Compounds > 5-fluoroindole
Page last updated: 2024-12-06

5-fluoroindole

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

5-Fluoroindole is a heterocyclic compound that serves as an important building block in the synthesis of various pharmaceutical compounds. It is commonly used as a precursor to indole-based drugs, which are known for their diverse therapeutic applications. 5-Fluoroindole has also been investigated for its potential antitumor activity. The synthesis of 5-fluoroindole typically involves the reaction of 5-fluoroaniline with a suitable electrophile, such as glyoxal or formaldehyde. Researchers study 5-fluoroindole due to its versatility as a synthetic intermediate and its potential for developing new therapeutic agents.'

Cross-References

ID SourceID
PubMed CID67861
CHEMBL ID555457
CHEBI ID72818
SCHEMBL ID228554
MeSH IDM0250385

Synonyms (47)

Synonym
5-fluoroindole ,
nsc88613
nsc-88613
399-52-0
BIDD:GT0536
1h-indole, 5-fluoro-
indole, 5-fluoro-
5-fluoroindole, 98%
5-fluoroindole, purum, >=97.0% (gc)
F-4525
inchi=1/c8h6fn/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10
F-4520
AC-2259
bdbm50294170
5-fluoro-1h-indole
14o ,
chebi:72818 ,
CHEMBL555457 ,
F0369
AKOS004117075
5-fluoro-1h-indole;indole, 5-fluoro-
A22152
5-fluoro indole
EN300-73560
nsc 88613
zl8w3fgt5k ,
einecs 206-917-4
unii-zl8w3fgt5k
AB00483
AM972
FT-0620421
SCHEMBL228554
3FUF
5-fluoro-indol
5-fluoroindol
5-fluoro-indole
5-fluoro-1h-indole #
mfcd00005671
DTXSID10192940
CS-D0680
SY003931
Q27140165
1-(3-nitro-phenyl)-piperazinedihydrochloride
AS-12602
BCP09868
HY-40156
Z1160902020
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
fluoroindoleAn organofluorine compound that is a compound based on an indole skeleton, containing one or more fluorine atoms.
[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 (18)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Chain A, Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)2,000.0000212.00001,235.33332,000.0000AID977608
Leukotriene A-4 hydrolaseHomo sapiens (human)IC50 (µMol)1,500.00000.00051.28547.6500AID420374; AID420375
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
proteolysisLeukotriene A-4 hydrolaseHomo sapiens (human)
lipid metabolic processLeukotriene A-4 hydrolaseHomo sapiens (human)
response to zinc ionLeukotriene A-4 hydrolaseHomo sapiens (human)
leukotriene biosynthetic processLeukotriene A-4 hydrolaseHomo sapiens (human)
protein metabolic processLeukotriene A-4 hydrolaseHomo sapiens (human)
peptide catabolic processLeukotriene A-4 hydrolaseHomo sapiens (human)
response to peptide hormoneLeukotriene A-4 hydrolaseHomo sapiens (human)
type I pneumocyte differentiationLeukotriene A-4 hydrolaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
RNA bindingLeukotriene A-4 hydrolaseHomo sapiens (human)
aminopeptidase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
epoxide hydrolase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
leukotriene-A4 hydrolase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
protein bindingLeukotriene A-4 hydrolaseHomo sapiens (human)
peptidase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
zinc ion bindingLeukotriene A-4 hydrolaseHomo sapiens (human)
tripeptide aminopeptidase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
metalloaminopeptidase activityLeukotriene A-4 hydrolaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
extracellular regionLeukotriene A-4 hydrolaseHomo sapiens (human)
nucleoplasmLeukotriene A-4 hydrolaseHomo sapiens (human)
cytosolLeukotriene A-4 hydrolaseHomo sapiens (human)
extracellular exosomeLeukotriene A-4 hydrolaseHomo sapiens (human)
tertiary granule lumenLeukotriene A-4 hydrolaseHomo sapiens (human)
ficolin-1-rich granule lumenLeukotriene A-4 hydrolaseHomo sapiens (human)
cytosolLeukotriene A-4 hydrolaseHomo sapiens (human)
nucleusLeukotriene A-4 hydrolaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID420376Inhibition of ionomycin-stimulated LTB4 production in human whole blood treated 15 mins prior to ionomycin challenge measured after 30 mins of stimulation by enzyme-linked immunosorbent assay2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.
AID420374Inhibition of peptidase activity of human recombinant LTA4H expressed in Escherichia coli BL21-AI/pRARE2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.
AID420373Solubility in methanol2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.
AID420375Inhibition of hydrolase activity of human recombinant LTA4H expressed in Escherichia coli BL21-AI/pRARE assessed as LTB4 formation by tandem quadrupole mass spectrometry2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Discovery of leukotriene A4 hydrolase inhibitors using metabolomics biased fragment crystallography.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (20.00)18.2507
2000's4 (40.00)29.6817
2010's4 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.74

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.

MetricThis Compound (vs All)
Research Demand Index30.74 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index33.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.74)

All Compounds (24.57)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
indole
[no description available]		2.0110indole;
polycyclic heteroarene		Escherichia coli metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		2.0110antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		2.7230erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
5-fluorotryptophan
5-fluorotryptophan: RN given refers to cpd with unspecified isomeric designation. 5-fluorotryptophan : A non-proteinogenic alpha-amino acid that is tryptophan in which the hydrogen at position 5 on the indole ring is replaced by a fluoro group.		2.4220non-proteinogenic alpha-amino acid;
organofluorine compound;
tryptophan derivative
4-fluorophenol
4-fluorophenol: structure given in first source. 4-fluorophenol : A fluorophenol that is phenol in which the hydrogen para- to the hydroxy group has been replaced by a fluorine.		2.1310fluorophenol;
monofluorobenzenes
5-hydroxyindole
[no description available]		2.0510hydroxyindoleshuman metabolite
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.7630diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
ubenimex
ubenimex: growth inhibitor		2.0510
5-chloroindole
5-chloroindole: a positive allosteric modulator of the 5-HT3 receptor		2.0510
dihydroresveratrol
dihydroresveratrol: structure in first source. dihydroresveratrol : A stilbenol that is 1,1'-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4'.		2.0510stilbenolplant metabolite;
xenobiotic metabolite
4-(2-Amino-1,3-thiazol-4-yl)phenol
[no description available]		2.0510phenols
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		2.0510resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
mocetinostat
mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).		2.110aminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline		antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent
ConditionIndicatedRelationship StrengthStudiesTrials
Depression, Involutional
Form of depression in those MIDDLE AGE with feelings of ANXIETY.		02.110
Innate Inflammatory Response
[description not available]		02.110
Cardiovascular Diseases
Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.		02.110
Depressive Disorder, Major
Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)		02.110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.110