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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (26)transporters (1) Show 27 proteins XML

enzymes (26)transporters (1) Show 27 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-11-15 21:04:29 UTC

HMDB ID

HMDB0000259

Secondary Accession Numbers

HMDB00259

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₀H₁₂N₂O

Average Molecular Weight

176.2151

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis

Psychiatric disorder

Schizophrenia

Genetic disorder

Inborn errors of metabolism

Aromatic l-amino acid decarboxylase deficiency - Reduced in human urine (PMID: 9686366 ).

Ingestion

Process

Naturally occurring process

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	25.5 mg/mL	Human Metabolome Project
LogP	0.21	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	147.57	30932474
[M-H]-	MetCCS_train_neg	135.85	30932474
[M+H]+	Baker	151.9	30932474
[M-H]-	Not Available	141.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000319
[M+H]+	Not Available	151.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000319

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.5 g/L	ALOGPS
logP	10^(0.56) g/L	ALOGPS
logP	10^(0.48) g/L	ChemAxon
logS	10^(-1.8) g/L	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.384	31661259
DarkChem	[M-H]-	138.73	31661259
AllCCS	[M+H]+	139.09	32859911
AllCCS	[M-H]-	139.937	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Serotonin	NCCC1=CNC2=C1C=C(O)C=C2	3251.5	Standard polar	33892256
Serotonin	NCCC1=CNC2=C1C=C(O)C=C2	2108.1	Standard non polar	33892256
Serotonin	NCCC1=CNC2=C1C=C(O)C=C2	2149.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Serotonin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2[NH]C=C(CCN)C2=C1	2027.7	Semi standard non polar	33892256
Serotonin,1TMS,isomer #2	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(O)C=C12	2204.6	Semi standard non polar	33892256
Serotonin,1TMS,isomer #3	C[Si](C)(C)N1C=C(CCN)C2=CC(O)=CC=C21	2111.6	Semi standard non polar	33892256
Serotonin,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2123.8	Semi standard non polar	33892256
Serotonin,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2282.8	Standard non polar	33892256
Serotonin,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2418.6	Standard polar	33892256
Serotonin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2080.7	Semi standard non polar	33892256
Serotonin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2154.9	Standard non polar	33892256
Serotonin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2397.9	Standard polar	33892256
Serotonin,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C	2350.8	Semi standard non polar	33892256
Serotonin,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C	2394.4	Standard non polar	33892256
Serotonin,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C	2606.9	Standard polar	33892256
Serotonin,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2221.8	Semi standard non polar	33892256
Serotonin,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2301.1	Standard non polar	33892256
Serotonin,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2462.2	Standard polar	33892256
Serotonin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2358.8	Semi standard non polar	33892256
Serotonin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2437.3	Standard non polar	33892256
Serotonin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2359.7	Standard polar	33892256
Serotonin,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2176.9	Semi standard non polar	33892256
Serotonin,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2274.2	Standard non polar	33892256
Serotonin,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2282.9	Standard polar	33892256
Serotonin,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2405.9	Semi standard non polar	33892256
Serotonin,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2510.1	Standard non polar	33892256
Serotonin,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2385.2	Standard polar	33892256
Serotonin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2447.1	Semi standard non polar	33892256
Serotonin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2437.7	Standard non polar	33892256
Serotonin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2265.5	Standard polar	33892256
Serotonin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCN)C2=C1	2312.3	Semi standard non polar	33892256
Serotonin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(O)C=C12	2446.9	Semi standard non polar	33892256
Serotonin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC(O)=CC=C21	2369.3	Semi standard non polar	33892256
Serotonin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2678.2	Semi standard non polar	33892256
Serotonin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2699.0	Standard non polar	33892256
Serotonin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2603.2	Standard polar	33892256
Serotonin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2570.0	Semi standard non polar	33892256
Serotonin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2547.8	Standard non polar	33892256
Serotonin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2542.8	Standard polar	33892256
Serotonin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2802.0	Semi standard non polar	33892256
Serotonin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2798.2	Standard non polar	33892256
Serotonin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2694.3	Standard polar	33892256
Serotonin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2693.4	Semi standard non polar	33892256
