhibitor isolated from Pseudomonas syringae; structure in first source		4.5570
ConditionIndicatedRelationship StrengthStudiesTrials
Kahler Disease
[description not available]		03.0240
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		03.0240
B16 Melanoma
[description not available]		02.1710
Infection, Wound
[description not available]		02.0810
Degenerative Diseases, Central Nervous System
[description not available]		0310
Neurodegenerative Diseases
Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.		0310
Experimental Leukemia
[description not available]		02.0510
Cancer of Ovary
[description not available]		02.4420
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		07.7430
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.4420
Hematologic Malignancies
[description not available]		02.0610
Hematologic Neoplasms
Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.		02.0610
Benign Neoplasms
[description not available]		02.0710
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.		02.0710
Neoplasms, Nervous System
[description not available]		02.0310