Compounds > 4-phenylbutyl isothiocyanate
Page last updated: 2024-11-07

4-phenylbutyl isothiocyanate

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

Description

4-phenylbutyl isothiocyanate: structure given in first source; inhibits tumorigenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID124881
CHEMBL ID446473
CHEBI ID179058
SCHEMBL ID1526828
MeSH IDM0217680

Synonyms (23)

Synonym
4-isothiocyanatobutylbenzene
1-isothiocyanato-4-phenylbutane
CHEBI:179058
ccris 3148
4-phenylbutyl isothiocyanate
4-phenylbutylisolthiocyanate
61499-10-3
(4-isothiocyanatobutyl)benzene
phenylbutyl isothiocyanate
CHEMBL446473
AKOS006229428
4-phenylbutylisothiocyanate
FT-0619400
61449-10-3
SCHEMBL1526828
benzene, (4-isothiocyanatobutyl)-
DTXSID80210463
bdbm50073714
mfcd00052335
benzene,(4-isothiocyanatobutyl)-
(4-isothiocyanatobutyl)benzene, 9ci
Q67879620
MS-22004
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
organic amino compoundA compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Macrophage migration inhibitory factorHomo sapiens (human)IC50 (µMol)1.90000.03803.09109.8000AID1198788
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cytokine productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of mature B cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
inflammatory responseMacrophage migration inhibitory factorHomo sapiens (human)
cell surface receptor signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cell population proliferationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of gene expressionMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of protein kinase A signalingMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of macrophage chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
carboxylic acid metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cell migrationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of B cell proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of lipopolysaccharide-mediated signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of tumor necrosis factor productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of myeloid cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
regulation of macrophage activationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
innate immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of fibroblast proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of protein metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of prostaglandin secretion involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of myeloid leukocyte cytokine production involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
protein homotrimerizationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of arachidonic acid secretionMacrophage migration inhibitory factorHomo sapiens (human)
cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of chemokine (C-X-C motif) ligand 2 productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protease bindingMacrophage migration inhibitory factorHomo sapiens (human)
dopachrome isomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine receptor bindingMacrophage migration inhibitory factorHomo sapiens (human)
protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
chemoattractant activityMacrophage migration inhibitory factorHomo sapiens (human)
identical protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
phenylpyruvate tautomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
nucleoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytosolMacrophage migration inhibitory factorHomo sapiens (human)
plasma membraneMacrophage migration inhibitory factorHomo sapiens (human)
cell surfaceMacrophage migration inhibitory factorHomo sapiens (human)
vesicleMacrophage migration inhibitory factorHomo sapiens (human)
secretory granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular exosomeMacrophage migration inhibitory factorHomo sapiens (human)
ficolin-1-rich granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID412928Cytotoxicity against human T98G cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412927Cytotoxicity against human MDA-MB-231 cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID1198788Inhibition of macrophage migration inhibitory factor tautomerase activity in human Jurkat T cells using L-dopachrome methyl ester as substrate incubated for 30 mins prior to substrate addition measured for 2 mins by spectrophotometric analysis2015European journal of medicinal chemistry, Mar-26, Volume: 93Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor.
AID412940Cytotoxicity against human HT1080 cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412929Cytotoxicity against human PC-3 cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID681312TP_TRANSPORTER: increase in Vinblastine intracellular accumulation (Vinblastine: 0.05 uM, Phenylbutyl isothiocyanate: 100 uM) in PANC-1 cells2002Pharmaceutical research, Oct, Volume: 19, Issue:10
Effect of organic isothiocyanates on the P-glycoprotein- and MRP1-mediated transport of daunomycin and vinblastine.
AID412933Antiproliferative activity against human UACC-903 cells assessed as BrdU incorporation after 24 hrs by ELISA relative to control2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID692266Induction of apoptosis in human MDA-MB-231 cells expressing p53 R280K mutant at 10 uM incubated for 24 hrs by FITC/Annexin-V staining method2011Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3
Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships.
AID412934Induction of apoptosis in human UACC-903 cells assessed as increase in caspase 3 activity after 24 hrs relative to control2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412939Toxicity in human UACC-903 cells xenografted in Harlan Sprague-Dawley athymic nude mouse assessed as effect on body weight at 2.5 uM, ip administered three times per week2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID692256Induction of p53 R280K mutant depletion in human MDA-MB-231 cells at 10 uM by immunoblot analysis2011Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3
Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships.
AID412935Induction of apoptosis in human UACC-903 cells assessed as increase in caspase 7 activity after 24 hrs relative to control2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412937Antitumor activity in human UACC-903 cells xenografted in Harlan Sprague-Dawley athymic nude mouse assessed as reduction in tumor size at 2.5 uM, ip administered three times per week2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412930Cytotoxicity against human Caco-2 cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412936Antitumor activity in human UACC-903 cells xenografted in Harlan Sprague-Dawley athymic nude mouse assessed as reduction in tumor size at 0.76 uM, ip administered three times per week2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID412932Cytotoxicity against human UACC-903 cells assessed as decrease in cell viability after 24 hrs by MTS assay relative to control2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
AID692255Induction of p53 G245C mutant depletion in human NCI-H596 cells at 20 uM by immunoblot analysis2011Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3
Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships.
AID412931Cytotoxicity against human UACC-903 cells after 72 hrs by MTS assay2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (37.50)18.2507
2000's3 (37.50)29.6817
2010's2 (25.00)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: 12.22

