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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-11-13 18:26:29 UTC
HMDB IDHMDB0000259
Secondary Accession Numbers
  • HMDB00259
Metabolite Identification
Common NameSerotonin
DescriptionSerotonin, 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. Within humans, serotonin participates in a number of enzymatic reactions. In particular, serotonin can be converted into serotonin through its interaction with the enzyme 5-hydroxytryptamine receptor 7. In addition, serotonin can be converted into serotonin through the action of the enzyme 5-hydroxytryptamine receptor 7. In humans, serotonin is involved in excitatory neural signalling through 5-htr 7 and serotonin. Outside of the human body, 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 swiss chards, nanking cherries, and dills. Serotonin has also been detected, but not quantified in, several different foods, such as fruits, bitter gourds, yellow wax beans, scarlet beans, and green bell peppers. This could make serotonin a potential biomarker for the consumption of these foods. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. Serotonin, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, brunner syndrome, hypothyroidism, and eosinophilic esophagitis; serotonin has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. Serotonin is also a microbial metabolite, urinary serotonin is produced by Candida, Streptococcus, Escherichia, and Enterococcus (PMID: 24621061 ). Not evaluated by the FDA, homeopathic product. For temporary relief of nervousness, anxiety, mood swings, joint pains, weakness, drowsiness, itching and lethargy. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state , sexual behavior, and others, and deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Such is the case of aggressive behavior and rhythmic motor patterns , including those responsible for feeding.
Structure
Data?1573669589
Synonyms
ValueSource
3-(2-Aminoethyl)-1H-indol-5-olChEBI
5-HTChEBI
5-HydroxytryptamineChEBI
EnteramineChEBI
SerotonineChEBI
ThrombocytinChEBI
ThrombotoninChEBI
HippophaineMeSH
HydroxytryptamineMeSH
5 HydroxytryptamineMeSH
3-(2-Aminoethyl)indol-5-olHMDB
3-(b-Aminoethyl)-5-hydroxyindoleHMDB
5-HTAHMDB
5-Hydroxy-3-(b-aminoethyl)indoleHMDB
5-Hydroxy-tryptamineHMDB
5-HydroxyltryptamineHMDB
5-HydroxytriptamineHMDB
AntemovisHMDB
DS SubstanceHMDB
EnteraminHMDB
Chemical FormulaC10H12N2O
Average Molecular Weight176.2151
Monoisotopic Molecular Weight176.094963016
IUPAC Name3-(2-aminoethyl)-1H-indol-5-ol
Traditional Nameserotonin
CAS Registry Number50-67-9
SMILES
NCCC1=CNC2=C1C=C(O)C=C2
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
InChI KeyQZAYGJVTTNCVMB-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility25.5 mg/mLHuman Metabolome Project
LogP0.21HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.5 g/LALOGPS
logP0.56ALOGPS
logP0.48ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area62.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.35 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-1900000000-461c2a1f67418e6b5d6aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-1900000000-2286e87324e9f4a78cb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-927b865023cbba872101JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1910000000-02c17b4cd3336a8bf9b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8900000000-4b838943ace80c8b7734JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-6900000000-a7dd5c569cf4d085d244JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0900000000-2346e553f96cb980c8fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1900000000-01fbd5196188d4e0f21cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9800000000-9ce9fb2286c3b7ea7719JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-461c2a1f67418e6b5d6aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-2286e87324e9f4a78cb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-927b865023cbba872101JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1910000000-02c17b4cd3336a8bf9b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8900000000-4b838943ace80c8b7734JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-6900000000-a7dd5c569cf4d085d244JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0900000000-2346e553f96cb980c8fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-01fbd5196188d4e0f21cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-6900000000-95a89ff8a3b12e7e8e25JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9450000000-52e0b628b7795c643362JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-6acaf73bcd452e24b886JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-0900000000-259227b20b82e6362059JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02e9-5900000000-2f58fbed270523182158JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0002-9800000000-abcd0769bb17d07b3e38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-bf65d809200ea387ebf5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-1900000000-fa80d05236eabbafd678JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-4900000000-4e2e322d56fc9ee00eddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-c79f0b03a8dc1da0a10aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03fr-0900000000-9cb056cd56bae76589d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-d64210214a1b3766ff6eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-08840bc938c367dacbb2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03yi-0900000000-858936972fd87c0c0b14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-4900000000-a8fc7dff385a4f51b88aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00p0-9400000000-7e4063d2b516ae59df84JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-bf65d809200ea387ebf5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900000000-a4e556450f24165aed15JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-657c360c251ec5745d1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qc-2900000000-397a6873ea727da9cc8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-253552852dde8abefca0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-5dd492dfc2d781e72254JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-1900000000-bed3bfffbc9cca506281JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Central Nervous System
  • Epidermis
  • Fibroblasts
  • Gut
  • Hypothalamus
  • Intestine
  • Kidney
  • Muscle
