| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:27:33 UTC |
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| Update Date | 2020-06-04 19:52:39 UTC |
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| BMDB ID | BMDB0000259 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common 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, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, eosinophilic esophagitis, and brunner syndrome; serotonin has also been linked to several inborn metabolic disorders including sepiapterin reductase deficiency and aromatic l-amino acid decarboxylase deficiency. |
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| Structure | |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C10H12N2O |
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| Average Molecular Weight | 176.2151 |
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| Monoisotopic Molecular Weight | 176.094963016 |
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| IUPAC Name | 3-(2-aminoethyl)-1H-indol-5-ol |
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| Traditional Name | serotonin |
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| CAS Registry Number | 50-67-9 |
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| SMILES | NCCC1=CNC2=C1C=C(O)C=C2 |
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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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| Chemical Taxonomy |
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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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 25.5 mg/mL | Human Metabolome Project | | LogP | 0.21 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Adrenal Medulla
- Bladder
- Blood
- Brain
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Skeletal Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Medulla | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 9 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 4-13 uM | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 2 +/- 1 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.1 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.02 +/- 0.04 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.02 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000259 |
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| DrugBank ID | DB08839 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012158 |
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| KNApSAcK ID | C00001429 |
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| Chemspider ID | 5013 |
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| KEGG Compound ID | C00780 |
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| BioCyc ID | SEROTONIN |
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| BiGG ID | Not Available |
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| Wikipedia Link | Serotonin |
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| METLIN ID | Not Available |
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| PubChem Compound | 5202 |
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| PDB ID | Not Available |
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| ChEBI ID | 28790 |
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| References |
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| Synthesis Reference | Harley-Mason, John; Jackson, A. H. Hydroxytryptamines. I. Bufotenine, 6-hydroxybufotenine, and serotonin. Journal of the Chemical Society (1954), 1165-71. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | Not Available |
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