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Serotonin (FDB012158)

Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:17 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 green beans, red bell peppers, and swiss chards. Serotonin has also been detected, but not quantified in, several different foods, such as grapes, cocoa beans, pepper (c. frutescens), avocado, and common pea. 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, schizophrenia, parkinson's disease, and hypothyroidism; serotonin has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency.
CAS Number50-67-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSerotonin, 5 TMS, GC-MS Spectrumsplash10-00di-1900000000-461c2a1f67418e6b5d6aSpectrum
GC-MSSerotonin, 5 TMS, GC-MS Spectrumsplash10-00di-1900000000-2286e87324e9f4a78cb4Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-927b865023cbba872101Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1910000000-02c17b4cd3336a8bf9b1Spectrum
GC-MSSerotonin, 5 TMS, GC-MS Spectrumsplash10-00di-8900000000-4b838943ace80c8b7734Spectrum
GC-MSSerotonin, 5 TMS, GC-MS Spectrumsplash10-00di-6900000000-a7dd5c569cf4d085d244Spectrum
GC-MSSerotonin, 4 TMS, GC-MS Spectrumsplash10-00di-0900000000-2346e553f96cb980c8fcSpectrum
GC-MSSerotonin, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-01fbd5196188d4e0f21cSpectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-0002-9800000000-9ce9fb2286c3b7ea7719Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-461c2a1f67418e6b5d6aSpectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-2286e87324e9f4a78cb4Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-927b865023cbba872101Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1910000000-02c17b4cd3336a8bf9b1Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-4b838943ace80c8b7734Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-6900000000-a7dd5c569cf4d085d244Spectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-0900000000-2346e553f96cb980c8fcSpectrum
GC-MSSerotonin, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-01fbd5196188d4e0f21cSpectrum
Predicted GC-MSSerotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-6900000000-95a89ff8a3b12e7e8e25Spectrum
Predicted GC-MSSerotonin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9450000000-52e0b628b7795c643362Spectrum
Predicted GC-MSSerotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSerotonin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSerotonin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSerotonin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSerotonin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSerotonin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-d64210214a1b3766ff6e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-66be80bf04de85d374b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-662e21ddee556bb4a2222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0900000000-337ec7823cec887c8ad32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8ac1f8742228b0c2ada52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00os-4900000000-fe28a76e9223ea9c39122021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-faf92490b8049363f9902021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-c65e4440ede6c6f45d712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-6acaf73bcd452e24b8862012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-0900000000-259227b20b82e63620592012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02e9-5900000000-2f58fbed2705231821582012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0002-9800000000-abcd0769bb17d07b3e382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-bf65d809200ea387ebf52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-8a171ac4fdc0474f7f482012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-1900000000-fa80d05236eabbafd6782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-4900000000-4e2e322d56fc9ee00edd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-c79f0b03a8dc1da0a10a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03fr-0900000000-9cb056cd56bae76589d02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-08840bc938c367dacbb22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03yi-0900000000-858936972fd87c0c0b142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-4900000000-a8fc7dff385a4f51b88a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00p0-9400000000-7e4063d2b516ae59df842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-bf65d809200ea387ebf52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-8a171ac4fdc0474f7f482017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).