Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:17 UTC
HMDB IDHMDB00259
Secondary Accession NumbersNone
Metabolite Identification
Common NameSerotonin
DescriptionSerotonin is a biochemical messenger and regulator, synthesized from the essential amino acid L-Tryptophan. 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. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns , including those responsible for feeding. 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 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. The three modes can affect a single neuronal circuit. (PMID: 16047543 ).
Structure
Thumb
Synonyms
  1. 3-(2-Aminoethyl)-1H-indol-5-ol
  2. 3-(2-Aminoethyl)indol-5-ol
  3. 3-(b-Aminoethyl)-5-hydroxyindole
  4. 5-HT
  5. 5-HTA
  6. 5-Hydroxy-3-(b-aminoethyl)indole
  7. 5-Hydroxy-tryptamine
  8. 5-Hydroxyltryptamine
  9. 5-Hydroxytriptamine
  10. 5-Hydroxytryptamine
  11. Antemovis
  12. DS substance
  13. Enteramin
  14. Enteramine
Chemical FormulaC10H12N2O
Average Molecular Weight176.2151
Monoisotopic Molecular Weight176.094963016
IUPAC Name3-(2-aminoethyl)-1H-indol-5-ol
Traditional IUPAC Nameserotonin
CAS Registry Number50-67-9
SMILES
NCCC1=CNC2=CC=C(O)C=C12
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIndoles
Sub ClassTryptamines and Derivatives
Other Descriptors
  • Biogenic amines(KEGG)
  • Indole alkaloids(KEGG)
  • Indoles
  • Tryptamines and Derivatives
  • primary amine(ChEBI)
  • tryptamines(ChEBI)
Substituents
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrole
Direct ParentSerotonins
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
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-1.9ALOGPS
pKa (strongest acidic)9.31ChemAxon
pKa (strongest basic)10ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count3ChemAxon
polar surface area62.04ChemAxon
rotatable bond count2ChemAxon
refractivity52.35ChemAxon
polarizability19.31ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • 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
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.07 (0-0.15) uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified0.70 +/- 0.32 uMChildren (1-13 year old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified0.74 +/- 0.28 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified0.97 +/- 0.28 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified0.0057-0.012 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0053-0.01 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.001 (0.0006-0.002) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.002-0.025 uMChildren (1-13 year old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.000002 uMAdult (>18 years old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0059 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified0.026 (0.017-0.040) umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified0.02 (0.004-0.0315) umol/mmol creatinineAdult (>18 years old)FemaleNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified0.065 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.03 (0.015-0.046) umol/mmol creatinineChildren (1-13 year old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified0.08 (0.04-0.12) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified<0.002 uMChildren (1-13 year old)Malesepiapterin reductase deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.0000036 uMAdult (>18 years old)Not SpecifiedHypothyroidism
Cerebrospinal Fluid (CSF)Detected and Quantified0.0044 (0.00-0.0093) uMAdult (>18 years old)BothParkinson's Disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.000004 uMAdult (>18 years old)BothHypothyroidism
Associated Disorders and Diseases
Disease References
Hypothyroidism
  • 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
Parkinson's disease
  • 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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012158
KNApSAcK IDC00001429
Chemspider ID5013
KEGG Compound IDC00780
BioCyc IDNot Available
BiGG ID35982
Wikipedia LinkSerotonin
NuGOwiki LinkHMDB00259
Metagene LinkHMDB00259
METLIN ID74
PubChem Compound5202
PDB IDSRO
ChEBI ID28790
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)Not Available
General References
  1. 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
  2. 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
  3. Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. Pubmed: 9931050
  4. King BM: The rise, fall, and resurrection of the ventromedial hypothalamus in the regulation of feeding behavior and body weight. Physiol Behav. 2006 Feb 28;87(2):221-44. Epub 2006 Jan 18. Pubmed: 16412483
  5. 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
  6. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. Blardi P, de Lalla A, Pieragalli D, De Franco V, Meini S, Ceccatelli L, Auteri A: Effect of iloprost on plasma asymmetric dimethylarginine and plasma and platelet serotonin in patients with peripheral arterial occlusive disease. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):175-82. Epub 2006 Jul 18. Pubmed: 16939882
  16. 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
  17. Ormazabal A, Vilaseca MA, Perez-Duenas B, Lambruschini N, Gomez L, Campistol J, Artuch R: Platelet serotonin concentrations in PKU patients under dietary control and tetrahydrobiopterin treatment. J Inherit Metab Dis. 2005;28(6):863-70. Pubmed: 16435178
  18. Ortiz J, Artigas F, Gelpi E: Serotonergic status in human blood. Life Sci. 1988;43(12):983-90. Pubmed: 2459577
  19. Sato T, Suzuki E, Yokoyama M, Semba J, Watanabe S, Miyaoka H: Chronic intraperitoneal injection of interferon-alpha reduces serotonin levels in various regions of rat brain, but does not change levels of serotonin transporter mRNA, nitrite or nitrate. Psychiatry Clin Neurosci. 2006 Aug;60(4):499-506. Pubmed: 16884454
  20. Konca K, Tiftik EN, Aslan G, Kanik A, Yalcin A: The effect of cromoglycate on time-dependent histamine and serotonin concentrations in stored blood products. Transfus Apher Sci. 2006 Apr;34(2):193-8. Epub 2006 Mar 3. Pubmed: 16516555
  21. De-Miguel FF, Trueta C: Synaptic and extrasynaptic secretion of serotonin. Cell Mol Neurobiol. 2005 Mar;25(2):297-312. Pubmed: 16047543

