Page last updated: 2024-11-12

trans-avicennol

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Description

trans-avicennol: from Zanthoxylum chiloperone var. angustifolium; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
ZanthoxylumgenusA plant genus of the family RUTACEAE. Some members of Zanthoxylum are reclassified from ELEUTHEROCOCCUS, Melicope, and EVODIA. The twigs are used as dental brushing sticks (TOOTHBRUSHING). Most plants that are called Fagara have been reclassified as Zanthoxylum, however some Fagara were reclassified to MELICOPE (also in the Rutacea family) or to GLEDITSIA (a genus in the FABACEAE family).[MeSH]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID15118768
CHEMBL ID258230
MeSH IDM0572858

Synonyms (6)

Synonym
6-[(e)-3-hydroxy-3-methyl-but-1-enyl]-5-methoxy-2,2-dimethyl-pyrano[2,3-h]chromen-8-one
avicennol
trans-avicennol
CHEMBL258230
bdbm50379307
6-[(e)-3-hydroxy-3-methylbut-1-enyl]-5-methoxy-2,2-dimethylpyrano[2,3-h]chromen-8-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 12Homo sapiens (human)Ki0.77000.00021.10439.9000AID729559
Carbonic anhydrase 1Homo sapiens (human)Ki8.46000.00001.372610.0000AID729563
Carbonic anhydrase 2Homo sapiens (human)Ki100.00000.00000.72369.9200AID729562
Indoleamine 2,3-dioxygenase 1Homo sapiens (human)Ki635.00000.09402.37907.0000AID654894
Carbonic anhydrase 7Homo sapiens (human)Ki8.98000.00021.37379.9000AID729561
Carbonic anhydrase 9Homo sapiens (human)Ki0.78000.00010.78749.9000AID729560
Carbonic anhydrase 13Homo sapiens (human)Ki29.30000.00031.23099.8000AID729558
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
regulation of activated T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell tolerance inductionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of chronic inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of type 2 immune responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
female pregnancyIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic process to kynurenineIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
response to lipopolysaccharideIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of interleukin-10 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of interleukin-12 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
multicellular organismal response to stressIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
kynurenic acid biosynthetic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
swimming behaviorIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
'de novo' NAD biosynthetic process from tryptophanIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 7Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 7Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 7Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 7Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 7Homo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
electron transfer activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
heme bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
indoleamine 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
metal ion bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 13Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 13Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
cytosolIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
smooth muscle contractile fiberIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
stereocilium bundleIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
cytoplasmIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
cytosolCarbonic anhydrase 7Homo sapiens (human)
cytoplasmCarbonic anhydrase 7Homo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
cytosolCarbonic anhydrase 13Homo sapiens (human)
myelin sheathCarbonic anhydrase 13Homo sapiens (human)
intracellular membrane-bounded organelleCarbonic anhydrase 13Homo sapiens (human)
cytoplasmCarbonic anhydrase 13Homo sapiens (human)
cytosolCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID729563Inhibition of human carbonic anhydrase 1 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
AID654890Antiproliferative activity against human TG10 cells at 34.2 ug/ml by WST-1 assay2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID654889Antiproliferative activity against human TG1 cells at 34.2 ug/ml by WST-1 assay2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID729559Inhibition of human carbonic anhydrase 12 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
AID654892Induction of Erk phosphorylation in human TG1 cells at 100 uM after 30 mins by Western blot analysis2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID654891Antiproliferative activity against human NSC-24 cells at 34.2 ug/ml to 100 uM by WST-1 assay2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID404141Antifungal activity against Aspergillus fumigatus 04-4862005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID404137Antifungal activity against Candida albicans ATCC 102312005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID729561Inhibition of human carbonic anhydrase 7 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
AID404138Antifungal activity against Cryptococcus neoformans H992005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID404139Antifungal activity against Saccharomyces cerevisiae ATCC 26.012005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID654893Inhibition of Erk phosphorylation in human NSC-24 cells at 100 uM after 30 mins by Western blot analysis2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID729558Inhibition of human carbonic anhydrase 13 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
AID328636Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced elastase release2008Journal of natural products, Feb, Volume: 71, Issue:2
Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae.
AID328635Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced superoxide anion generation2008Journal of natural products, Feb, Volume: 71, Issue:2
Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae.
AID654894Competitive inhibition of human indoleamine 2,3-dioxygenase assessed as conversion of N-formylkynurenine to kynurenine after 2 hrs by spectrophotometrical analysis2012Journal of natural products, Feb-24, Volume: 75, Issue:2
Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells.
AID729560Inhibition of human carbonic anhydrase 9 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
AID404140Antifungal activity against Trichophyton mentagrophytes var. interdigitale CPCM 06.992005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID729562Inhibition of human carbonic anhydrase 2 preincubated for 6 hrs by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Natural product coumarins that inhibit human carbonic anhydrases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (40.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]