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

MetricThis Compound (vs All)
Research Demand Index12.22 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.22)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzyl isothiocyanate
benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma		3.470benzenes;
isothiocyanate		antibacterial drug
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.4920isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
allyl isothiocyanate
allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.		2.4920alkenyl isothiocyanate;
isothiocyanate		antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
lachrymator;
metabolite
dimethylnitrosamine
Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.		1.9810nitrosaminegeroprotector;
mutagen
phenylisothiocyanate
phenylisothiocyanate: structure. phenyl isothiocyanate : An isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation.		2.7330isothiocyanateallergen;
reagent
1-naphthylisothiocyanate
1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.		2.0110isothiocyanateinsecticide
n-methylphenethylamine
N-methylphenethylamine: substrate for type A & B monoamine oxidase; RN given refers to parent cpd		2.0610
nitrosobenzylmethylamine
nitrosobenzylmethylamine: structure		1.9810
phenethyl isothiocyanate
phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.		3.470isothiocyanateantineoplastic agent;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
metabolite
benzyl thiocyanate
benzyl thiocyanate: increases activities of anhydrotetracycline oxygenase		2.1110thiocyanates
nitrosobis(2-oxopropyl)amine
nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).		710ketone;
nitrosamine		carcinogenic agent
3-phenylpropyl isothiocyanate
3-phenylpropyl isothiocyanate: structure given in first source		2.7330benzenes
erucin
[no description available]		2.0610isothiocyanate
4-(methylnitrosoamino)-4-(3-pyridyl)-1-butanol
4-(methylnitrosoamino)-4-(3-pyridyl)-1-butanol: tobacco-specific N-nitrosamine; structure given in first source		1.9810
6-phenylhexyl isothiocyanate
[no description available]		3.2760
phenylethyl isocyanate
2-phenylethyl isocyanate : An isocyanate having a 2-phenylethyl group attached to the nitrogen.		2.1110isocyanateshapten
acetyl-aspartyl-glutamyl-valyl-aspartal
acetyl-aspartyl-glutamyl-valyl-aspartal: a capase inhibitor. Ac-Asp-Glu-Val-Asp-H : A tetrapeptide consisting of two L-aspartic acid residues, an L-glutamyl residue and an L-valine residue with an acetyl group at the N-terminal and with the C-terminal carboxy group reduced to an aldehyde. It is an inhibitor of caspase-3/7.		1.9910tetrapeptideprotease inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Esophagus
[description not available]		01.9810
Esophageal Neoplasms
Tumors or cancer of the ESOPHAGUS.		01.9810
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		0210
Adenocarcinoma, Basal Cell
[description not available]		0210
Cancer of Kidney
[description not available]		0210
Experimental Hepatoma
[description not available]		0210
Cancer of Lung
[description not available]		0210
Experimental Neoplasms
[description not available]		0210
Cancer of Pancreas
[description not available]		0210
Carcinoma, Ductal, Pancreatic
[description not available]		0210
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		0210
Kidney Neoplasms
Tumors or cancers of the KIDNEY.		0210
Lung Neoplasms
Tumors or cancer of the LUNG.		0210
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		0210
Carcinoma, Pancreatic Ductal
Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.		0210