Serotonin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2724.6	Standard non polar	33892256
Serotonin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2597.3	Standard polar	33892256
Serotonin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3045.7	Semi standard non polar	33892256
Serotonin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3035.3	Standard non polar	33892256
Serotonin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	2644.3	Standard polar	33892256
Serotonin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2885.8	Semi standard non polar	33892256
Serotonin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2877.6	Standard non polar	33892256
Serotonin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2593.9	Standard polar	33892256
Serotonin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	3024.4	Semi standard non polar	33892256
Serotonin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	3079.7	Standard non polar	33892256
Serotonin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2637.4	Standard polar	33892256
Serotonin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3286.5	Semi standard non polar	33892256
Serotonin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3166.4	Standard non polar	33892256
Serotonin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2641.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-1900000000-461c2a1f67418e6b5d6a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-1900000000-2286e87324e9f4a78cb4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1900000000-927b865023cbba872101	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-8900000000-4b838943ace80c8b7734	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-6900000000-a7dd5c569cf4d085d244	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-MS (4 TMS)	splash10-00di-0900000000-2346e553f96cb980c8fc	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-MS (3 TMS)	splash10-00di-1900000000-01fbd5196188d4e0f21c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin EI-B (Non-derivatized)	splash10-0002-9800000000-9ce9fb2286c3b7ea7719	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-461c2a1f67418e6b5d6a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-2286e87324e9f4a78cb4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-927b865023cbba872101	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-1910000000-02c17b4cd3336a8bf9b1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-8900000000-4b838943ace80c8b7734	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-EI-TOF (Non-derivatized)	splash10-00di-6900000000-a7dd5c569cf4d085d244	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-MS (Non-derivatized)	splash10-00di-0900000000-2346e553f96cb980c8fc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Serotonin GC-MS (Non-derivatized)	splash10-00di-1900000000-01fbd5196188d4e0f21c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-6900000000-95a89ff8a3b12e7e8e25	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9450000000-52e0b628b7795c643362	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0900000000-6acaf73bcd452e24b886	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0aor-0900000000-259227b20b82e6362059	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-02e9-5900000000-2f58fbed270523182158	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin EI-B (HITACHI M-80) , Positive-QTOF	splash10-0002-9800000000-abcd0769bb17d07b3e38	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-03di-0900000000-bf65d809200ea387ebf5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-03xr-0900000000-a0b7d8a671909c6f4ad1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-014i-1900000000-fa80d05236eabbafd678	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-014i-4900000000-4e2e322d56fc9ee00edd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-004i-0900000000-c79f0b03a8dc1da0a10a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF	splash10-03fr-0900000000-9cb056cd56bae76589d0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin Linear Ion Trap , negative-QTOF	splash10-03di-1900000000-d64210214a1b3766ff6e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF , positive-QTOF	splash10-03di-0900000000-08840bc938c367dacbb2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF , positive-QTOF	splash10-03yi-0900000000-858936972fd87c0c0b14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF , positive-QTOF	splash10-0159-4900000000-a8fc7dff385a4f51b88a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QTOF , positive-QTOF	splash10-00p0-9400000000-7e4063d2b516ae59df84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ , positive-QTOF	splash10-03di-0900000000-bf65d809200ea387ebf5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ , positive-QTOF	splash10-03di-0900000000-8a171ac4fdc0474f7f48	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin LC-ESI-QQ , positive-QTOF	splash10-03xr-0900000000-a0b7d8a671909c6f4ad1	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 10V, Positive-QTOF	splash10-01t9-0900000000-a4e556450f24165aed15	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 20V, Positive-QTOF	splash10-03di-0900000000-657c360c251ec5745d1f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 40V, Positive-QTOF	splash10-01qc-2900000000-397a6873ea727da9cc8f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 10V, Negative-QTOF	splash10-004i-0900000000-253552852dde8abefca0	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 20V, Negative-QTOF	splash10-004i-0900000000-5dd492dfc2d781e72254	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Serotonin 40V, Negative-QTOF	splash10-053r-1900000000-bed3bfffbc9cca506281	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