Enzymes

Gene Name:
AANAT
Uniprot ID:
Q16613
Reactions
Acetyl-CoA + Serotonin unknown Coenzyme A + N-Acetylserotonindetails
Gene Name:
MAOB
Uniprot ID:
P27338
Reactions
Serotonin + Water + Oxygen unknown 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
MAOA
Uniprot ID:
P21397
Reactions
Serotonin + Water + Oxygen unknown 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Gene Name:
DDC
Uniprot ID:
P20711
Reactions
Oxitriptan unknown Serotonin + CO(2)details
Oxitriptan unknown Serotonin + Carbon dioxidedetails
Gene Name:
AKR1C3
Uniprot ID:
P42330
Gene Name:
INMT
Uniprot ID:
O95050
Reactions
S-Adenosylmethionine + Serotonin unknown S-Adenosylhomocysteine + N-Methylserotonindetails
Gene Name:
IDO1
Uniprot ID:
P14902
Reactions
Serotonin + Oxygen unknown Formyl-5-hydroxykynurenaminedetails
Gene Name:
HTR4
Uniprot ID:
Q13639
Gene Name:
HTR7
Uniprot ID:
P34969
Gene Name:
SP1
Uniprot ID:
P08047
Gene Name:
HTR2B
Uniprot ID:
P41595
Gene Name:
HTR1B
Uniprot ID:
P28222
Gene Name:
HTR1F
Uniprot ID:
P30939
Gene Name:
HTR1A
Uniprot ID:
P08908
Gene Name:
HTR2A
Uniprot ID:
P28223
Gene Name:
HTR3A
Uniprot ID:
P46098
Gene Name:
HTR1D
Uniprot ID:
P28221
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Reactions
Serotonin + Oxygen unknown Formyl-5-hydroxykynurenaminedetails
Gene Name:
HTR3B
Uniprot ID:
O95264
Gene Name:
HTR1E
Uniprot ID:
P28566
Gene Name:
HTR5A
Uniprot ID:
P47898
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Reactions
Serotonin + 5-Methyltetrahydrofolic acid unknown 5-Methoxytryptamine + Tetrahydrofolic aciddetails
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Reactions
Serotonin + 5-Methyltetrahydrofolic acid unknown 5-Methoxytryptamine + Tetrahydrofolic aciddetails
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Reactions
Serotonin + 5-Methyltetrahydrofolic acid unknown 5-Methoxytryptamine + Tetrahydrofolic aciddetails
Gene Name:
WBSCR22
Uniprot ID:
O43709
Reactions
Serotonin + 5-Methyltetrahydrofolic acid unknown 5-Methoxytryptamine + Tetrahydrofolic aciddetails

Transporters

Gene Name:
SLC6A4
Uniprot ID:
P31645