Np mrd loader

Showing NP-Card for Serotonin (NP0000608)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:26 UTC
NP-MRD IDNP0000608
Secondary Accession NumbersNone
Natural Product Identification
Common NameSerotonin
DescriptionSerotonin 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000608 (Serotonin)


  Mrv1652311131919232D          

 13 14  0  0  0  0            999 V2000
    5.4222   -4.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7077   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -3.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222   -3.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7077   -3.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -3.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -4.5546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4062   -3.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933   -3.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1762   -2.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9833   -2.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2382   -1.4790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  7  1  0  0  0  0
  4  1  1  0  0  0  0
  3  4  2  0  0  0  0
  4  8  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  2  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000608 (Serotonin)

HMDB0000259
     RDKit          3D
Serotonin
 25 26  0  0  0  0  0  0  0  0999 V2000
   -3.0826   -0.0724    0.8919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437    0.7948   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    0.0129   -1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6662   -0.7518   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.1027   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -2.3629    0.1469 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618   -1.2199    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437   -0.9342    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    0.3738    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    1.4021    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067    2.6719    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151    1.0777   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473   -0.2182   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747    0.4419    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3668   -0.2023    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    1.2804   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9157    1.5971    0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134   -0.6228   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.7480   -1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -2.8149   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9713   -3.3188    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923   -1.7144    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    0.5561    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543    3.4976   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931    1.8809   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
M  END
Download

3D SDF for NP0000608 (Serotonin)


  Mrv1652311131919232D          

 13 14  0  0  0  0            999 V2000
    5.4222   -4.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7077   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -3.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1367   -4.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222   -3.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7077   -3.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -3.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -4.5546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4062   -3.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933   -3.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1762   -2.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9833   -2.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2382   -1.4790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  7  1  0  0  0  0
  4  1  1  0  0  0  0
  3  4  2  0  0  0  0
  4  8  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  2  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000608

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H12N2O

> <MOLECULAR_WEIGHT>
176.2151

> <EXACT_MASS>
176.094963016

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.313416912562396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-aminoethyl)-1H-indol-5-ol

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.48154800923293156

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.223535339159515

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.314034178077875

> <JCHEM_PKA_STRONGEST_BASIC>
10.004289627293197

> <JCHEM_POLAR_SURFACE_AREA>
62.040000000000006

> <JCHEM_REFRACTIVITY>
52.3538

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
serotonin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000608 (Serotonin)

HMDB0000259
     RDKit          3D
Serotonin
 25 26  0  0  0  0  0  0  0  0999 V2000
   -3.0826   -0.0724    0.8919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437    0.7948   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    0.0129   -1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6662   -0.7518   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.1027   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -2.3629    0.1469 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618   -1.2199    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437   -0.9342    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    0.3738    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    1.4021    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067    2.6719    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151    1.0777   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473   -0.2182   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747    0.4419    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3668   -0.2023    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    1.2804   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9157    1.5971    0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134   -0.6228   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.7480   -1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -2.8149   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9713   -3.3188    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923   -1.7144    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    0.5561    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543    3.4976   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931    1.8809   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
M  END
Download

PDB for NP0000608 (Serotonin)

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
Download

3D PDB for NP0000608 (Serotonin)

COMPND    HMDB0000259
HETATM    1  N1  UNL     1      -3.083  -0.072   0.892  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.544   0.795  -0.140  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.810   0.013  -1.206  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.666  -0.752  -0.637  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.561  -2.103  -0.369  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.657  -2.363   0.147  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.362  -1.220   0.227  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.644  -0.934   0.678  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.083   0.374   0.630  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.282   1.402   0.147  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.807   2.672   0.139  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.015   1.078  -0.291  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.547  -0.218  -0.257  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.875   0.442   1.343  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.367  -0.202   1.668  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.408   1.280  -0.644  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.916   1.597   0.264  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.513  -0.623  -1.748  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.387   0.748  -1.918  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.367  -2.815  -0.563  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.971  -3.319   0.428  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.292  -1.714   1.061  1.00  0.00           H  
HETATM   23  H10 UNL     1       4.089   0.556   0.991  1.00  0.00           H  
HETATM   24  H11 UNL     1       2.354   3.498  -0.176  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.393   1.881  -0.668  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5    5   13
CONECT    5    6   20
CONECT    6    7   21
CONECT    7    8    8   13
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   12
CONECT   11   24
CONECT   12   13   13   25
END
Download

SMILES for NP0000608 (Serotonin)

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

INCHI for NP0000608 (Serotonin)

