You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:42:48 UTC
Update Date2021-04-30 20:57:45 UTC
LmdbLMDB00120
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
ValueSource
3-(2-Aminoethyl)-1H-indol-5-olChEBI
5-HTChEBI
5-HydroxytryptamineChEBI
EnteramineChEBI
SerotonineChEBI
ThrombocytinChEBI
ThrombotoninChEBI
HippophaineHMDB
HydroxytryptamineHMDB
5 HydroxytryptamineHMDB
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=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
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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 Area62.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.35 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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-1900000000-461c2a1f67418e6b5d6aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-1900000000-2286e87324e9f4a78cb4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-927b865023cbba872101Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1910000000-02c17b4cd3336a8bf9b1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8900000000-4b838943ace80c8b7734Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-6900000000-a7dd5c569cf4d085d244Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0900000000-2346e553f96cb980c8fcSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1900000000-01fbd5196188d4e0f21cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9800000000-9ce9fb2286c3b7ea7719Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-461c2a1f67418e6b5d6aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-2286e87324e9f4a78cb4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-927b865023cbba872101Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1910000000-02c17b4cd3336a8bf9b1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8900000000-4b838943ace80c8b7734Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-6900000000-a7dd5c569cf4d085d244Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0900000000-2346e553f96cb980c8fcSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1900000000-01fbd5196188d4e0f21cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-6900000000-95a89ff8a3b12e7e8e25Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9450000000-52e0b628b7795c643362Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-6acaf73bcd452e24b886Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-0900000000-259227b20b82e6362059Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02e9-5900000000-2f58fbed270523182158Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0002-9800000000-abcd0769bb17d07b3e38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-bf65d809200ea387ebf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-1900000000-fa80d05236eabbafd678Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-4900000000-4e2e322d56fc9ee00eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-c79f0b03a8dc1da0a10aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03fr-0900000000-9cb056cd56bae76589d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-d64210214a1b3766ff6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-08840bc938c367dacbb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03yi-0900000000-858936972fd87c0c0b14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-4900000000-a8fc7dff385a4f51b88aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00p0-9400000000-7e4063d2b516ae59df84Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-bf65d809200ea387ebf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900000000-a4e556450f24165aed15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-657c360c251ec5745d1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qc-2900000000-397a6873ea727da9cc8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-253552852dde8abefca0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-5dd492dfc2d781e72254Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-1900000000-bed3bfffbc9cca506281Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified1.02 +/- 0.04 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified4.0838 +/- 3.2922 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.18 +/- 3.6443 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.9 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified2.4 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified2.7 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified3.9 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified4.0627 +/- 2.7803 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.4143 +/- 3.835 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.2054 +/- 2.3335 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified11.38 +/- 5.62 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified6.4916 +/- 2.9845 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.5533 +/- 3.2329 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.2803 +/- 3.5856 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.5804 +/- 3.286 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.6349 +/- 3.2179 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.4123 +/- 3.4583 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.8027 +/- 2.9648 uM
Normal
Ovine
    • Goldansaz et al.,...
details
DrugBank IDDB08839
HMDB IDHMDB0000259
FooDB IDFDB012158
Phenol Explorer IDNot Available
KNApSAcK IDC00001429
BiGG IDNot Available
BioCyc IDSEROTONIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSerotonin
Chemspider ID5013
ChEBI ID28790
PubChem Compound ID5202
Kegg Compound IDC00780
YMDB IDNot Available
ECMDB IDM2MDB004612
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. De-Miguel FF, Trueta C: Synaptic and extrasynaptic secretion of serotonin. Cell Mol Neurobiol. 2005 Mar;25(2):297-312. [16047543 ]