Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2018-05-28 23:34:24 UTC
Primary IDFDB012158
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 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 red bell peppers, swiss chards, and ryes. Serotonin has also been detected, but not quantified in, several different foods, such as carrots, eggplants, french plantains, common pea, and garden tomato (var.). This could make serotonin a potential biomarker for the consumption of these foods. Serotonin, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, hypothyroidism, and schizophrenia; serotonin has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency.
CAS Number50-67-9
Structure
Thumb
Synonyms
SynonymSource
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
3-(2-Aminoethyl)-1H-indol-5-ol, 9CIdb_source
3-(2-Aminoethyl)-5-hydroxyindoledb_source
5HTdb_source
Anthemovisterdb_source
DS substanceHMDB
Serotonindb_source
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 Area62.04 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
Chemical FormulaC10H12N2O
IUPAC name3-(2-aminoethyl)-1H-indol-5-ol
InChI IdentifierInChI=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
Isomeric SMILESNCCC1=CNC2=CC=C(O)C=C12
Average Molecular Weight176.2151
Monoisotopic Molecular Weight176.094963016
Classification
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:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 68.16%; H 6.86%; N 15.90%; O 9.08%DFC
Melting Point167.5 oC
Boiling PointNot Available
Experimental Water Solubility20 mg/mL at 27 oCHORN,AS (1981)
Experimental logP0.21HANSCH,C ET AL. (1995)
Experimental pKapKa3 15 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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-1900000000-461c2a1f67418e6b5d6aJSpectraViewer | 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
ChemSpider ID5013
ChEMBL IDCHEMBL39
KEGG Compound IDC00780
Pubchem Compound ID5202
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00259
CRC / DFC (Dictionary of Food Compounds) IDHDV23-B:HDV23-B
EAFUS IDNot Available
Dr. Duke IDHIPPOPHAIN|HIPPOPHAINUM|5-HYDROXYTRYPTAMINE|SEROTONIN|SEROTIN
BIGG ID35982
KNApSAcK IDC00001429
HET IDSRO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti aggregantDUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti endotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti gastricDUKE
anti gastrisecretogogicDUKE
anti mutilationDUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti predatoryDUKE
anti reserpineDUKE
anti scoliotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Tourette's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bronchoconstrictor50141 A drug which causes a narrowing of the lumen of a bronchus or bronchiole.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cerebrophilicDUKE
coagulantDUKE
euphoriantDUKE
hypertensiveDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
myorelaxantDUKE
myostimulantDUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.DUKE
oxytocic36063 A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
secretogogueDUKE
spasmogenicDUKE
succinic-dehydrogenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
ulcerogenicDUKE
vasoactiveDUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Serotonin N-acetyltransferaseAANATQ16613
5-hydroxytryptamine receptor 7HTR7P34969
5-hydroxytryptamine receptor 1BHTR1BP28222
5-hydroxytryptamine receptor 1AHTR1AP08908
5-hydroxytryptamine receptor 3AHTR3AP46098
5-hydroxytryptamine receptor 1DHTR1DP28221
5-hydroxytryptamine receptor 4HTR4Q13639
5-hydroxytryptamine receptor 1FHTR1FP30939
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).