Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Serotonin (HMDB00259)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-13 17:03:53 -0600
HMDB ID HMDB00259
Secondary Accession Numbers None
Metabolite Identification
Common Name Serotonin
Description Serotonin 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H12N2O
Average Molecular Weight 176.2151
Monoisotopic Molecular Weight 176.094963016
IUPAC Name 3-(2-aminoethyl)-1H-indol-5-ol
Traditional IUPAC Name serotonin
CAS Registry Number 50-67-9
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 Key QZAYGJVTTNCVMB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Tryptamines 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 Parent Serotonins
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
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)
Predicted Properties
Property Value Source
Water Solubility 2.5 g/L ALOGPS
LogP 0.56 ALOGPS
LogP 0.48 ChemAxon
LogS -1.85 ALOGPS
pKa (strongest acidic) 9.31 ChemAxon
pKa (strongest basic) 10 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 62.04 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 52.35 ChemAxon
Polarizability 19.31 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Epidermis
  • Brain
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Gut
  • Central Nervous System
  • Hypothalamus
  • Skeletal
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.07 (0-0.15) uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.70 +/- 0.32 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.74 +/- 0.28 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
0.97 +/- 0.28 uM Adult (>18 years old) Female Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0057-0.012 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0053-0.01 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.001 (0.0006-0.002) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.002-0.025 uM Children (1-13 year old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00001 +/- 0.000002 uM Adult (>18 years old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0059 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.026 (0.017-0.040) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
0.02 (0.004-0.0315) umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
0.065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.03 (0.015-0.046) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.08 (0.04-0.12) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
<0.002 uM Children (1-13 year old) Male sepiapterin reductase deficiency Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00001 +/- 0.0000036 uM Adult (>18 years old) Not Specified Hypothyroidism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0044 (0.00-0.0093) uM Adult (>18 years old) Both Parkinson's Disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00001 +/- 0.000004 uM Adult (>18 years old) Both Hypothyroidism Not Available
Associated Disorders and Diseases
Disease References
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 Link_out
    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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012158
      KNApSAcK ID C00001429 Link_out
      Chemspider ID 5013 Link_out
      KEGG Compound ID C00780 Link_out
      BioCyc ID Not Available
      BiGG ID 35982 Link_out
      Wikipedia Link Serotonin Link_out
      NuGOwiki Link HMDB00259 Link_out
      Metagene Link HMDB00259 Link_out
      METLIN ID 74 Link_out
      PubChem Compound 5202 Link_out
      PDB ID SRO Link_out
      ChEBI ID 28790 Link_out
      References
      Synthesis Reference Harley-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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      13. 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 Link_out
      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 Link_out
      15. 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 Link_out
      16. Ortiz J, Artigas F, Gelpi E: Serotonergic status in human blood. Life Sci. 1988;43(12):983-90. Pubmed: 2459577 Link_out
      17. 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 Link_out
      18. 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 Link_out
      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 Link_out
      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 Link_out
      Enzymes
      Name: Serotonin N-acetyltransferase
      Reactions:
      • acetyl-CoA + a 2-arylethylamine = CoA + an N-acetyl-2-arylethylamine [RN:R03760]
      Gene Name: AANAT
      Uniprot ID: Q16613 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amine oxidase [flavin-containing] B
      Reactions:
      • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
      Gene Name: MAOB
      Uniprot ID: P27338 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amine oxidase [flavin-containing] A
      Reactions:
      • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
      Gene Name: MAOA
      Uniprot ID: P21397 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aromatic-L-amino-acid decarboxylase
      Reactions:
      • (1) 3,4-dihydroxy-L-phenylalanine = dopamine + CO2 [RN:R02080]
      • (2) 5-hydroxy-L-tryptophan = 5-hydroxytryptamine + CO2 [RN:R02701]
      Gene Name: DDC
      Uniprot ID: P20711 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aldo-keto reductase family 1 member C3
      Reactions:
      • trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+ [RN:R00814]
      Gene Name: AKR1C3
      Uniprot ID: P42330 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Indolethylamine N-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + an amine = S-adenosyl-L-homocysteine + a methylated amine [RN:R02808]
      Gene Name: INMT
      Uniprot ID: O95050 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Indoleamine 2,3-dioxygenase 1
      Reactions:
      • (1) D-tryptophan + O2 = N-formyl-D-kynurenine [RN:R07362]
      • (2) L-tryptophan + O2 = N-formyl-L-kynurenine [RN:R00678]
      Gene Name: IDO1
      Uniprot ID: P14902 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Protein arginine N-methyltransferase 3
      Reactions:
        Gene Name: PRMT3
        Uniprot ID: O60678 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 5-hydroxytryptamine receptor 4
        Reactions:
          Gene Name: HTR4
          Uniprot ID: Q13639 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 5-hydroxytryptamine receptor 7
          Reactions:
            Gene Name: HTR7
            Uniprot ID: P34969 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Transcription factor Sp1
            Reactions:
              Gene Name: SP1
              Uniprot ID: P08047 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: 5-hydroxytryptamine receptor 2B
              Reactions:
                Gene Name: HTR2B
                Uniprot ID: P41595 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: 5-hydroxytryptamine receptor 1B
                Reactions:
                  Gene Name: HTR1B
                  Uniprot ID: P28222 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: 5-hydroxytryptamine receptor 1F
                  Reactions:
                    Gene Name: HTR1F
                    Uniprot ID: P30939 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: 5-hydroxytryptamine receptor 1A
                    Reactions:
                      Gene Name: HTR1A
                      Uniprot ID: P08908 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: 5-hydroxytryptamine receptor 2A
                      Reactions:
                        Gene Name: HTR2A
                        Uniprot ID: P28223 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: 5-hydroxytryptamine receptor 3A
                        Reactions:
                          Gene Name: HTR3A
                          Uniprot ID: P46098 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: 5-hydroxytryptamine receptor 1D
                          Reactions:
                            Gene Name: HTR1D
                            Uniprot ID: P28221 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Indoleamine 2,3-dioxygenase 2
                            Reactions:
                              Gene Name: IDO2
                              Uniprot ID: Q6ZQW0 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: 5-hydroxytryptamine receptor 3B
                              Reactions:
                                Gene Name: HTR3B
                                Uniprot ID: O95264 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: 5-hydroxytryptamine receptor 1E
                                Reactions:
                                  Gene Name: HTR1E
                                  Uniprot ID: P28566 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: 5-hydroxytryptamine receptor 5A
                                  Reactions:
                                    Gene Name: HTR5A
                                    Uniprot ID: P47898 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA
                                    Transporters
                                    Name: Sodium-dependent serotonin transporter
                                    Reactions:
                                    • --- []
                                    Gene Name: SLC6A4
                                    Uniprot ID: P31645 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA