Page last updated: 2024-11-05

acetosyringone

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

Description

Acetosyringone is a phenolic compound that occurs naturally in plants, particularly in wounded tissues and flowers. It acts as a signaling molecule, mediating interactions between plants and microbes. Acetosyringone is involved in the induction of virulence genes in Agrobacterium tumefaciens, a bacterium that causes crown gall disease in plants. The compound is also a potent elicitor of defense responses in plants, triggering the production of phytoalexins and other antimicrobial compounds. Acetosyringone is synthesized from the precursor ferulic acid through a series of enzymatic reactions. Its synthesis is regulated by various environmental factors, including wounding, pathogen attack, and the presence of specific microbes. The biological activity of acetosyringone is attributed to its ability to bind to specific receptors on the surface of microbial cells and plant cells. Acetosyringone is an important tool for researchers studying plant-microbe interactions, as it can be used to manipulate the expression of genes involved in pathogenicity and defense. It is also being investigated for its potential use in plant biotechnology, for example, in the development of disease-resistant crops and in the production of valuable plant compounds.'

acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. [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 CID17198
CHEMBL ID224146
CHEBI ID2404
SCHEMBL ID15511
MeSH IDM0146980

Synonyms (83)

Synonym
smr000112388
MLS002207209
brn 1966119
acetophenone, 3,5-dimethoxy-4-hydroxy-
acetosyringenin
ccris 7286
4-hydroksy-3',5'-dwumetoksyacetofenon [polish]
3,5-dimethoxy-4-hydroxyacetophenone
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
einecs 219-610-5
BRD-K66643401-001-02-4
4'-hydroxy-3',5'-dimethoxyacetophenone
1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one
4-hydroxy-3,5-dimethoxyacetophenone
CHEBI:2404 ,
acetophenone, 4'-hydroxy-3',5'-dimethoxy-
ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-
DIVK1C_007051
SDCCGMLS-0066948.P001
SPECTRUM4_001953
SPECTRUM_001915
SPECTRUM5_000695
BSPBIO_002850
2478-38-8
acetosyringone
inchi=1/c10h12o4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12h,1-3h
3',5'-dimethoxy-4'-hydroxyacetophenone, 97%
acetosyringon
NCGC00095819-01
KBIO1_001995
KBIO3_002070
KBIO2_005018
KBIOSS_002457
KBIO2_007586
KBIO2_002450
KBIOGR_002389
SPBIO_000418
SPECTRUM2_000429
SPECTRUM3_001115
SPECPLUS_000955
SPECTRUM300610
NCGC00095819-02
CHEMBL224146
3',5'-dimethoxy-4'-hydroxyacetophenone
BMSE000576
BMSE010032
D2666
A5075
1-(4-hydroxy-3,5-dimethoxy-phenyl)ethanone
AKOS005258861
unii-866p45y84s
866p45y84s ,
4-hydroksy-3',5'-dwumetoksyacetofenon
1-(3,5-dimethoxy-4-oxidanyl-phenyl)ethanone
A817490
CCG-39967
FT-0634308
S4955
4-acetyl-2,6-dimethoxyphenol
3', 5'-dimethoxy-4'-hydroxyacetophenone
SCHEMBL15511
DTXSID2062454
W-107282
A1-00327
4-acetylsyringol
phenol, 4-acetyl-2,6-dimethoxy
mfcd00008748
4'-hydroxy-3',5'-dimethoxyacetophenone, 97%
sr-05000002436
SR-05000002436-1
F20446
STL555160
HY-W009884
Q906309
CS-W010600
BRD-K66643401-001-04-0
BBL101364
4-hydroxy-3,5-dimethoxyacetophennone
MS-20205
EN300-112111
4 inverted exclamation mark -hydroxy-3 inverted exclamation mark ,5 inverted exclamation mark -dimethoxyacetophenone
SY049152
Z1255450019

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
anti-asthmatic drugA drug used to treat asthma.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
peripheral nervous system drugA drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
acetophenonesA class or aromatic ketone consisting of acetophenone, PhC(=O)CH3, and its substituted derivatives.
dimethoxybenzeneAny methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.
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]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency19.95260.35487.935539.8107AID624170
gemininHomo sapiens (human)Potency2.90930.004611.374133.4983AID624296
lamin isoform A-delta10Homo sapiens (human)Potency0.00710.891312.067628.1838AID1487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID399953Increase in genetic transformation in tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as callus formation at 100 uM after 4 weeks2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID282834Activity against caspase-mediated apoptosis in mouse L1210 cells2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study.
AID399957Toxicity in tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as detrimental genetic transformation at 500 uM after 4 weeks2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID399948Decrease in virH gene expression in Agrobacterium tumefaciens A348 overexpressing pSM219 virH::lacZ assessed as beta-galactosidase activity at >=250 uM after 18 hrs2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID399954Increase in genetic transformation in tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as buds formation at 100 uM after 4 weeks2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID399949Toxicity in Agrobacterium tumefaciens A348 overexpressing pSM219 virH::lacZ assessed as null effect at 5 mM after 18 hrs2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID282835Cytotoxicity against mouse L1210 cells2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study.
AID399959Increase in transformation frequency of tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as transgenic callus formation at 100 uM after 21 days2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID399958Increase in transformation frequency of tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as explant survival at 100 uM after 21 days2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID399955Toxicity in tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as mortality at 500 uM after 7 days2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID399956Toxicity in tobacco leaf explant co-cultured with Agrobacterium tumefaciens A348 assessed as mortality at 2 mM within 3 to 4 days2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
AID399946Induction of virH gene expression in Agrobacterium tumefaciens A348 overexpressing pSM219 virH::lacZ assessed as beta-galactosidase activity at 100 uM after 18 hrs2004Journal of natural products, Mar, Volume: 67, Issue:3
Effect of phenolic glycosides on Agrobacterium tumefaciens virH gene induction and plant transformation.
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.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
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.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (132)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (6.82)18.7374
1990's26 (19.70)18.2507
2000's39 (29.55)29.6817
2010's49 (37.12)24.3611
2020's9 (6.82)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.52

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

MetricThis Compound (vs All)
Research Demand Index47.52 (24.57)
Research Supply Index4.93 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index73.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (1.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other136 (98.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]