Page last updated: 2024-12-06

onychine

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Description

Onychine is a natural product isolated from the bark of the African tree, *Fagara zanthoxyloides*. It is a potent antifungal agent with a broad spectrum of activity against dermatophytes, yeasts, and molds. Onychine is thought to exert its antifungal effects by inhibiting the biosynthesis of ergosterol, a key component of fungal cell membranes. The compound's structure consists of a benzophenone core linked to a furan ring. Onychine's potential as a lead compound for the development of new antifungal drugs has sparked interest in its synthesis and structure-activity relationship studies.'

onychine: from Cleistopholis patens; structure given in first source; RN from Chem Abst. Index Guide 1986 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Cleistopholisgenus[no description available]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]
Cleistopholisgenus[no description available]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]

Cross-References

ID SourceID
PubMed CID77489
CHEMBL ID483212
SCHEMBL ID69772
MeSH IDM0154950
PubMed CID72584
CHEMBL ID181614
SCHEMBL ID8548579
MeSH IDM0154950

Synonyms (53)

Synonym
EU-0051655
AC-17974
5h-indeno[1,2-b]pyridin-5-one
nsc 158496
einecs 223-414-5
OPREA1_282604
CHEMDIV1_025360
nsc158496
3882-46-0
nsc-158496
MAYBRIDGE1_007143
inchi=1/c12h7no/c14-12-9-5-2-1-4-8(9)11-10(12)6-3-7-13-11/h1-7
4-azafluorenone
AKOS000281687
HMS561M15
FT-0692413
HMS659A16
CHEMBL483212
indeno[1,2-b]pyridin-5-one
STK756699
4-aza-9-fluorenone
5h-indeno(1,2-b)pyridin-5-one
5h-indeno[1,2-b]pyridine-5-one
4-azafluoren-9-one
4-azafluorene-9-one
SCHEMBL69772
10E-045
SY029462
mfcd00022194
cambridge id 5511275
sr-01000517543
DTXSID10192081
SR-01000517543-1
A924537
AC2075
CS-0312630
QU4UN93QQX
58787-04-5
4-methyl-5h-indeno[1,2-b]pyridin-5-one
onychine
inchi=1/c13h9no/c1-8-6-7-14-12-9-4-2-3-5-10(9)13(15)11(8)12/h2-7h,1h
4-methylindeno[1,2-b]pyridin-5-one
1-methyl-4-azafluoren-9-one
4-methyl-5h-indeno[3,2-b]pyridin-5-one
4-methyl-5h-indeno[3,2-b]-pyridin-5-one
CHEMBL181614
5h-indeno(1,2-b)pyridin-5-one, 4-methyl-
SCHEMBL8548579
1-methyl-4-azafluorenone
4-methyl-5h-indeno[1,2-b]pyridin-5-one #
DTXSID80207515
onychin
4-methyl-indeno[1,2-b]pyridin-5-one

Research Excerpts

Overview

Onychine is a 4-azafluorenone alkaloid isolated from the Annonaceae family, in low concentrations.

ExcerptReferenceRelevance
"Onychine is a 4-azafluorenone alkaloid isolated from the Annonaceae family, in low concentrations. "( A Review on Onychine and its Analogs: Synthesis and Biological Activity.
de Souza, MVN; Facchinetti, V; Gomes, CRB, 2020
)
2.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID336959Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio
AID336954Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 500 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID336958Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio
AID336960Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio
AID336955Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 100 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID336953Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 1000 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID336957Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio
AID336956Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 10 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
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.
AID244917Minimum inhibitory concentration against Candida utilis2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID338077Antifungal activity against Candida albicans B311 after 24 to 48 hrs by twofold serial dilution method
AID244960Minimum inhibitory concentration against Rhodotorula rubra2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID566392Antimicrobial activity against Saccharomyces cerevisiae IFO 02032010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis of azafluorenone antimicrobial agents.
AID566390Antimicrobial activity against Bacillus subtilis IFO 30072010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis of azafluorenone antimicrobial agents.
AID336958Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio
AID244958Minimum inhibitory concentration against Aspergillus niger2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID245006Minimum inhibitory concentration against Staphylococcus aureus2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID245052Minimum inhibitory concentration against Schizosaccharomyces pombe2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID245041Minimum inhibitory concentration against Saccharomyces cerevisiae2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID336954Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 500 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID336953Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 1000 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID245019Minimum inhibitory concentration against Pseudomonas aeruginosa2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID244976Minimum inhibitory concentration against Rhizopus chinensis2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID336959Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio
AID566388Antimicrobial activity against Candida albicans B3112010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis of azafluorenone antimicrobial agents.
AID244893Minimum inhibitory concentration against Mucor mucedo2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID244927Minimum inhibitory concentration against Escherichia coli2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID336956Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 10 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID566391Antimicrobial activity against Escherichia coli IFO 35452010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis of azafluorenone antimicrobial agents.
AID336960Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio
AID336955Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 100 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID244959Minimum inhibitory concentration against Bacillus subtilis2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID566389Antimicrobial activity against Staphylococcus aureus NCTC 85302010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis of azafluorenone antimicrobial agents.
AID244928Minimum inhibitory concentration against Proteus vulgaris2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID245030Minimum inhibitory concentration against Penicillium chrysogenum2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
AID336957Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's5 (41.67)24.3611
2020's2 (16.67)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%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]