MiMeDB: Showing metabocard for Serotonin (MMDBc0047905)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:15 UTC

Update Date

2024-10-09 21:25:47 UTC

Metabolite ID

MMDBc0047905

Metabolite Identification

Common Name

Serotonin

Description

Serotonin or 5-hydroxytryptamine (5-HT) is a molecule that belongs to the class of compounds known as indoleamines. An indoleamine consists of an indole ring that bears an amino group or an alkyl amino group attached to the indole ring. Serotonin has an aminoethyl at position 2 and a hydroxyl group at position 5 of the indole ring. Serotonin exists in all living organisms, ranging from bacteria to plants to humans. In mammals, serotonin functions as a monoamine neurotransmitter, a biochemical messenger and regulator. It is synthesized from the essential amino acid L-Tryptophan. Approximately 90% of the human body's total serotonin is located in the enterochromaffin cells in the GI tract, where it regulates intestinal movements. About 8% is found in platelets and 1-2% in the CNS. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns, including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state, sexual behavior, and others. Deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543 ). Serotonin is also a microbial metabolite that can be found in the feces and urine of mammals. Urinary serotonin is produced by Candida, Streptococcus, Escherichia, and Enterococcus (PMID: 24621061 ). In plants, serotonin was first found and reported in a legume called Mucuna pruriens. The greatest concentration of serotonin in plants has been found in walnuts and hickory. In pineapples, banana, kiwi fruit, plums and tomatoes the concentration of serotonin is around 3 to 30 mg/kg.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 13-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-19         0                                  
HETATM    1  C   UNK     0      10.121  -8.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788  -8.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.455  -6.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.455  -8.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.121  -5.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  -6.486   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.920  -6.010   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      12.920  -8.502   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.825  -7.256   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.454  -5.716   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.396  -4.546   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.902  -4.225   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      15.378  -2.761   0.000  0.00  0.00           N+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    7    4    5                                                  
CONECT    4    1    3    8                                                  
CONECT    5    3    6                                                       
CONECT    6    5    2   10                                                  
CONECT    7    3    9   11                                                  
CONECT    8    4    9                                                       
CONECT    9    7    8                                                       
CONECT   10    6                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
3-(2-Aminoethyl)-1H-indol-5-ol	ChEBI
5-HT	ChEBI
5-Hydroxytryptamine	ChEBI
Enteramine	ChEBI
Serotonine	ChEBI
Thrombocytin	ChEBI
Thrombotonin	ChEBI
Hippophaine	HMDB
Hydroxytryptamine	HMDB
5 Hydroxytryptamine	HMDB
3-(2-Aminoethyl)indol-5-ol	HMDB
3-(b-Aminoethyl)-5-hydroxyindole	HMDB
5-HTA	HMDB
5-Hydroxy-3-(b-aminoethyl)indole	HMDB
5-Hydroxy-tryptamine	HMDB
5-Hydroxyltryptamine	HMDB
5-Hydroxytriptamine	HMDB
Antemovis	HMDB
DS Substance	HMDB
Enteramin	HMDB

