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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:29 UTC

HMDB ID

HMDB0001238

Secondary Accession Numbers

HMDB0061066
HMDB01238
HMDB61066

Metabolite Identification

Common Name

N-Acetylserotonin

Description

N-Acetylserotonin (NAS), also known as normelatonin, is a naturally occurring chemical precursor and intermediate in the endogenous production of melatonin from serotonin. It also has biological activity in its own right, including acting as a melatonin receptor agonist, an agonist of the TrkB, and having antioxidant effects. N-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152 , 11103901 , 10721079 , 10591054 ). N-Acetylserotonin acts as a potent antioxidant, NAS effectiveness as an anti-oxidant has been found to be different depending on the experimental model used, it has been described as being between 5 and 20 times more effect than melatonin at protecting against oxidant damage. NAS has been shown to protect against lipid peroxidation in microsomes and mitochondria. NAS has also been reported to lower resting levels of ROS in peripheral blood lymphocytes and to exhibit anti-oxidant effects against t-butylated hydroperoxide- and diamide-induced ROS.

Structure

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

HMDB0001238
     RDKit          3D
N-Acetylserotonin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -5.1424    0.4211   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    0.4261   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363    0.3325    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    0.5300   -1.0283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5282   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094   -0.7309   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.0039    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -2.2301    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1132   -2.2413    1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.0785    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -0.6029    0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791    0.6618    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.4468   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    2.7273   -0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014    0.9417   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335   -0.3001    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3794    0.7011   -1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6841    1.0815    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5978   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868    0.6095   -2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.4204   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.7046   -1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -0.9281    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203   -1.5637   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -3.0839    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424   -3.0572    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913   -1.2583    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028    1.0588    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3598    3.5405   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309    1.5450   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
M  END

ASE
  Mrv1652305271900222D          

 16 17  0  0  0  0            999 V2000
   -2.1330    0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3261    0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -0.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6232   -0.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4037   -1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107   -1.3613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    0.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260    0.0432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5404   -0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2549    0.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5404   -1.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001238

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCC1=CNC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)

> <INCHI_KEY>
MVAWJSIDNICKHF-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.2518

> <EXACT_MASS>
218.105527702

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.59486306036732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.0017187313333336

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.20389827867616

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.556518591797836

> <JCHEM_PKA_STRONGEST_BASIC>
-1.568855406202275

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
61.7976

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylserotonin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001238
     RDKit          3D
N-Acetylserotonin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -5.1424    0.4211   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    0.4261   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363    0.3325    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    0.5300   -1.0283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5282   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094   -0.7309   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.0039    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -2.2301    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1132   -2.2413    1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.0785    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -0.6029    0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791    0.6618    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.4468   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    2.7273   -0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014    0.9417   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335   -0.3001    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3794    0.7011   -1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6841    1.0815    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5978   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868    0.6095   -2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.4204   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.7046   -1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -0.9281    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203   -1.5637   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -3.0839    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424   -3.0572    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913   -1.2583    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028    1.0588    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3598    3.5405   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309    1.5450   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ASE                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.982   1.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.475   1.402   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.999  -0.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.012   0.577   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.536  -0.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.030  -1.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.593  -0.689   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.754  -2.221   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.260  -2.541   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -4.458   3.186   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.741   0.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.075  -0.689   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.409   0.081   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.742  -0.689   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.076   0.081   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.742  -2.229   0.000  0.00  0.00           O+0
CONECT    1    2    4   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    6    7                                                  
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    3    5    9                                                  
CONECT    7    3    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10    1                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0001238
HETATM    1  C1  UNL     1      -5.142   0.421  -0.299  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.681   0.426  -0.015  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.336   0.333   1.185  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.702   0.530  -1.028  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.277   0.528  -0.757  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.909  -0.731  -0.146  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.472  -1.004   0.230  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.811  -2.230   0.790  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.113  -2.241   1.045  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.645  -1.079   0.677  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.936  -0.603   0.733  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.179   0.662   0.269  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.182   1.447  -0.239  1.00  0.00           C  
HETATM   14  O2  UNL     1       3.418   2.727  -0.711  1.00  0.00           O  
HETATM   15  C11 UNL     1       1.901   0.942  -0.281  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.633  -0.300   0.168  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.379   0.701  -1.332  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.684   1.082   0.425  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.583  -0.598  -0.129  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.087   0.610  -2.007  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.157   1.420  -0.080  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.793   0.705  -1.756  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.529  -0.928   0.751  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.220  -1.564  -0.852  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.160  -3.084   1.010  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.642  -3.057   1.475  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.691  -1.258   1.143  1.00  0.00           H  
HETATM   28  H12 UNL     1       5.203   1.059   0.306  1.00  0.00           H  
HETATM   29  H13 UNL     1       3.360   3.541  -0.113  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.131   1.545  -0.672  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    8   16
CONECT    8    9   25
CONECT    9   10   26
CONECT   10   11   11   16
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   15
CONECT   14   29
CONECT   15   16   16   30
END

