CAPSAICIN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC M02AB01 N01BX04
UNII S07O44R1ZM
EPA CompTox DTXSID9020241

Structure

InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N
Smiles COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChI
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H27NO3
Molecular Weight 305.42
AlogP 3.79
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 58.56
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Vanilloid receptor opener OPENER FDA Wikipedia
Protein: Vanilloid receptor
Description: Transient receptor potential cation channel subfamily V member 1
Organism : Homo sapiens
Q8NER1 ENSG00000196689
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - -7-11
Enzyme Ligase
- - - 42000 -
Enzyme Oxidoreductase
- 3800 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 29000 - - -
Ion channel Voltage-gated ion channel Transient receptor potential channel
3-30200 8-8 - 1700-2000 -
Assay Description Organism Bioactivity Reference
Increased [Ca2+] influx into Dorsal Root Ganglion(DRG) neurons None 300.0 nM
In vitro effective dose for contraction of guinea pig ileum Cavia porcellus 260.0 nM
Effective concentration for guinea pig ileum contraction in an in vitro assay Cavia porcellus 260.0 nM
In vitro contraction in guinea pig ileum equivalent to 50% capsaicin response Cavia porcellus 260.0 nM
Compound tested in vitro for [Ca2+] influx into neonatal rat dorsal root ganglia (DRG) None 300.0 nM
Effective concentration for [Ca2+] uptake into dorsal root ganglia neurones in rat cultured spinal sensory neurones Rattus norvegicus 300.0 nM
In vitro agonist activity against [Ca2+] uptake in neonatal rat cultured spinal sensory neurons Rattus norvegicus 300.0 nM
In vitro effective concentration for [Ca2+] uptake and accumulation of [Ca2+] in neonatal rat cultured spinal sensory neurons Rattus norvegicus 300.0 nM
In vitro effective concentration for [Ca2+] uptake into dorsal root ganglia neurones in culture None 300.0 nM In vitro effective concentration for [Ca2+] uptake into dorsal root ganglia neurones in culture None 300.0 nM
In vitro agonist activity, increased [Ca2+] influx, at vanilloid receptor of rat dorsal root ganglia Rattus norvegicus 30.0 nM
In vitro [Ca2+] influx relative to capsaicin by Rat Vanilloid receptor (VR1) expressing CHO cells Rattus norvegicus 44.8 nM
Concentration necessary to induce a relative half-maximal response measured by the entry of [Ca2+] into human embryonic kidney HEK293 cells overexpressing the human VR1 None 19.95 nM
Agonist activity at human recombinant TRPV1 expressed in human HEK293 cells Homo sapiens 40.0 nM
Agonist activity at rat TRPV1 receptor expressed in CHO cells assessed as calcium uptake Rattus norvegicus 44.8 nM
Agonist activity at human recombinant TRPV1 expressed in HEK293 cells assessed as increase in intracellular calcium level Homo sapiens 20.0 nM
Inhibition of HSL in Wistar rat isolated fat cells at 10 uM by spectrophotometric assay Rattus norvegicus 33.0 %
Agonist activity at human TRPV1 expressed in HEK293 cells assessed as increase in intracellular calcium level Homo sapiens 40.0 nM
Agonist activity at human TRPV1 expressed in tetracycline-stimulated HEK293 cells assessed as increase in intracellular calcium levels by fluorimetric assay Homo sapiens 2.512 nM
Binding affinity to human recombinant TRPV1 Homo sapiens 6.0 nM
Binding affinity to rat TRPV1 Rattus norvegicus 19.0 nM
Agonist activity at human TRPV1 ion channel expressed in HEK293 cells assessed as calcium influx by fluo-4-Am-based fluorimetry Homo sapiens 3.9 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus -6.53 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 6.29 %
Inhibition of Electrophorus electricus (electric eel) acetylcholinesterase (AChE) using acetylcholine iodide as substrate at 10 '-4 M by Ellman method Electrophorus electricus 11.4 %
Inhibition of Escherichia coli GR19N NDH2 assessed as deaminoNADH-DB reductase activity at 100 uM relative to control Escherichia coli 20.0 %
Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay Homo sapiens 20.0 %
Agonist activity at human recombinant TRPV1 expressed in HEK293 cells assessed as Ca2+ influx by Fluo-4 dye based assay Homo sapiens 5.3 nM
Antagonist activity against human recombinant TRPV1 expressed in HEK293 cells assessed as inhibition of capsaicin-induced Ca2+ influx pre-treated 5 mins before capsaicin addition by Fluo-4 dye based assay Homo sapiens 8.0 nM
Agonist activity at recombinant TRPV1 (unknown origin) expressed in HEK293 cells assessed as induction of calcium flux administered for 1 min followed by compound washout via perfusion for 1 min by FURA-2AM-dye based fluorescence assay Homo sapiens 870.0 nM Agonist activity at recombinant TRPV1 (unknown origin) expressed in HEK293 cells assessed as induction of calcium flux administered for 1 min followed by compound washout via perfusion for 1 min by FURA-2AM-dye based fluorescence assay Homo sapiens 870.96 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 1.12 %
Antitumor activity against human Aspc-1 cells xenografted in athymic nude mouse assessed as reduction in tumor volume at 5 mg/kg after 35 days relative to control Homo sapiens 73.0 %
Agonist activity at human TRPV1 expressed in CHO cells assessed as increase in 45Ca2+ uptake incubated for 5 mins by liquid scintillation counting method Homo sapiens 25.9 nM
Agonist activity at rat TRPV1 expressed in CHO cells assessed as increase in 45Ca2+ uptake incubated for 5 mins by liquid scintillation counting method Rattus norvegicus 44.8 nM
Agonist activity at human TRPV1 expressed in HEK293T cells assessed as increase in Ca2+ transport incubated for 5 mins by calcium-5 fluorescence dye-based FLIPR assay Homo sapiens 7.2 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 26.63 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 %
Agonist activity at human TRPV1 stably transfected in HEK293 cells assessed as increase in calcium influx in presence of ionomycin by Fluo-4-AM dye based spectrofluorimetric method Homo sapiens 5.3 nM
Antagonist activity at human TRPV1 stably transfected in HEK293 cells assessed as decrease in calcium influx preincubated for 5 mins followed by capsaicin addition by Fluo-4-AM dye based spectrofluorimetric method Homo sapiens 8.0 nM
Inhibition of human serum BChE at 100 uM using butyrylthiocholineiodide as substrate preincubated for 20 mins followed by substrate addition by Ellman's method relative to control Homo sapiens 20.0 %
Agonist activity at human TRPV1 expressed in CHO cells assessed as stimulation of calcium uptake by 45Ca2+ uptake assay Homo sapiens 44.8 nM

Related Entries

Cross References

Resources Reference
ChEBI 3374
ChEMBL CHEMBL294199
DrugBank DB06774
DrugCentral 3064
FDA SRS S07O44R1ZM
Human Metabolome Database HMDB0002227
Guide to Pharmacology 2486
KEGG C06866
PDB 4DY
PubChem 1548943
SureChEMBL SCHEMBL8085
ZINC ZINC000001530575
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