Molecular Formula

C₁₀H₁₂N₂O

Average Mass

176.2151

Monoisotopic Mass

176.094963016

IUPAC Name

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

Traditional Name

serotonin

CAS Registry Number

50-67-9

SMILES

NCCC1=CNC2=C1C=C(O)C=C2

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

Chemical Taxonomy

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-1900000000-461c2a1f67418e6b5d6a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-1900000000-2286e87324e9f4a78cb4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1900000000-927b865023cbba872101	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-8900000000-4b838943ace80c8b7734	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-6900000000-a7dd5c569cf4d085d244	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00di-0900000000-2346e553f96cb980c8fc	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-1900000000-01fbd5196188d4e0f21c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9800000000-9ce9fb2286c3b7ea7719	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-461c2a1f67418e6b5d6a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-2286e87324e9f4a78cb4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-927b865023cbba872101	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-8900000000-4b838943ace80c8b7734	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-6900000000-a7dd5c569cf4d085d244	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-0900000000-2346e553f96cb980c8fc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-1900000000-01fbd5196188d4e0f21c	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-6900000000-95a89ff8a3b12e7e8e25	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9450000000-52e0b628b7795c643362	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-1900000000-d64210214a1b3766ff6e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-66be80bf04de85d374b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-662e21ddee556bb4a222	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-337ec7823cec887c8ad3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8ac1f8742228b0c2ada5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00os-4900000000-fe28a76e9223ea9c3912	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-faf92490b8049363f990	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-c65e4440ede6c6f45d71	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-6acaf73bcd452e24b886	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-0900000000-259227b20b82e6362059	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02e9-5900000000-2f58fbed270523182158	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0002-9800000000-abcd0769bb17d07b3e38	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-0900000000-bf65d809200ea387ebf5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03xr-0900000000-a0b7d8a671909c6f4ad1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014i-1900000000-fa80d05236eabbafd678	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-4900000000-4e2e322d56fc9ee00edd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-c79f0b03a8dc1da0a10a	2012-08-31	View Spectrum
LC-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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-08840bc938c367dacbb2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03yi-0900000000-858936972fd87c0c0b14	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0159-4900000000-a8fc7dff385a4f51b88a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00p0-9400000000-7e4063d2b516ae59df84	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-bf65d809200ea387ebf5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2017-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191706	Serotonin N-acetyltransferase	Enzyme	Q16613	Homo sapiens
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo sapiens
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo sapiens
MMDBp0192028	Aldo-keto reductase family 1 member C3	Unknown	P42330	Homo sapiens
MMDBp0192081	Indolethylamine N-methyltransferase	Unknown	O95050	Homo sapiens
MMDBp0192103	Indoleamine 2,3-dioxygenase 1	Unknown	P14902	Homo sapiens
MMDBp0192132	Protein arginine N-methyltransferase 3	Unknown	O60678	Homo sapiens
MMDBp0193439	Sodium-dependent serotonin transporter	Transporter	P31645	Homo sapiens
MMDBp0193458	5-hydroxytryptamine receptor 4	Enzyme	Q13639	Homo sapiens
MMDBp0193480	5-hydroxytryptamine receptor 7	Enzyme	P34969	Homo sapiens
MMDBp0193490	Transcription factor Sp1	Unknown	P08047	Homo sapiens
MMDBp0193517	5-hydroxytryptamine receptor 2B	Unknown	P41595	Homo sapiens
MMDBp0193525	5-hydroxytryptamine receptor 1B	Enzyme	P28222	Homo sapiens
MMDBp0193548	5-hydroxytryptamine receptor 1F	Enzyme	P30939	Homo sapiens
MMDBp0193584	5-hydroxytryptamine receptor 1A	Enzyme	P08908	Homo sapiens
MMDBp0193630	5-hydroxytryptamine receptor 2A	Unknown	P28223	Homo sapiens
MMDBp0193729	5-hydroxytryptamine receptor 3A	Enzyme	P46098	Homo sapiens
MMDBp0193739	5-hydroxytryptamine receptor 1D	Enzyme	P28221	Homo sapiens
MMDBp0194191	Indoleamine 2,3-dioxygenase 2	Unknown	Q6ZQW0	Homo sapiens
MMDBp0196387	5-hydroxytryptamine receptor 3B	Unknown	O95264	Homo sapiens
MMDBp0196388	5-hydroxytryptamine receptor 1E	Unknown	P28566	Homo sapiens
MMDBp0196389	5-hydroxytryptamine receptor 5A	Unknown	P47898	Homo sapiens
MMDBp0196837	HemK methyltransferase family member 1	Unknown	Q9Y5R4
MMDBp0196881	Methyltransferase-like protein 2B	Unknown	Q6P1Q9
MMDBp0196882	Methyltransferase-like protein 6	Unknown	Q8TCB7
MMDBp0197020	Uncharacterized methyltransferase WBSCR22	Unknown	O43709

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000114	5-Hydroxy-L-tryptophan	Serotonin	Not Available	VMH	1540578
MMDBr0000118	Serotonin	5-Hydroxyindoleacetaldehyde	monoamine oxidase A	VMH; KEGG	11134050 15035803 8920635 9653080
MMDBr0002167	Serotonin	Formyl-5-hydroxykynurenamine	indoleamine 2,3-dioxygenase 1	VMH	1061163
MMDBr0002168	Serotonin	N-Acetylserotonin	aralkylamine N-acetyltransferase	VMH	8661026
MMDBr0002169	S-Adenosylmethionine	S-Adenosylhomocysteine	indolethylamine N-methyltransferase	VMH	30371894
MMDBr0004179	Formaldehyde	6-Hydroxy-1,2,3,4-Tetrahydro-Beta-Carboline	Not Available	VMH	8891913

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aromatic l-amino acid decarboxylase deficiency	Increased	Association	Human Urine	HMDB	9686366
Hypothyroidism	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	9849813
Parkinson's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12834252
Schizophrenia	Decreased	Association	Human Blood	HMDB	25004141
Sepiapterin reductase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	18502672
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	89	Human feces; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	207	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	86	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	6	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Plant		Solanum melongena	FooDB	31437929
Plant	Bark	Hippophae rhamnoides	FooDB	31437929
Plant	Embryo	Juglans regia	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Plant	Carica papaya	FooDB	31437929
Plant	Fruit juice	Punica granatum	FooDB	31437929
Plant	Leaves	Pisum sativum	FooDB	31437929
Plant	Fruit	Prunus domestica	FooDB	31437929
Plant	Embryo	Juglans nigra	FooDB	31437929
Plant	Seed	Punica granatum	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Fruit	Hippophae rhamnoides	FooDB	31437929
Plant	Fruit	Gossypium	FooDB	31437929
Plant	Seed	Juglans regia	FooDB	31437929
Plant		Musa x paradisiaca	FooDB	31437929
Plant	Fruit	Solanum melongena	FooDB	31437929
Plant		Solanum lycopersicum	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant		Pisum sativum	FooDB	31437929
Plant	Fruit	Persea americana	FooDB	31437929
Plant	Fruit	Ananas comosus	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Actinidia chinensis	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant		Prunus persica	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Beta vulgaris var. rubra	FooDB	31437929
Plant		Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant		Prunus tomentosa	FooDB	31437929
Plant		Ananas comosus	FooDB	31437929
Plant		Ananas comosus	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Capsicum annuum var. annuum	FooDB	31437929
Plant		Brassica rapa	FooDB	31437929
Plant	Plant	Theobroma cacao	FooDB	31437929
Plant		Musa acuminata	FooDB	31437929
Plant	Seed	Theobroma cacao	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Daucus carota ssp. sativus	FooDB	31437929
Plant	Fruit	Momordica charantia	FooDB	31437929
Plant	Fruit	Solanum tuberosum	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant	Fruit	Phoenix dactylifera	FooDB	31437929
Plant	Fruit	Musa x paradisiaca	FooDB	31437929
Plant		Phaseolus coccineus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.188				umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	0.221				umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified			0.124	0.233	umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	HMDB	8503438
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00001	0.0000036			uM	Adult (>18 years old)	Not Specified	Hypothyroidism	HMDB	9849813
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00001	0.000004			uM	Adult (>18 years old)	Both	Hypothyroidism	HMDB	9849813
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0044		0.00	0.0093	uM	Adult (>18 years old)	Both	Parkinson's Disease	HMDB	12834252
Human Blood	Detected and Quantified	0.61	0.096			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	25004141
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.002				uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	HMDB	18502672
Human Urine	Detected and Quantified	0.065				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00001	0.000002			uM	Adult (>18 years old)	Male	Normal	HMDB	8884658
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.001		0.0006	0.002	uM	Adult (>18 years old)	Both	Normal	HMDB	12834252
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.002	0.025	uM	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0053	0.01	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	2580417
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0057	0.012	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	2580417
Human Urine	Detected and Quantified			0.0110	0.0680	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	8503438
Human Urine	Detected and Quantified			0.0350	0.0670	umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Urine	Detected and Quantified	0.08		0.04	0.12	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			0.1	0.35	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.2	0.05			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.20	0.07			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.41	0.33			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	0.85	0.077			uM	Adult (>18 years old)	Both	Normal	HMDB	25004141
Human Blood	Detected and Quantified	1.14		0.72	1.72	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Urine	Detected and Quantified	0.1758	0.057			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.755	3.583			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.1512	0.0566			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	9.892	3.264			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0059				uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.02		0.004	0.0315	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.026		0.017	0.040	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.03		0.015	0.046	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.07		0	0.15	uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.70	0.32			uM	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.74	0.28			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.97	0.28			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified			0.30	2.00	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal medulla	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26476344
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000259