HMDB0001238
     RDKit          3D
N-Acetylserotonin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -5.1424    0.4211   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    0.4261   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363    0.3325    1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    0.5300   -1.0283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5282   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094   -0.7309   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.0039    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -2.2301    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1132   -2.2413    1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.0785    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -0.6029    0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791    0.6618    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.4468   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    2.7273   -0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014    0.9417   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335   -0.3001    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3794    0.7011   -1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6841    1.0815    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5978   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868    0.6095   -2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.4204   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    0.7046   -1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -0.9281    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203   -1.5637   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -3.0839    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424   -3.0572    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913   -1.2583    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028    1.0588    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3598    3.5405   -0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309    1.5450   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamide	ChEBI
N-Acetyl-5-hydroxytryptamine	ChEBI
5-Hydroxy-N-acetyltryptamine	HMDB
5-Hydroxymelatonin	HMDB
ASE	HMDB
Desmethylmelatonin	HMDB
O-Demethylmelatonin	HMDB
N-Acetylhydroxytryptamine	HMDB

Chemical Formula

C₁₂H₁₄N₂O₂

Average Molecular Weight

218.2518

Monoisotopic Molecular Weight

218.105527702

IUPAC Name

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide

Traditional Name

N-acetylserotonin

CAS Registry Number

1210-83-9

SMILES

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

InChI Identifier

InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)

InChI Key

MVAWJSIDNICKHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboximidic acid
Carboximidic acid derivative
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:17697 )
hydroxyindoles (CHEBI:17697 )
a small molecule (N-ACETYL-SEROTONIN )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19401681)

Organ

Liver (HMDB: HMDB0001238)
Kidney (HMDB: HMDB0001238)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)
Feces (PMID: 29808030)

Cellular substructure

Membrane (HMDB: HMDB0001238)
Cytoplasm (HMDB: HMDB0001238)

Source

Exogenous

Exogenous (HMDB: HMDB0001238)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0001238)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	148.655	30932474
[M+H]+	MetCCS_train_pos	149.845	30932474
[M-H]-	Not Available	150.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000336
[M+H]+	Not Available	150.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000336

