serotonin (CHEBI:28790)

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CHEBI:28790 - serotonin

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ChEBI Name	serotonin

ChEBI ID	CHEBI:28790

Definition	A primary amino compound that is the 5-hydroxy derivative of tryptamine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:49894, CHEBI:1420, CHEBI:26652

Supplier Information	ChemicalBook:CB8742186, ChemicalBook:CB64796923, eMolecules:514488, ZINC000003645145

Download	Molfile XML SDF

more structures >>

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Mrv0541 02171416153D

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Mrv0541 02171416153D

25 26 0 0 0 0 999 V2000

-2.7470 2.4070 -0.0690 O 0 0 0 0 0 0 0 0 0 0 0 0

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1.1560 -0.6980 -0.3640 C 0 0 0 0 0 0 0 0 0 0 0 0

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2.3690 0.1350 -0.6870 C 0 0 1 0 0 0 0 0 0 0 0 0

2.9580 0.7020 0.6060 C 0 0 1 0 0 0 0 0 0 0 0 0

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3.9140 2.2430 -0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5490 1.9000 1.1280 H 0 0 0 0 0 0 0 0 0 0 0 0

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M END): 20 ms

reading 25 atoms

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Wikipedia	License
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and peripheral tissues. It is involved in mood, cognition, reward, learning, memory, and physiological processes such as vomiting and vasoconstriction. In the CNS, serotonin regulates mood, appetite, and sleep. Most of the body's serotonin—about 90%—is synthesized in the gastrointestinal tract by enterochromaffin cells, where it regulates intestinal movements. It is also produced in smaller amounts in the brainstem's raphe nuclei, the skin's Merkel cells, pulmonary neuroendocrine cells, and taste receptor cells of the tongue. Once secreted, serotonin is taken up by platelets in the blood, which release it during clotting to promote vasoconstriction and platelet aggregation. Around 8% of the body's serotonin is stored in platelets, and 1–2% is found in the CNS. Serotonin acts as both a vasoconstrictor and vasodilator depending on concentration and context, influencing hemostasis and blood pressure regulation. It plays a role in stimulating myenteric neurons and enhancing gastrointestinal motility through uptake and release cycles in platelets and surrounding tissue. Biochemically, serotonin is an indoleamine synthesized from tryptophan and metabolized primarily in the liver to 5-hydroxyindoleacetic acid (5-HIAA). Serotonin is targeted by several classes of antidepressants, including selective serotonin reuptake inhibitors (SSRIs) and serotonin–norepinephrine reuptake inhibitors (SNRIs), which block reabsorption in the synapse to elevate its levels. It is found in nearly all bilateral animals, including insects and worms, and also occurs in fungi and plants. In plants and insect venom, it serves a defensive function by inducing pain. Serotonin released by pathogenic amoebae may cause diarrhea in the human gut, while its presence in seeds and fruits is thought to stimulate digestion and facilitate seed dispersal.
Read full article at Wikipedia

Formula

C10H12N2O

Net Charge

Average Mass

176.215

Monoisotopic Mass

176.09496

InChI

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

InChIKey

QZAYGJVTTNCVMB-UHFFFAOYSA-N

SMILES

C1=CC(=CC=2C(=CNC12)CCN)O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Paramuricea clavata (NCBI:txid317549)	CH2Cl2:MeOH(1:1) extract of lyophilized material See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. molecular messenger (via monoamine molecular messenger )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	serotonin (CHEBI:28790) has functional parent tryptamine (CHEBI:16765) serotonin (CHEBI:28790) has role human metabolite (CHEBI:77746) serotonin (CHEBI:28790) has role mouse metabolite (CHEBI:75771) serotonin (CHEBI:28790) has role neurotransmitter (CHEBI:25512) serotonin (CHEBI:28790) is a hydroxyindoles (CHEBI:84729) serotonin (CHEBI:28790) is a monoamine molecular messenger (CHEBI:25375) serotonin (CHEBI:28790) is a phenols (CHEBI:33853) serotonin (CHEBI:28790) is a primary amino compound (CHEBI:50994) serotonin (CHEBI:28790) is a tryptamines (CHEBI:27162) serotonin (CHEBI:28790) is conjugate base of serotonin(1+) (CHEBI:350546)

