5-(nonyloxy)tryptamine: a 5-HT1D beta serotonin receptor agonist; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
5-nonyloxytryptamine : A tryptamine derivative that consists of serotonin bearing an additional O-nonyl substituent. 5-HT1B selective agonist, several times more potent than sumatriptan and inactive as a 5-HT1A agonist (Ki at 5-HT1B = 1 nM, selectivity over 5-HT1A > 300-fold). [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]
| ID Source | ID |
|---|---|
| PubMed CID | 1797 |
| CHEMBL ID | 97450 |
| CHEBI ID | 64149 |
| SCHEMBL ID | 2335932 |
| MeSH ID | M0235408 |
| Synonym |
|---|
| CHEMBL97450 , |
| chebi:64149 , |
| bdbm50039947 |
| 2-(5-nonyloxy-1h-indol-3-yl)-ethylamine |
| unii-tv6chd9vpt |
| 5-(nonyloxy)-1h-indole-3-ethanamine |
| 1h-indole-3-ethanamine, 5-(nonyloxy)- |
| tv6chd9vpt , |
| BRD-K08219523-001-01-9 |
| 5-(nonyloxy)-tryptamine |
| gtpl106 |
| NCGC00024858-01 , |
| tocris-0901 |
| BPBIO1_000133 |
| BIOMOL-NT_000115 |
| 5-nonyloxytryptamine |
| 5-(nonyloxy)tryptamine |
| NCGC00024858-02 |
| L000965 |
| 157798-12-4 |
| 2-(5-nonoxy-1h-indol-3-yl)ethanamine |
| 3-(2-aminoethyl)-5-nonyloxyindole |
| 2-[5-(nonyloxy)-1h-indol-3-yl]ethanamine |
| o-nonylserotonin |
| SCHEMBL2335932 |
| DTXSID4058653 |
| Q4639557 |
| BRD-K08219523-034-01-0 |
| PD047537 |
| Role | Description |
|---|---|
| serotonergic agonist | An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders. |
| [role 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] | |
| Class | Description |
|---|---|
| tryptamines | Tryptamine and its substitution derivatives. |
| primary amino compound | A compound formally derived from ammonia by replacing one hydrogen atom by an organyl group. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 22.3872 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 25.1189 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| Chain A, Ferritin light chain | Equus caballus (horse) | Potency | 25.1189 | 5.6234 | 17.2929 | 31.6228 | AID485281 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 47.3935 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| USP1 protein, partial | Homo sapiens (human) | Potency | 15.8489 | 0.0316 | 37.5844 | 354.8130 | AID504865 |
| TDP1 protein | Homo sapiens (human) | Potency | 8.3407 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 31.0989 | 0.1800 | 13.5574 | 39.8107 | AID1460 |
| 67.9K protein | Vaccinia virus | Potency | 22.3872 | 0.0001 | 8.4406 | 100.0000 | AID720580 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 15.8489 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| cytochrome P450 2D6 isoform 1 | Homo sapiens (human) | Potency | 25.1189 | 0.0020 | 7.5337 | 39.8107 | AID891 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 12.4435 | 31.6228 | AID902; AID924 |
| cytochrome P450 2C19 precursor | Homo sapiens (human) | Potency | 10.0000 | 0.0025 | 5.8400 | 31.6228 | AID899 |
| cytochrome P450 2C9 precursor | Homo sapiens (human) | Potency | 25.1189 | 0.0063 | 6.9043 | 39.8107 | AID883 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 57.4571 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 31.6228 | 0.0398 | 16.7842 | 39.8107 | AID995 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 21.1546 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 2.2387 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 39.8107 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 29.9033 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 2.5119 | 0.0200 | 10.7869 | 31.6228 | AID912 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Polyunsaturated fatty acid lipoxygenase ALOX15B | Homo sapiens (human) | Potency | 12.5893 | 0.3162 | 12.7657 | 31.6228 | AID881 |
| Integrin beta-3 | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Integrin alpha-IIb | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 20.1071 | 0.0063 | 8.2350 | 39.8107 | AID881; AID883 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1A | Homo sapiens (human) | Ki | 0.3150 | 0.0001 | 0.5326 | 10.0000 | AID3829 |
| 5-hydroxytryptamine receptor 2C | Rattus norvegicus (Norway rat) | Ki | 0.2700 | 0.0002 | 0.6677 | 10.0000 | AID5729 |
| 5-hydroxytryptamine receptor 1D | Homo sapiens (human) | Ki | 0.0160 | 0.0001 | 0.8087 | 10.0000 | AID4910 |
| 5-hydroxytryptamine receptor 1B | Homo sapiens (human) | Ki | 0.0012 | 0.0001 | 0.5485 | 9.2100 | AID4929 |
| 5-hydroxytryptamine receptor 2A | Homo sapiens (human) | Ki | 0.2600 | 0.0000 | 0.3855 | 10.0000 | AID5201 |
| 5-hydroxytryptamine receptor 3A | Rattus norvegicus (Norway rat) | Ki | 1.0000 | 0.0002 | 0.4841 | 10.0000 | AID5878 |
| 5-hydroxytryptamine receptor 3B | Rattus norvegicus (Norway rat) | Ki | 1.0000 | 0.0002 | 0.5023 | 10.0000 | AID5878 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1D | Homo sapiens (human) | ED50 | 0.0680 | 0.0680 | 0.1925 | 0.3170 | AID4583 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1508630 | Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 2021 | Cell reports, 04-27, Volume: 35, Issue:4 | A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. |
| AID1347154 | Primary screen GU AMC qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID5729 | Binding affinity was measured on 5-hydroxytryptamine 2C receptor in J1 cells transfected with rat 5-HT2C gene labeled with [3H]mesulergine | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID5878 | Binding affinity was measured on 5-hydroxytryptamine 3 receptor in NG-108 cells labeled with [3H]GR-65630 | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID4583 | Compound was evaluated for its agonistic activity on 5-hydroxytryptamine 1D receptor | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID4910 | Binding affinity was measured on 5-hydroxytryptamine 1D receptor alpha in COS cells transfected with human 5-HT1D alpha gene labeled with [3H]5-HT | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID5201 | Binding affinity was measured on 5-hydroxytryptamine 2A receptor in GF6 cells transfected with human 5-HT2A gene labeled with [3H]ketanserin | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID4929 | Binding affinity was measured on 5-hydroxytryptamine 1D receptor beta in CHO cells transfected with human 5-HT1D beta gene labeled with [3H]5-HT | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID3829 | Binding affinity was measured on 5-hydroxytryptamine 1A receptor in AK cells transfected with human 5-HT1A gene labeled with [3H]-8-OH-DPAT | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID4698 | Binding affinity was measured on 5-hydroxytryptamine 1B receptor in rat striatum labeled with [3H]5-HT | 1994 | Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18 | 5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist. |
| AID1346264 | Human 5-HT1B receptor (5-Hydroxytryptamine receptors) | 1999 | European journal of pharmacology, Sep-10, Volume: 380, Issue:2-3 | Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor. |
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal 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. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 3 (33.33) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 3 (33.33) | 24.3611 |
| 2020's | 3 (33.33) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.00) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||