AFCDB: Serotonin (FDB012158)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:01 UTC

Update date

2019-11-26 03:06:17 UTC

Primary ID

FDB012158

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Serotonin

Description

Serotonin, 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 Number

50-67-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	2.5 g/L	ALOGPS
logP	0.56	ALOGPS
logP	0.48	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	62.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.35 m³·mol⁻¹	ChemAxon
Polarizability	19.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12N2O

IUPAC name

3-(2-aminoethyl)-1H-indol-5-ol

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

Isomeric SMILES

NCCC1=CNC2=CC=C(O)C=C12

Average Molecular Weight

176.2151

Monoisotopic Molecular Weight

176.094963016

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:28790 )
monoamine molecular messenger (CHEBI:28790 )
primary amino compound (CHEBI:28790 )
tryptamines (CHEBI:28790 )
Biogenic amines (C00780 )
Indole alkaloids (C00780 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Endocrine disorders:

Hypothyroidism

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Fungi:

Candida

Plant:

Microbe:

Escherichia:

Escherichia coli

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	0.21	HANSCH,C ET AL. (1995)
Experimental pKa	pKa3 15 (20°)	DFC
Experimental Water Solubility	20 mg/mL at 27 oC	HORN,AS (1981)
Isoelectric point	Not Available
Mass Composition	C 68.16%; H 6.86%; N 15.90%; O 9.08%	DFC
Melting Point	167.5 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Serotonin, 5 TMS, GC-MS Spectrum	splash10-00di-1900000000-461c2a1f67418e6b5d6a	Spectrum
GC-MS	Serotonin, 5 TMS, GC-MS Spectrum	splash10-00di-1900000000-2286e87324e9f4a78cb4	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-927b865023cbba872101	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	Spectrum
GC-MS	Serotonin, 5 TMS, GC-MS Spectrum	splash10-00di-8900000000-4b838943ace80c8b7734	Spectrum
GC-MS	Serotonin, 5 TMS, GC-MS Spectrum	splash10-00di-6900000000-a7dd5c569cf4d085d244	Spectrum
GC-MS	Serotonin, 4 TMS, GC-MS Spectrum	splash10-00di-0900000000-2346e553f96cb980c8fc	Spectrum
GC-MS	Serotonin, 3 TMS, GC-MS Spectrum	splash10-00di-1900000000-01fbd5196188d4e0f21c	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-0002-9800000000-9ce9fb2286c3b7ea7719	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-461c2a1f67418e6b5d6a	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-2286e87324e9f4a78cb4	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-927b865023cbba872101	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-4b838943ace80c8b7734	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-6900000000-a7dd5c569cf4d085d244	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-0900000000-2346e553f96cb980c8fc	Spectrum
GC-MS	Serotonin, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-01fbd5196188d4e0f21c	Spectrum
Predicted GC-MS	Serotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001j-6900000000-95a89ff8a3b12e7e8e25	Spectrum
Predicted GC-MS	Serotonin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9450000000-52e0b628b7795c643362	Spectrum
Predicted GC-MS	Serotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Serotonin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Serotonin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Serotonin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Serotonin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Serotonin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-1900000000-d64210214a1b3766ff6e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-66be80bf04de85d374b7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-662e21ddee556bb4a222	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-337ec7823cec887c8ad3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8ac1f8742228b0c2ada5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00os-4900000000-fe28a76e9223ea9c3912	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-faf92490b8049363f990	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-c65e4440ede6c6f45d71	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-6acaf73bcd452e24b886	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-0900000000-259227b20b82e6362059	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02e9-5900000000-2f58fbed270523182158	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0002-9800000000-abcd0769bb17d07b3e38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-0900000000-bf65d809200ea387ebf5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03xr-0900000000-a0b7d8a671909c6f4ad1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-1900000000-fa80d05236eabbafd678	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-4900000000-4e2e322d56fc9ee00edd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-c79f0b03a8dc1da0a10a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-03fr-0900000000-9cb056cd56bae76589d0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-08840bc938c367dacbb2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03yi-0900000000-858936972fd87c0c0b14	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0159-4900000000-a8fc7dff385a4f51b88a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00p0-9400000000-7e4063d2b516ae59df84	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-bf65d809200ea387ebf5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00259

CRC / DFC (Dictionary of Food Compounds) ID

HDV23-B:HDV23-B

EAFUS ID

Not Available

Dr. Duke ID

HIPPOPHAIN|HIPPOPHAINUM|5-HYDROXYTRYPTAMINE|SEROTONIN|SEROTIN

BIGG ID

35982

KNApSAcK ID

C00001429

HET ID

SRO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	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 aggregant			DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti endotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti gastric			DUKE

Showing 1 to 10 of 38 entries

Enzymes

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Name	Gene Name	UniProt ID
5-hydroxytryptamine receptor 1A	HTR1A	P08908
5-hydroxytryptamine receptor 1B	HTR1B	P28222
5-hydroxytryptamine receptor 1D	HTR1D	P28221
5-hydroxytryptamine receptor 1F	HTR1F	P30939
5-hydroxytryptamine receptor 3A	HTR3A	P46098
5-hydroxytryptamine receptor 4	HTR4	Q13639
5-hydroxytryptamine receptor 7	HTR7	P34969
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Serotonin N-acetyltransferase	AANAT	Q16613

Showing 1 to 9 of 9 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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).

Serotonin (FDB012158)

Structure for FDB012158 (Serotonin)