Incoming	(2E)-N-{2-[5,5'-dihydroxy-3'-(2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}ethyl)-1H,1'H-[4,4'-biindole]-3-yl]ethyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid (CHEBI:184799) has functional parent serotonin (CHEBI:28790) (2E)-N-{2-[5,5'-dihydroxy-3'-(2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}ethyl)-1H,1'H-[4,4'-biindole]-3-yl]ethyl}-3-(4-hydroxyphenyl)prop-2-enimidic acid (CHEBI:185584) has functional parent serotonin (CHEBI:28790) 1-(5-methoxy-1H-indol-3-yl)-2-propanamine (CHEBI:125422) has functional parent serotonin (CHEBI:28790) 1-[5-(thiophen-2-ylmethoxy)-1H-indol-3-yl]-2-propanamine (CHEBI:91556) has functional parent serotonin (CHEBI:28790) 2,2,2-trideuterio-N-[1,1,2,2-tetradeuterio-2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide (CHEBI:125590) has functional parent serotonin (CHEBI:28790) 2-methylserotonin (CHEBI:31085) has functional parent serotonin (CHEBI:28790) 3-(2-aminoethyl)-6-methoxy-1H-indol-5-ol 2-amino-3-methyl-4H-imidazol-5-one (CHEBI:125692) has functional parent serotonin (CHEBI:28790) 3-(2-aminoethyl)-7-methoxy-1H-indol-5-ol 2-amino-3-methyl-4H-imidazol-5-one (CHEBI:125691) has functional parent serotonin (CHEBI:28790) 5-Methoxy DL-tryptophan (CHEBI:86571) has functional parent serotonin (CHEBI:28790) 5-Methoxy-DL-tryptophan (CHEBI:194846) has functional parent serotonin (CHEBI:28790) 5-methoxytryptamine (CHEBI:2089) has functional parent serotonin (CHEBI:28790) 5-nonyloxytryptamine (CHEBI:64149) has functional parent serotonin (CHEBI:28790) N,O-dimethylserotonin (CHEBI:189635) has functional parent serotonin (CHEBI:28790) N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-L-glutamine residue (CHEBI:167174) has functional parent serotonin (CHEBI:28790) N-acylserotonin (CHEBI:134175) has functional parent serotonin (CHEBI:28790) N-arachidonoyl-2-oxoserotonin (CHEBI:132256) has functional parent serotonin (CHEBI:28790) N-methylserotonin (CHEBI:48294) has functional parent serotonin (CHEBI:28790) Creatinine sulfate mixture with serotonin (CHEBI:166585) has functional parent serotonin (CHEBI:28790) N6-cis-p-Coumaroylserotonin (CHEBI:175113) has functional parent serotonin (CHEBI:28790) Serotonin hydrochloride (CHEBI:181195) has functional parent serotonin (CHEBI:28790) serotonin(1+) (CHEBI:350546) is conjugate acid of serotonin (CHEBI:28790)

IUPAC Name

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

Synonyms	Sources
3-(2-Aminoethyl)-1H-indol-5-ol	KEGG COMPOUND
3-(2-Aminoethyl)-1H-indol-5-ol	KEGG COMPOUND
5-HT	IUPHAR
5-Hydroxytryptamine	KEGG COMPOUND
Enteramine	KEGG COMPOUND
Serotonin	KEGG COMPOUND
SEROTONIN	PDBeChem
sérotonine	ChEBI
thrombocytin	ChemIDplus
thrombotonin	ChemIDplus

Manual Xrefs	Databases
C00001429	KNApSAcK
C00780	KEGG COMPOUND
HMDB0000259	HMDB
LSM-6589	LINCS
Serotonin	Wikipedia
SEROTONIN	MetaCyc
SRO	PDBeChem
View more database links

Registry Numbers	Types	Sources
143524	Reaxys Registry Number	Reaxys
1861995	Gmelin Registry Number	Gmelin
50-67-9	CAS Registry Number	KEGG COMPOUND
50-67-9	CAS Registry Number	ChemIDplus

Citations

Marshall AM, Hernandez LL, Horseman ND (2014)
Serotonin and serotonin transport in the regulation of lactation.
Journal of mammary gland biology and neoplasia 19, 139-146 [PubMed:24136337]
[show Abstract]

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Nocito A, Dahm F, Jochum W, Jang JH, Georgiev P, Bader M, Graf R, Clavien PA (2008)
Serotonin regulates macrophage-mediated angiogenesis in a mouse model of colon cancer allografts.
Cancer research 68, 5152-5158 [PubMed:18593914]
[show Abstract]

Last Modified

14 December 2016

CHEBI:28790 - serotonin

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