Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:01 UTC |
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Update date | 2019-11-26 03:06:17 UTC |
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Primary ID | FDB012158 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Serotonin |
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Description | Serotonin, also known as enteramine or 5-HT, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. Serotonin is a very strong basic compound (based on its pKa). Serotonin exists in all living organisms, ranging from bacteria to humans. Serotonin is found, on average, in the highest concentration within a few different foods, such as sea-buckthornberries, common walnuts, and oats and in a lower concentration in green beans, red bell peppers, and swiss chards. Serotonin has also been detected, but not quantified in, several different foods, such as grapes, cocoa beans, pepper (c. frutescens), avocado, and common pea. This could make serotonin a potential biomarker for the consumption of these foods. Serotonin, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, schizophrenia, parkinson's disease, and hypothyroidism; serotonin has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. |
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CAS Number | 50-67-9 |
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Structure | |
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Synonyms | Synonym | Source |
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3-(2-Aminoethyl)-1H-indol-5-ol | ChEBI | 5-HT | ChEBI | 5-Hydroxytryptamine | ChEBI | Enteramine | ChEBI | Serotonine | ChEBI | Thrombocytin | ChEBI | Thrombotonin | ChEBI | Hippophaine | HMDB | Hydroxytryptamine | HMDB | 5 Hydroxytryptamine | HMDB | 3-(2-Aminoethyl)indol-5-ol | HMDB | 3-(b-Aminoethyl)-5-hydroxyindole | HMDB | 5-HTA | HMDB | 5-Hydroxy-3-(b-aminoethyl)indole | HMDB | 5-Hydroxy-tryptamine | HMDB | 5-Hydroxyltryptamine | HMDB | 5-Hydroxytriptamine | HMDB | Antemovis | HMDB | DS Substance | HMDB | Enteramin | HMDB | 3-(2-Aminoethyl)-1H-indol-5-ol, 9CI | db_source | 3-(2-Aminoethyl)-5-hydroxyindole | db_source | 5HT | db_source | Anthemovister | db_source | DS substance | HMDB | Serotonin | db_source |
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Predicted Properties | |
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Chemical Formula | C10H12N2O |
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IUPAC name | 3-(2-aminoethyl)-1H-indol-5-ol |
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InChI Identifier | InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2 |
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InChI Key | QZAYGJVTTNCVMB-UHFFFAOYSA-N |
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Isomeric SMILES | NCCC1=CNC2=CC=C(O)C=C12 |
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Average Molecular Weight | 176.2151 |
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Monoisotopic Molecular Weight | 176.094963016 |
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Classification |
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Description | Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Tryptamines and derivatives |
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Direct Parent | Serotonins |
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Alternative Parents | |
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Substituents | - Serotonin
- 3-alkylindole
- Hydroxyindole
- Indole
- 2-arylethylamine
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 68.16%; H 6.86%; N 15.90%; O 9.08% | DFC |
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Melting Point | 167.5 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 20 mg/mL at 27 oC | HORN,AS (1981) |
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Experimental logP | 0.21 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa3 15 (20°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Serotonin, 5 TMS, GC-MS Spectrum | splash10-00di-1900000000-461c2a1f67418e6b5d6a | Spectrum | GC-MS | Serotonin, 5 TMS, GC-MS Spectrum | splash10-00di-1900000000-2286e87324e9f4a78cb4 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-927b865023cbba872101 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1910000000-02c17b4cd3336a8bf9b1 | Spectrum | GC-MS | Serotonin, 5 TMS, GC-MS Spectrum | splash10-00di-8900000000-4b838943ace80c8b7734 | Spectrum | GC-MS | Serotonin, 5 TMS, GC-MS Spectrum | splash10-00di-6900000000-a7dd5c569cf4d085d244 | Spectrum | GC-MS | Serotonin, 4 TMS, GC-MS Spectrum | splash10-00di-0900000000-2346e553f96cb980c8fc | Spectrum | GC-MS | Serotonin, 3 TMS, GC-MS Spectrum | splash10-00di-1900000000-01fbd5196188d4e0f21c | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-0002-9800000000-9ce9fb2286c3b7ea7719 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-461c2a1f67418e6b5d6a | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-2286e87324e9f4a78cb4 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-927b865023cbba872101 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1910000000-02c17b4cd3336a8bf9b1 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-4b838943ace80c8b7734 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-6900000000-a7dd5c569cf4d085d244 | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-0900000000-2346e553f96cb980c8fc | Spectrum | GC-MS | Serotonin, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-01fbd5196188d4e0f21c | Spectrum | Predicted GC-MS | Serotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001j-6900000000-95a89ff8a3b12e7e8e25 | Spectrum | Predicted GC-MS | Serotonin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-9450000000-52e0b628b7795c643362 | Spectrum | Predicted GC-MS | Serotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Serotonin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Serotonin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Serotonin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Serotonin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Serotonin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-1900000000-d64210214a1b3766ff6e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-004i-1900000000-66be80bf04de85d374b7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-662e21ddee556bb4a222 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-004i-0900000000-337ec7823cec887c8ad3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-8ac1f8742228b0c2ada5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00os-4900000000-fe28a76e9223ea9c3912 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-faf92490b8049363f990 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9500000000-c65e4440ede6c6f45d71 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0900000000-6acaf73bcd452e24b886 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0aor-0900000000-259227b20b82e6362059 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-02e9-5900000000-2f58fbed270523182158 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0002-9800000000-abcd0769bb17d07b3e38 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03di-0900000000-bf65d809200ea387ebf5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-03di-0900000000-8a171ac4fdc0474f7f48 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-03xr-0900000000-a0b7d8a671909c6f4ad1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-014i-1900000000-fa80d05236eabbafd678 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-4900000000-4e2e322d56fc9ee00edd | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-004i-0900000000-c79f0b03a8dc1da0a10a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-03fr-0900000000-9cb056cd56bae76589d0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0900000000-08840bc938c367dacbb2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03yi-0900000000-858936972fd87c0c0b14 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0159-4900000000-a8fc7dff385a4f51b88a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00p0-9400000000-7e4063d2b516ae59df84 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-bf65d809200ea387ebf5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-8a171ac4fdc0474f7f48 | 2017-09-14 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 5013 |
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ChEMBL ID | CHEMBL39 |
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KEGG Compound ID | C00780 |
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Pubchem Compound ID | 5202 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00259 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDV23-B:HDV23-B |
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EAFUS ID | Not Available |
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Dr. Duke ID | HIPPOPHAIN|HIPPOPHAINUM|5-HYDROXYTRYPTAMINE|SEROTONIN|SEROTIN |
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BIGG ID | 35982 |
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KNApSAcK ID | C00001429 |
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HET ID | SRO |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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abortifacient | 50691 | A chemical substance that interrupts pregnancy after implantation. | DUKE | allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti aggregant | | | DUKE | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti cholinesterase | 37733 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). | DUKE | anti convulsant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti depressant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antidote | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | anti endotoxic | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | anti gastric | | | DUKE | anti gastrisecretogogic | | | DUKE | anti mutilation | | | DUKE | anti Parkinsonian | 48407 | A drug used in the treatment of Parkinson's disease. | DUKE | anti predatory | | | DUKE | anti reserpine | | | DUKE | anti scoliotic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti Tourette's | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | bronchoconstrictor | 50141 | A drug which causes a narrowing of the lumen of a bronchus or bronchiole. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cardiovascular | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | cerebrophilic | | | DUKE | coagulant | | | DUKE | euphoriant | | | DUKE | hypertensive | | | DUKE | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | myorelaxant | | | DUKE | myostimulant | | | DUKE | neurotransmitter | 25512 | An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. | DUKE | oxytocic | 36063 | A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients). | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | secretogogue | | | DUKE | spasmogenic | | | DUKE | succinic-dehydrogenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | teratogenic | 50905 | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. | DUKE | ulcerogenic | | | DUKE | vasoactive | | | DUKE | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Aromatic-L-amino-acid decarboxylase | DDC | P20711 | Serotonin N-acetyltransferase | AANAT | Q16613 | 5-hydroxytryptamine receptor 7 | HTR7 | P34969 | 5-hydroxytryptamine receptor 1B | HTR1B | P28222 | 5-hydroxytryptamine receptor 1A | HTR1A | P08908 | 5-hydroxytryptamine receptor 3A | HTR3A | P46098 | 5-hydroxytryptamine receptor 1D | HTR1D | P28221 | 5-hydroxytryptamine receptor 4 | HTR4 | Q13639 | 5-hydroxytryptamine receptor 1F | HTR1F | P30939 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
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