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.8 m³·mol⁻¹	ChemAxon
Polarizability	23.59 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]+	149.028	31661259
DarkChem	[M-H]-	148.851	31661259
AllCCS	[M+H]+	149.005	32859911
AllCCS	[M-H]-	152.215	32859911
DeepCCS	[M+H]+	147.323	30932474
DeepCCS	[M-H]-	144.965	30932474
DeepCCS	[M-2H]-	179.852	30932474
DeepCCS	[M+Na]+	154.725	30932474
AllCCS	[M+H]+	149.0	32859911
AllCCS	[M+H-H2O]+	145.0	32859911
AllCCS	[M+NH4]+	152.7	32859911
AllCCS	[M+Na]+	153.8	32859911
AllCCS	[M-H]-	152.2	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	152.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.89 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8272 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1344.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	105.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	157.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	326.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	278.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	110.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	652.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	307.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1125.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	221.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	103.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylserotonin	CC(=O)NCCC1=CNC2=C1C=C(O)C=C2	3722.9	Standard polar	33892256
N-Acetylserotonin	CC(=O)NCCC1=CNC2=C1C=C(O)C=C2	2510.7	Standard non polar	33892256
N-Acetylserotonin	CC(=O)NCCC1=CNC2=C1C=C(O)C=C2	2508.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylserotonin,1TMS,isomer #1	CC(=O)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2464.3	Semi standard non polar	33892256
N-Acetylserotonin,1TMS,isomer #2	CC(=O)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C	2409.8	Semi standard non polar	33892256
N-Acetylserotonin,1TMS,isomer #3	CC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2460.8	Semi standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2382.2	Semi standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2546.1	Standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2673.7	Standard polar	33892256
N-Acetylserotonin,2TMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2477.2	Semi standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2408.7	Standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2680.6	Standard polar	33892256
N-Acetylserotonin,2TMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2437.6	Semi standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2638.8	Standard non polar	33892256
N-Acetylserotonin,2TMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2704.3	Standard polar	33892256
N-Acetylserotonin,3TMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2437.7	Semi standard non polar	33892256
N-Acetylserotonin,3TMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2546.0	Standard non polar	33892256
N-Acetylserotonin,3TMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2516.0	Standard polar	33892256
N-Acetylserotonin,1TBDMS,isomer #1	CC(=O)NCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2739.4	Semi standard non polar	33892256
N-Acetylserotonin,1TBDMS,isomer #2	CC(=O)N(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2653.9	Semi standard non polar	33892256
N-Acetylserotonin,1TBDMS,isomer #3	CC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2713.7	Semi standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2877.9	Semi standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2973.6	Standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #1	CC(=O)N(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2848.1	Standard polar	33892256
N-Acetylserotonin,2TBDMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2975.2	Semi standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2851.8	Standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #2	CC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2829.7	Standard polar	33892256
N-Acetylserotonin,2TBDMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2876.5	Semi standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	3030.6	Standard non polar	33892256
N-Acetylserotonin,2TBDMS,isomer #3	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2832.5	Standard polar	33892256
N-Acetylserotonin,3TBDMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3097.3	Semi standard non polar	33892256
N-Acetylserotonin,3TBDMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3146.0	Standard non polar	33892256
N-Acetylserotonin,3TBDMS,isomer #1	CC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2809.5	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.0054 uM	Adult (>18 years old)	Both	Normal	19401681	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.011 uM	Adult (>18 years old)	Both	Schizophrenia	19401681	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Yao JK, Dougherty GG Jr, Reddy RD, Keshavan MS, Montrose DM, Matson WR, Rozen S, Krishnan RR, McEvoy J, Kaddurah-Daouk R: Altered interactions of tryptophan metabolites in first-episode neuroleptic-naive patients with schizophrenia. Mol Psychiatry. 2010 Sep;15(9):938-53. doi: 10.1038/mp.2009.33. Epub 2009 Apr 28. [PubMed:19401681 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

DB04275

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031021

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17697

Food Biomarker Ontology

Not Available

VMH ID

NACSERTN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Balemans M G; Mans D; Smith I; Van Benthem J The influence of GABA on the synthesis of N-acetylserotonin, melatonin, O-acetyl-5-hydroxytryptophol and O-acetyl-5-methoxytryptophol in the pineal gland of the male Wistar rat. Reproduction, nutrition, development (1983), 23(1), 151-60.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
Harumi T, Matsushima S: Separation and assay methods for melatonin and its precursors. J Chromatogr B Biomed Sci Appl. 2000 Sep 29;747(1-2):95-110. [PubMed:11103901 ]
Reiter RJ, Tan DX, Cabrera J, D'Arpa D: Melatonin and tryptophan derivatives as free radical scavengers and antioxidants. Adv Exp Med Biol. 1999;467:379-87. [PubMed:10721079 ]
Oxenkrug GF: Antidepressive and antihypertensive effects of MAO-A inhibition: role of N-acetylserotonin. A review. Neurobiology (Bp). 1999;7(2):213-24. [PubMed:10591054 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

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. Acetylserotonin O-methyltransferase

General function:: Involved in O-methyltransferase activity
Specific function:: Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:: ASMT
Uniprot ID:: P46597
Molecular weight:: 41660.34

Reactions

S-Adenosylmethionine + N-Acetylserotonin → S-Adenosylhomocysteine + Melatonin	details

Showing metabocard for N-Acetylserotonin (HMDB0001238)

MOL for HMDB0001238 (N-Acetylserotonin)

3D MOL for HMDB0001238 (N-Acetylserotonin)

3D SDF for HMDB0001238 (N-Acetylserotonin)

3D-SDF for HMDB0001238 (N-Acetylserotonin)

PDB for HMDB0001238 (N-Acetylserotonin)

3D PDB for HMDB0001238 (N-Acetylserotonin)

SMILES for HMDB0001238 (N-Acetylserotonin)

INCHI for HMDB0001238 (N-Acetylserotonin)

Structure for HMDB0001238 (N-Acetylserotonin)

3D Structure for HMDB0001238 (N-Acetylserotonin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions