Xanthoxyline is a natural compound isolated from the bark of the Zanthoxylum genus of plants, commonly known as prickly ash. It is a potent inhibitor of acetylcholinesterase, an enzyme involved in the breakdown of acetylcholine, a neurotransmitter crucial for muscle contraction and memory function. This inhibitory action has been studied for its potential therapeutic applications in treating Alzheimer's disease and other cognitive impairments. Xanthoxyline has also shown antimicrobial activity against various bacteria, including Staphylococcus aureus, suggesting its potential for developing new antibiotic agents. While more research is needed to fully understand its efficacy and safety, xanthoxyline shows promise as a lead compound for the development of novel therapeutic agents.'
xanthoxyline: isolated from Sebastiania schottiana (Euphorbiaceae); structure given in first source; also present in Xanthoxylum, Rutaceae, Artemisia and other plants [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Artemisia | genus | A plant genus of the family ASTERACEAE with strong-smelling foliage. It is a source of SANTONIN and other cytotoxic TERPENES.[MeSH] | Asteraceae | A large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH] |
| Rutaceae | family | A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH] | Rutaceae | A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH] |
| Sebastiania | genus | [no description available] | Euphorbiaceae | The spurge family of flowering plants in the order Malpighiales. The family consists of annual and perennial herbs and woody shrubs or trees. Members contain securinine.[MeSH] |
| Sebastiania schottiana | species | [no description available] | Euphorbiaceae | The spurge family of flowering plants in the order Malpighiales. The family consists of annual and perennial herbs and woody shrubs or trees. Members contain securinine.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 66654 |
| CHEMBL ID | 450288 |
| CHEBI ID | 10070 |
| SCHEMBL ID | 44708 |
| MeSH ID | M0177367 |
| Synonym |
|---|
| smr001306755 |
| MLS002207182 |
| BRD-K12260308-001-02-6 |
| acetophenone, 2'-hydroxy-4',6'-dimethoxy- |
| ethanone, 1-(2-hydroxy-4,6-dimethoxyphenyl)- |
| DIVK1C_006809 |
| SDCCGMLS-0066937.P001 |
| SPECTRUM_000577 |
| SPECTRUM5_000237 |
| acetophenone,6'-dimethoxy- |
| 4,6-dimethoxy-2-hydroxyacetophenone |
| 2,4-di-o-methylphloroacetophenone |
| 2-hydroxy-4,6-dimethoxyacetophenone |
| nsc17392 |
| nsc-17392 |
| brevifolin |
| phloracetophenone dimethyl ether |
| phloroacetophenone 2,4-dimethyl ether |
| 2'-hydroxy-4',6'-dimethoxyacetophenone |
| brevifolin (zanthoxylum) |
| xanthoxyline |
| acetophenone der. |
| 1-(2-hydroxy-4,6-dimethoxy-phenyl)ethanone |
| BSPBIO_001701 |
| AQ-358/42007313 |
| 1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone |
| 90-24-4 |
| xanthoxylin |
| 2'-hydroxy-4',6'-dimethoxyacetophenone, 97% |
| NCGC00095824-01 |
| KBIO3_001201 |
| KBIOSS_001057 |
| KBIO1_001753 |
| KBIO2_003625 |
| KBIO2_001057 |
| KBIO2_006193 |
| KBIOGR_002137 |
| SPECTRUM2_000463 |
| SPECTRUM4_001499 |
| SPBIO_000566 |
| SPECPLUS_000713 |
| SPECTRUM3_000181 |
| SPECTRUM200441 |
| NCGC00095824-02 |
| chebi:10070 , |
| CHEMBL450288 |
| 4',6'-dimethoxy-2'-hydroxyacetophenone |
| D2683 |
| A843476 |
| 1-acetyl-2-hydroxy-4,6-dimethoxybenzene |
| unii-z8rsy5tzpa |
| nsc 17392 |
| einecs 201-978-3 |
| 1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one |
| brevifolin (van) |
| ai3-26010 |
| z8rsy5tzpa , |
| CCG-38702 |
| FT-0612544 |
| AKOS015856339 |
| S4781 |
| SCHEMBL44708 |
| 2'-hyroxy-4',6'-dimethoxyacetophenone |
| (2-hydroxy-4,6-dimethoxy-phenyl)-ethanone |
| xanthoxyline [who-dd] |
| xanthoxylin [mi] |
| 2-acetyl-3,5-dimethoxyphenol |
| 2',4'-dimethoxy-6'-hydroxyacetophenone |
| phloroacetophenone dimethyl ether |
| AC-35124 |
| 2-hydroxyl-4,6-dimethoxy-acetophenone |
| 1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone # |
| DTXSID10237981 |
| mfcd00017243 |
| SR-05000002434-1 |
| sr-05000002434 |
| 1-(2-hydroxy-4,6-dimethoxyphenyl)-ethanone |
| acetophenone, 2'-hydroxy-4',6'-dimethoxy- (8ci) |
| 2'-hydroxy-4',6'-dimethoxy-acetophenone |
| 2-hydroxy-4, 6-dimethoxyacetophenone |
| 4, 6-dimethoxy-2-hydroxyacetophenone |
| 6-methoxypaeonol |
| HY-N1063 |
| AS-40799 |
| ethanone,1-(2-hydroxy-4,6-dimethoxyphenyl)- |
| Q18210424 |
| BRD-K12260308-001-04-2 |
| CS-0016347 |
| 1-(2-hydroxy-4,6-dimethylphenyl)-ethanone |
| SY048579 |
| 2 inverted exclamation mark -hydroxy-4 inverted exclamation mark ,6 inverted exclamation mark -dimethoxyacetophenone |
| EN300-6477862 |
| Z1255434817 |
Xanthoxyline was found to be a potent inhibitor of spontaneous contractions of the circular smooth muscle layer of the dog ureter.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Xanthoxyline was found to be a potent inhibitor of spontaneous contractions of the circular smooth muscle layer of the dog ureter, yielding an IC50 of 54 microM." | ( Action of 2-hydroxy-4,6-dimethoxyacetophenone isolated from Sebastiania schottiana. Calixto, JB; Miguel, OG; Rae, GA; Yunes, RA, 1990) | 1 |
| Class | Description |
|---|---|
| carboxylic ester | An ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| USP1 protein, partial | Homo sapiens (human) | Potency | 1.1220 | 0.0316 | 37.5844 | 354.8130 | AID504865 |
| TDP1 protein | Homo sapiens (human) | Potency | 14.2610 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 28.1838 | 0.0398 | 16.7842 | 39.8107 | AID1454 |
| ubiquitin carboxyl-terminal hydrolase 2 isoform a | Homo sapiens (human) | Potency | 15.8489 | 0.6561 | 9.4520 | 25.1189 | AID927 |
| serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 26.6795 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
| geminin | Homo sapiens (human) | Potency | 0.2060 | 0.0046 | 11.3741 | 33.4983 | AID624297 |
| survival motor neuron protein isoform d | Homo sapiens (human) | Potency | 0.8913 | 0.1259 | 12.2344 | 35.4813 | AID1458 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 25.1189 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Disintegrin and metalloproteinase domain-containing protein 17 | Homo sapiens (human) | Potency | 15.8489 | 1.5849 | 13.0043 | 25.1189 | AID927 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1537670 | Cytotoxicity against human U937 cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID1537672 | Cytotoxicity against human MIAPaCa2 cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID381256 | Cytotoxicity against human 9KB cells assessed as cell survival at 100 ug/ml relative to control | |||
| AID510837 | Cytotoxicity against human HeLa cells after 72 hrs by XTT assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation. |
| AID510840 | Cytotoxicity against human HL60 cells after 72 hrs by XTT assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation. |
| AID1537674 | Cytotoxicity against human HCT116 cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID381257 | Cytotoxicity against human 9KB cells assessed as cell survival at 10 ug/ml relative to control | |||
| AID1537673 | Cytotoxicity against human REH cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID510839 | Cytotoxicity against human HT-29 cells after 72 hrs by XTT assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation. |
| AID1537671 | Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID1537669 | Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by alamar blue assay | 2019 | MedChemComm, Aug-01, Volume: 10, Issue:8 | The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery. |
| AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID510838 | Cytotoxicity against human A549 cells after 72 hrs by XTT assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal 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. |
| AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature 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] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 5 (20.83) | 18.2507 |
| 2000's | 6 (25.00) | 29.6817 |
| 2010's | 10 (41.67) | 24.3611 |
| 2020's | 3 (12.50) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 moderate demand-to-supply ratio for research on this compound.
| This Compound (28.60) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (4.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 24 (96.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||