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.85 +/- 0.077 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.07 (0-0.15) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.70 +/- 0.32 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.74 +/- 0.28 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.97 +/- 0.28 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.30-2.00 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.41 +/- 0.33 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.14(0.72-1.72) uMChildren (1-13 uears old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0057-0.012 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0053-0.01 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.001 (0.0006-0.002) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002-0.025 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.000002 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0059 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.026 (0.017-0.040) umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.02 (0.004-0.0315) umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.1512 +/- 0.0566 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.892 +/- 3.264 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0110-0.0680 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.03 (0.015-0.046) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.08 (0.04-0.12) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0350-0.0670 umol/mmol creatinineChildren (1-13 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.61 +/- 0.096 uMAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified1.4(0.96-1.98) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction
details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.002 uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.0000036 uMAdult (>18 years old)Not SpecifiedHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0044 (0.00-0.0093) uMAdult (>18 years old)BothParkinson's Disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.000004 uMAdult (>18 years old)BothHypothyroidism details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.1758 +/- 0.057 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.1782 +/- 0.0798 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.755 +/- 3.583 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.124-0.233 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.188 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified0.221 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Parkinson's disease
  1. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Aromatic L-amino acid decarboxylase deficiency
  1. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
DrugBank IDDB08839
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012158
KNApSAcK IDC00001429
Chemspider ID5013
KEGG Compound IDC00780
BioCyc IDSEROTONIN
BiGG IDNot Available
Wikipedia LinkSerotonin
METLIN IDNot Available
PubChem Compound5202
PDB IDNot Available
ChEBI ID28790
Food Biomarker OntologyNot Available
VMH IDSRTN
References
Synthesis ReferenceHarley-Mason, John; Jackson, A. H. Hydroxytryptamines. I. Bufotenine, 6-hydroxybufotenine, and serotonin. Journal of the Chemical Society (1954), 1165-71.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Serebruany VL, Glassman AH, Malinin AI, Nemeroff CB, Musselman DL, van Zyl LT, Finkel MS, Krishnan KR, Gaffney M, Harrison W, Califf RM, O'Connor CM: Platelet/endothelial biomarkers in depressed patients treated with the selective serotonin reuptake inhibitor sertraline after acute coronary events: the Sertraline AntiDepressant Heart Attack Randomized Trial (SADHART) Platelet Substudy. Circulation. 2003 Aug 26;108(8):939-44. Epub 2003 Aug 11. [PubMed:12912814 ]
  2. Preuss HG, Garis RI, Bramble JD, Bagchi D, Bagchi M, Rao CV, Satyanarayana S: Efficacy of a novel calcium/potassium salt of (-)-hydroxycitric acid in weight control. Int J Clin Pharmacol Res. 2005;25(3):133-44. [PubMed:16366421 ]
  3. Lincoln J, Crowe R, Kamm MA, Burnstock G, Lennard-Jones JE: Serotonin and 5-hydroxyindoleacetic acid are increased in the sigmoid colon in severe idiopathic constipation. Gastroenterology. 1990 May;98(5 Pt 1):1219-25. [PubMed:1691117 ]
  4. Lundeberg L, Liang Y, Sundstrom E, Nordlind K, Verhofstad A, Liden S, Johansson O: Serotonin in human allergic contact dermatitis. An immunohistochemical and high-performance liquid chromatographic study. Arch Dermatol Res. 1999 May;291(5):269-74. [PubMed:10367709 ]
  5. Blardi P, Palazzuoli A, de Lalla A, Auteri A: Variations of peripheral markers of serotoninergic system in selected vascular patients. Nutr Metab Cardiovasc Dis. 2006 Apr;16(3):210-4. Epub 2005 Oct 21. [PubMed:16580588 ]
  6. Lommatzsch M, Hornych K, Zingler C, Schuff-Werner P, Hoppner J, Virchow JC: Maternal serum concentrations of BDNF and depression in the perinatal period. Psychoneuroendocrinology. 2006 Apr;31(3):388-94. Epub 2005 Nov 10. [PubMed:16289360 ]
  7. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  8. Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [PubMed:2580417 ]
  9. Lawrence KR, Adra M, Gillman PK: Serotonin toxicity associated with the use of linezolid: a review of postmarketing data. Clin Infect Dis. 2006 Jun 1;42(11):1578-83. Epub 2006 Apr 27. [PubMed:16652315 ]
  10. Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. [PubMed:16842443 ]
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  14. Eriksson O, Wall A, Marteinsdottir I, Agren H, Hartvig P, Blomqvist G, Langstrom B, Naessen T: Mood changes correlate to changes in brain serotonin precursor trapping in women with premenstrual dysphoria. Psychiatry Res. 2006 Mar 31;146(2):107-16. Epub 2006 Mar 2. [PubMed:16515859 ]
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Only showing the first 10 proteins. There are 27 proteins in total.

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:
AANAT
Uniprot ID:
Q16613
Molecular weight:
23343.8
Reactions
Acetyl-CoA + Serotonin → Coenzyme A + N-Acetylserotonindetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Reactions
5-Hydroxy-L-tryptophan → Serotonin + CO(2)details
5-Hydroxy-L-tryptophan → Serotonin + Carbon dioxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695
Reactions
S-Adenosylmethionine + Serotonin → S-Adenosylhomocysteine + N-Methylserotonindetails
General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
Serotonin + Oxygen → Formyl-5-hydroxykynurenaminedetails
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR4
Uniprot ID:
Q13639
Molecular weight:
43761.0
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165

Only showing the first 10 proteins. There are 27 proteins in total.