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:CB6119335, eMolecules:969219, ZINC000000057058

Download	Molfile XML SDF

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Mrv0541 02171416153D

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Mrv0541 02171416153D

25 26 0 0 0 0 999 V2000

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M END): 16 ms

reading 25 atoms

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Wikipedia	License
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex, touching on diverse functions including mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vasoconstriction. Serotonin is produced in the central nervous system (CNS), specifically in the brainstem's raphe nuclei, the skin's Merkel cells, pulmonary neuroendocrine cells and the tongue's taste receptor cells. Approximately 90% of the serotonin the human body produces is in the gastrointestinal tract's enterochromaffin cells, where it regulates intestinal movements. Additionally, it is stored in blood platelets and is released during agitation and vasoconstriction, where it then acts as an agonist to other platelets. About 8% is found in platelets and 1–2% in the CNS. The serotonin is secreted luminally and basolaterally, which leads to increased serotonin uptake by circulating platelets and activation after stimulation, which gives increased stimulation of myenteric neurons and gastrointestinal motility. The remainder is synthesized in serotonergic neurons of the CNS, where it has various functions, including the regulation of mood, appetite, and sleep. Serotonin secreted from the enterochromaffin cells eventually finds its way out of tissues into the blood. There, it is actively taken up by blood platelets, which store it. When the platelets bind to a clot, they release serotonin, which can serve as a vasoconstrictor or a vasodilator while regulating hemostasis and blood clotting. In high concentrations, serotonin acts as a vasoconstrictor by contracting endothelial smooth muscle directly or by potentiating the effects of other vasoconstrictors (e.g. angiotensin II and norepinephrine). The vasoconstrictive property is mostly seen in pathologic states affecting the endothelium – such as atherosclerosis or chronic hypertension. In normal physiologic states, vasodilation occurs through the serotonin-mediated release of nitric oxide (NO) from endothelial cells and the inhibition of the release of norepinephrine from adrenergic nerves. Serotonin is also a growth factor for some types of cells, which may give it a role in wound healing. There are various serotonin receptors. Biochemically, the indoleamine molecule derives from the amino acid tryptophan. Serotonin is metabolized mainly to 5-hydroxyindoleacetic acid (5-HIAA), chiefly by the liver. Several classes of antidepressants, such as selective serotonin reuptake inhibitors (SSRIs) and serotonin–norepinephrine reuptake inhibitors (SNRIs), interfere with the normal reabsorption of serotonin after it is done with the transmission of the signal, therefore augmenting the neurotransmitter levels in the synapses. Besides mammals, serotonin is found in all bilateral animals including worms and insects, as well as in fungi and in plants. Serotonin's presence in insect venoms and plant spines serves to cause pain, which is a side-effect of serotonin injection. Serotonin is produced by pathogenic amoebae, causing diarrhea in the human gut. Its widespread presence in many seeds and fruits may serve to stimulate the digestive tract into expelling the seeds.
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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