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

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available
Benzocaine Action Pathway		Not Available
Bupivacaine Action Pathway		Not Available
Chloroprocaine Action Pathway		Not Available
Cocaine Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.85 +/- 0.077 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.07 (0-0.15) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.70 +/- 0.32 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.74 +/- 0.28 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.97 +/- 0.28 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.30-2.00 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.41 +/- 0.33 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	1.14(0.72-1.72) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0057-0.012 uM	Adult (>18 years old)	Not Specified	Normal	2580417	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0053-0.01 uM	Adult (>18 years old)	Not Specified	Normal	2580417	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.001 (0.0006-0.002) uM	Adult (>18 years old)	Both	Normal	12834252	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002-0.025 uM	Children (1-13 years old)	Male	Normal	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00001 +/- 0.000002 uM	Adult (>18 years old)	Male	Normal	8884658	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0059 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.026 (0.017-0.040) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.02 (0.004-0.0315) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.1512 +/- 0.0566 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.1-0.35 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.20 +/- 0.07 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.2 +/- 0.05 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	0.065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	9.892 +/- 3.264 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0110-0.0680 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	0.03 (0.015-0.046) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.08 (0.04-0.12) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0350-0.0670 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	9686366	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.61 +/- 0.096 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected and Quantified	1.4(0.96-1.98) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.002 uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00001 +/- 0.0000036 uM	Adult (>18 years old)	Not Specified	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0044 (0.00-0.0093) uM	Adult (>18 years old)	Both	Parkinson's Disease	12834252	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00001 +/- 0.000004 uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	0.1758 +/- 0.057 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.1782 +/- 0.0798 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	3.755 +/- 3.583 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.124-0.233 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details
Urine	Detected and Quantified	0.188 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	0.221 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Parkinson's disease
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. [PubMed:12834252 ]
Hypothyroidism
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. [PubMed:9849813 ]
Sepiapterin reductase deficiency
Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Aromatic L-amino acid decarboxylase deficiency
Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Brunner Syndrome
Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]

Associated OMIM IDs

181500 (Schizophrenia)
168600 (Parkinson's disease)
182125 (Sepiapterin reductase deficiency)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)
608643 (Aromatic L-amino acid decarboxylase deficiency)
300615 (Brunner Syndrome)