DrugBank ID

DB08839

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Serotonin

METLIN ID

Not Available

PubChem Compound

5202

PDB ID

Not Available

ChEBI ID

28790

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Lincoln J, Crowe R, Kamm MA, Burnstock G, Lennard-Jones JE: Serotonin and 5-hydroxyindoleacetic acid are increased in the sigmoid colon in severe idiopathic constipation. Gastroenterology. 1990 May;98(5 Pt 1):1219-25. doi: 10.1016/0016-5085(90)90336-y. [PubMed:1691117 ]
Ortiz J, Artigas F, Gelpi E: Serotonergic status in human blood. Life Sci. 1988;43(12):983-90. doi: 10.1016/0024-3205(88)90543-7. [PubMed:2459577 ]
Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. doi: 10.1111/j.1600-0404.1985.tb03176.x. [PubMed:2580417 ]
Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. doi: 10.1016/0022-3956(96)00007-6. [PubMed:8884658 ]
Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. doi: 10.1530/eje.0.1390493. [PubMed:9849813 ]
Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. [PubMed:9931050 ]
Lundeberg L, Liang Y, Sundstrom E, Nordlind K, Verhofstad A, Liden S, Johansson O: Serotonin in human allergic contact dermatitis. An immunohistochemical and high-performance liquid chromatographic study. Arch Dermatol Res. 1999 May;291(5):269-74. doi: 10.1007/s004030050407. [PubMed:10367709 ]
Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. doi: 10.1023/a:1024255208563. [PubMed:12834252 ]
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De-Miguel FF, Trueta C: Synaptic and extrasynaptic secretion of serotonin. Cell Mol Neurobiol. 2005 Mar;25(2):297-312. doi: 10.1007/s10571-005-3061-z. [PubMed:16047543 ]
Lommatzsch M, Hornych K, Zingler C, Schuff-Werner P, Hoppner J, Virchow JC: Maternal serum concentrations of BDNF and depression in the perinatal period. Psychoneuroendocrinology. 2006 Apr;31(3):388-94. doi: 10.1016/j.psyneuen.2005.09.003. Epub 2005 Nov 10. [PubMed:16289360 ]
Preuss HG, Garis RI, Bramble JD, Bagchi D, Bagchi M, Rao CV, Satyanarayana S: Efficacy of a novel calcium/potassium salt of (-)-hydroxycitric acid in weight control. Int J Clin Pharmacol Res. 2005;25(3):133-44. [PubMed:16366421 ]
King BM: The rise, fall, and resurrection of the ventromedial hypothalamus in the regulation of feeding behavior and body weight. Physiol Behav. 2006 Feb 28;87(2):221-44. doi: 10.1016/j.physbeh.2005.10.007. Epub 2006 Jan 18. [PubMed:16412483 ]
Ormazabal A, Vilaseca MA, Perez-Duenas B, Lambruschini N, Gomez L, Campistol J, Artuch R: Platelet serotonin concentrations in PKU patients under dietary control and tetrahydrobiopterin treatment. J Inherit Metab Dis. 2005;28(6):863-70. doi: 10.1007/s10545-005-0153-3. [PubMed:16435178 ]
Eriksson O, Wall A, Marteinsdottir I, Agren H, Hartvig P, Blomqvist G, Langstrom B, Naessen T: Mood changes correlate to changes in brain serotonin precursor trapping in women with premenstrual dysphoria. Psychiatry Res. 2006 Mar 31;146(2):107-16. doi: 10.1016/j.pscychresns.2005.02.012. Epub 2006 Mar 2. [PubMed:16515859 ]
Konca K, Tiftik EN, Aslan G, Kanik A, Yalcin A: The effect of cromoglycate on time-dependent histamine and serotonin concentrations in stored blood products. Transfus Apher Sci. 2006 Apr;34(2):193-8. doi: 10.1016/j.transci.2005.12.001. Epub 2006 Mar 3. [PubMed:16516555 ]
Blardi P, Palazzuoli A, de Lalla A, Auteri A: Variations of peripheral markers of serotoninergic system in selected vascular patients. Nutr Metab Cardiovasc Dis. 2006 Apr;16(3):210-4. doi: 10.1016/j.numecd.2005.05.008. Epub 2005 Oct 21. [PubMed:16580588 ]
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Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. doi: 10.1111/j.1365-2893.2005.00706.x. [PubMed:16842443 ]
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Showing metabocard for Serotonin (MMDBc0047905)

MOL for #<Metabolite:0x00007f46e5f69b08>

3D MOL for #<Metabolite:0x00007f46e5f69b08>

3D SDF for #<Metabolite:0x00007f46e5f69b08>

3D-SDF for #<Metabolite:0x00007f46e5f69b08>

PDB for #<Metabolite:0x00007f46e5f69b08>

3D PDB for #<Metabolite:0x00007f46e5f69b08>

SMILES for #<Metabolite:0x00007f46e5f69b08>

INCHI for #<Metabolite:0x00007f46e5f69b08>

Structure for #<Metabolite:0x00007f46e5f69b08>

3D Structure for #<Metabolite:0x00007f46e5f69b08>