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
Download
View in JSmol
Synonyms
ValueSource
3-(2-Aminoethyl)-1H-indol-5-olChEBI
5-HTChEBI
5-HydroxytryptamineChEBI
EnteramineChEBI
SerotonineChEBI
ThrombocytinChEBI
ThrombotoninChEBI
HippophaineHMDB
HydroxytryptamineHMDB
5 HydroxytryptamineHMDB
3-(2-Aminoethyl)indol-5-olHMDB
3-(b-Aminoethyl)-5-hydroxyindoleHMDB
5-HTAHMDB
5-Hydroxy-3-(b-aminoethyl)indoleHMDB
5-Hydroxy-tryptamineHMDB
5-HydroxyltryptamineHMDB
5-HydroxytriptamineHMDB
AntemovisHMDB
DS SubstanceHMDB
EnteraminHMDB
Chemical FormulaC10H12N2O
Average Mass176.2151 Da
Monoisotopic Mass176.09496 Da
IUPAC Name3-(2-aminoethyl)-1H-indol-5-ol
Traditional Nameserotonin
CAS Registry Number50-67-9
SMILES
NCCC1=CNC2=CC=C(O)C=C12
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 KeyQZAYGJVTTNCVMB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acetabularia acetabulumKNApSAcK Database
Actinidia chinensisFooDB
Agastaches rugosa-
Albizia julibrissinKNApSAcK Database
Aloe velaKNApSAcK Database
Amanita citrinaLOTUS Database
Amorphophallus konjacLOTUS Database
Amorphophallus konjac K.KochKNApSAcK Database
Ananas comosusKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Andrographis paniculatusKNApSAcK Database
Angelica biserrataKNApSAcK Database
Angelica sinensisKNApSAcK Database
Anser anserFooDB
Aplysia californicaLOTUS Database
Arabidopsis thalianaLOTUS Database
Araujia sericiferaLOTUS Database
Arnebia euchromaKNApSAcK Database
Artemisis anna-
Babreum coscluea-
Beta vulgarisKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica rapaFooDB
Bubalus bubalisFooDB
Bufo gargarizansAnimalia
Capra aegagrus hircusFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
Ceratium horridum-
CervidaeFooDB
Cervus canadensisFooDB
Chenopodium rubrumKNApSAcK Database
Chlomydomonas spp.-
Chrysanthemum x morifoliumPlant
Cistanche deseriocolaKNApSAcK Database
Citrus reticulataKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Coptis chinensisKNApSAcK Database
Coruns officinalis-
Cucumis sativusKNApSAcK Database
Cucumis sativus L.Plant
Curcuma aeruginosaKNApSAcK Database
Datura metelPlant
Dendranthema morifoliumKNApSAcK Database
Desmodium styracifoliumKNApSAcK Database
Didymosphaeria mori-albae-
Dromaius novaehollandiaeFooDB
Dunaliella teriolectaKNApSAcK Database
Epimedium brevicornumKNApSAcK Database
Equus caballusFooDB
Eucommia ulmoidesKNApSAcK Database
Forsythia suspensaKNApSAcK Database
Galdenia jasminoides-
Gallus gallusFooDB
Gekko japanicus-
Gentiana macrophyllaKNApSAcK Database
Gentiana scabraKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Gonyaulax polyedra-
GossypiumFooDB
Gossypium hirsutumKNApSAcK Database
Grona styracifoliaPlant
Hippophae rhamnoidesKNApSAcK Database
Hyacinthoides non-scriptaLOTUS Database
Hypericum perforatumKNApSAcK Database
Hyrtios reticulatus-
Ipomoea nilPlant
Isatis indigoticaKNApSAcK Database
Isatis tinctoriaPlant
Juglans nigra L.FooDB
Juglans regiaFooDB
Juglans regia ssp. FallaxKNApSAcK Database
Juglans sieboldianaKNApSAcK Database
Lagopus mutaFooDB
Laminaria digitataKNApSAcK Database
Lemna aequinoctialisLOTUS Database
Leonurus japonicusKNApSAcK Database
LeporidaeFooDB
Lepus timidusFooDB
Litoria verreauxiiLOTUS Database
Lobelia chinensisKNApSAcK Database
Lonicera japonicaKNApSAcK Database
Lophartherum gracile-
Lupinus albusKNApSAcK Database
Lycium barbarumKNApSAcK Database
Mahania bealei-
Mamestra brassicaeLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mimosa somniansLOTUS Database
Mimosa zimapanensisKNApSAcK Database
Momordica charantiaFooDB
Morus albaKNApSAcK Database
Mucuna pruriensKNApSAcK Database
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa paradisiaca Linn.KNApSAcK Database
Musa sapientumKNApSAcK Database
Musa spp.KNApSAcK Database
Musa x paradisiacaFooDB
Nicotiana tobacumKNApSAcK Database
Nitraria schoberiLOTUS Database
Noctiluca scintillans-
Numida meleagrisFooDB
OdocoileusFooDB
Ophiopogon japonicusKNApSAcK Database
OryctolagusFooDB
Ovis ariesFooDB
Panaeolus cyanescensLOTUS Database
Panaeolus papilionaceusLOTUS Database
Panax notoginsnegKNApSAcK Database
Paramuricea clavataLOTUS Database
Patrinia scabiosifoliaKNApSAcK Database
Patriniae scabiosaefoliae-
Peganum harmalaLOTUS Database
Periostracum cicadae-
Persea americanaFooDB
Petalonia fascia-
Pharbitis nilKNApSAcK Database
Phaseolus coccineusKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron amurenseKNApSAcK Database
Pheretima aspergillum-
Phoenix dactyliferaFooDB
Pirola decorata-
Pisum sativumKNApSAcK Database
Polygala tenuifoliaKNApSAcK Database
Polygonatum sibiricumKNApSAcK Database
Polygonum multiflorumKNApSAcK Database
Prunella vulgarisKNApSAcK Database
Prunus cerasusKNApSAcK Database
Prunus domesticaFooDB
Prunus persicaFooDB
Pterygophora californica-
Pueraria lobataKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrocystis lunula-
Ranunculus sceleratusLOTUS Database
Raphanus sativusKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Rheum palmatumKNApSAcK Database
Rubus chingiiKNApSAcK Database
Salvia miltiorrhizaKNApSAcK Database
Samanea samanKNApSAcK Database
Saposhmikovia divaricata-
Schisondra chinensis-
Scrophularia ningpoensisKNApSAcK Database
Scutellaria amoenaKNApSAcK Database
Scutellaria baicalensisKNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumFooDB
Sophora flavescensKNApSAcK Database
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumKNApSAcK Database
Tanacetum partheniumKNApSAcK Database
Taxillus chinensisKNApSAcK Database
Theobroma cacaoFooDB
Tovaria pendulaLOTUS Database
Trypanosoma bruceiLOTUS Database
Trypanosoma cruzi-
Uncaria rhynchophyllaKNApSAcK Database
Urtica dioicaKNApSAcK Database
Viola philipicaKNApSAcK Database
VitisFooDB
Wolfiporia cocos-
Zea mays L.FooDB
Ziziphus jujubaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Alexandrium lusitanicumKNApSAcK Database
Amphidinium carteraeKNApSAcK Database
Bombyx batryticatusKNApSAcK Database
Bufo bufo gargarizansKNApSAcK Database
Chondrus crispusKNApSAcK Database
Cliona delitrixKNApSAcK Database
Erythrobacter longusKNApSAcK Database
Euglena gracilisKNApSAcK Database
Gracilaria tenustipitataKNApSAcK Database
Neurospora crassaKNApSAcK Database
Palmaria palmataKNApSAcK Database
Porphyra umbilicalisKNApSAcK Database
Rattus sp.KNApSAcK Database
Rhodospirillum rubrumKNApSAcK Database
Saccharomyces cerevisiaeKNApSAcK Database
Scolopendra subspinipesKNApSAcK Database
Tetrahymena thermophilaKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility25.5 mg/mLWishart, D. S., Tzur, D., Knox, C., Eisner, R., Guo, A. C., Young, N., ... & Querengesser, L. (2007). HMDB: the human metabolome database. Nucleic acids research, 35(suppl_1), D521-D526.
LogP0.21Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2.5 g/LALOGPS
logP0.56ALOGPS
logP0.48ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area62.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.35 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000259
DrugBank IDDB08839
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012158
KNApSAcK IDC00001429
Chemspider ID5013
KEGG Compound IDC00780
BioCyc IDSEROTONIN
BiGG IDNot Available
Wikipedia LinkSerotonin
METLIN IDNot Available
PubChem Compound5202
PDB IDNot Available
ChEBI ID28790
Good Scents IDrw1628941
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. Ortiz J, Artigas F, Gelpi E: Serotonergic status in human blood. Life Sci. 1988;43(12):983-90. [PubMed:2459577 ]
  19. 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 ]
  20. 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 ]
  21. De-Miguel FF, Trueta C: Synaptic and extrasynaptic secretion of serotonin. Cell Mol Neurobiol. 2005 Mar;25(2):297-312. [PubMed:16047543 ]