External Links

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

VMH ID

SRTN

MarkerDB ID

MDB00000126

Good Scents ID

Not Available

References

Synthesis Reference

Harley-Mason, John; Jackson, A. H. Hydroxytryptamines. I. Bufotenine, 6-hydroxybufotenine, and serotonin. Journal of the Chemical Society (1954), 1165-71.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:16842443 ]
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. [PubMed:12834252 ]
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 ]
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. Epub 2006 Jan 18. [PubMed:16412483 ]
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. [PubMed:9849813 ]
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. [PubMed:8884658 ]
Serebruany VL, Glassman AH, Malinin AI, Nemeroff CB, Musselman DL, van Zyl LT, Finkel MS, Krishnan KR, Gaffney M, Harrison W, Califf RM, O'Connor CM: Platelet/endothelial biomarkers in depressed patients treated with the selective serotonin reuptake inhibitor sertraline after acute coronary events: the Sertraline AntiDepressant Heart Attack Randomized Trial (SADHART) Platelet Substudy. Circulation. 2003 Aug 26;108(8):939-44. Epub 2003 Aug 11. [PubMed:12912814 ]
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 ]
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. [PubMed:1691117 ]
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. [PubMed:10367709 ]
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. Epub 2005 Oct 21. [PubMed:16580588 ]
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. Epub 2005 Nov 10. [PubMed:16289360 ]
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. [PubMed:2580417 ]
Lawrence KR, Adra M, Gillman PK: Serotonin toxicity associated with the use of linezolid: a review of postmarketing data. Clin Infect Dis. 2006 Jun 1;42(11):1578-83. Epub 2006 Apr 27. [PubMed:16652315 ]
Blardi P, de Lalla A, Pieragalli D, De Franco V, Meini S, Ceccatelli L, Auteri A: Effect of iloprost on plasma asymmetric dimethylarginine and plasma and platelet serotonin in patients with peripheral arterial occlusive disease. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):175-82. Epub 2006 Jul 18. [PubMed:16939882 ]
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. Epub 2006 Mar 2. [PubMed:16515859 ]
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. [PubMed:16435178 ]
Ortiz J, Artigas F, Gelpi E: Serotonergic status in human blood. Life Sci. 1988;43(12):983-90. [PubMed:2459577 ]
Sato T, Suzuki E, Yokoyama M, Semba J, Watanabe S, Miyaoka H: Chronic intraperitoneal injection of interferon-alpha reduces serotonin levels in various regions of rat brain, but does not change levels of serotonin transporter mRNA, nitrite or nitrate. Psychiatry Clin Neurosci. 2006 Aug;60(4):499-506. [PubMed:16884454 ]
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. Epub 2006 Mar 3. [PubMed:16516555 ]
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Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. [PubMed:24621061 ]

Only showing the first 10 proteins. There are 27 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Serotonin N-acetyltransferase

General function:: Involved in N-acetyltransferase activity
Specific function:: Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:: AANAT
Uniprot ID:: Q16613
Molecular weight:: 23343.8

Reactions

Acetyl-CoA + Serotonin → Coenzyme A + N-Acetylserotonin	details

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

4. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Reactions

5-Hydroxy-L-tryptophan → Serotonin + CO(2)	details
5-Hydroxy-L-tryptophan → Serotonin + Carbon dioxide	details

Enzyme Details

5. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Enzyme Details

6. Indolethylamine N-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:: INMT
Uniprot ID:: O95050
Molecular weight:: 28833.695

Reactions

S-Adenosylmethionine + Serotonin → S-Adenosylhomocysteine + N-Methylserotonin	details

Enzyme Details

7. Indoleamine 2,3-dioxygenase 1

General function:: Involved in heme binding
Specific function:: Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:: IDO1
Uniprot ID:: P14902
Molecular weight:: 45325.89

Reactions

Serotonin + Oxygen → Formyl-5-hydroxykynurenamine	details

Enzyme Details

8. Protein arginine N-methyltransferase 3

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:: PRMT3
Uniprot ID:: O60678
Molecular weight:: 59902.7

Enzyme Details

9. 5-hydroxytryptamine receptor 4

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:: HTR4
Uniprot ID:: Q13639
Molecular weight:: 43761.0

Enzyme Details

10. 5-hydroxytryptamine receptor 7

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:: HTR7
Uniprot ID:: P34969
Molecular weight:: 53554.4

Transporters

Enzyme Details

1. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

Only showing the first 10 proteins. There are 27 proteins in total.

Show all enzymes and transporters

Showing metabocard for Serotonin (HMDB0000259)

MOL for HMDB0000259 (Serotonin)

3D MOL for HMDB0000259 (Serotonin)

3D SDF for HMDB0000259 (Serotonin)

3D-SDF for HMDB0000259 (Serotonin)

PDB for HMDB0000259 (Serotonin)

3D PDB for HMDB0000259 (Serotonin)

SMILES for HMDB0000259 (Serotonin)

INCHI for HMDB0000259 (Serotonin)

Structure for HMDB0000259 (Serotonin)

3D Structure for HMDB0000259 (Serotonin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters