Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2015-10-09 22:30:53 UTC
Primary IDFDB012158
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSerotonin
DescriptionIsol. from bananas and other fruits. Also from cotton (Gossypium hirsutum) [DFC]
CAS Number50-67-9
Structure
Thumb
Synonyms
SynonymSource
3-(2-Aminoethyl)-1H-indol-5-olChEBI
3-(2-Aminoethyl)-1H-indol-5-ol, 9CIdb_source
3-(2-Aminoethyl)-5-hydroxyindoledb_source
3-(2-Aminoethyl)indol-5-olHMDB
3-(b-Aminoethyl)-5-hydroxyindoleHMDB
5-HTChEBI
5-HTAHMDB
5-Hydroxy-3-(b-aminoethyl)indoleHMDB
5-Hydroxy-tryptamineHMDB
5-HydroxyltryptamineHMDB
5-HydroxytriptamineHMDB
5HTdb_source
AntemovisHMDB
Anthemovisterdb_source
DS substanceHMDB
EnteraminHMDB
Enteraminedb_source
Hippophainedb_source
Serotonindb_source
SerotonineChEBI
Thrombocytindb_source
Thrombotonindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.35 m3·mol-1ChemAxon
Polarizability19.31 Å3ChemAxon
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 KeyInChIKey=QZAYGJVTTNCVMB-UHFFFAOYSA-N
Isomeric SMILESNCCC1=CNC2=C1C=C(O)C=C2
Average Molecular Weight176.2151
Monoisotopic Molecular Weight176.094963016
Classification
DescriptionThis compound belongs to the class of organic compounds known as serotonins. These 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
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-1900000000-461c2a1f67418e6b5d6aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-1900000000-2286e87324e9f4a78cb4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1900000000-927b865023cbba872101View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1910000000-02c17b4cd3336a8bf9b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8900000000-4b838943ace80c8b7734View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-6900000000-a7dd5c569cf4d085d244View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0900000000-2346e553f96cb980c8fcView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1900000000-01fbd5196188d4e0f21cView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0002-9800000000-9ce9fb2286c3b7ea7719View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-461c2a1f67418e6b5d6aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-2286e87324e9f4a78cb4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-927b865023cbba872101View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1910000000-02c17b4cd3336a8bf9b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-8900000000-4b838943ace80c8b7734View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-6900000000-a7dd5c569cf4d085d244View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-0900000000-2346e553f96cb980c8fcView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-1900000000-01fbd5196188d4e0f21cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-6acaf73bcd452e24b886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-0900000000-259227b20b82e6362059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02e9-5900000000-2f58fbed270523182158View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0002-9800000000-abcd0769bb17d07b3e38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-bf65d809200ea387ebf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-1900000000-fa80d05236eabbafd678View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-4900000000-4e2e322d56fc9ee00eddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-c79f0b03a8dc1da0a10aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03fr-0900000000-9cb056cd56bae76589d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-d64210214a1b3766ff6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-08840bc938c367dacbb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03yi-0900000000-858936972fd87c0c0b14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-4900000000-a8fc7dff385a4f51b88aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00p0-9400000000-7e4063d2b516ae59df84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-bf65d809200ea387ebf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-8a171ac4fdc0474f7f48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-0900000000-a0b7d8a671909c6f4ad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
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.