NP-MRD: Showing NP-Card for N-Acetylserotonin (NP0000910)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:56 UTC

NP-MRD ID

NP0000910

Secondary Accession Numbers

None

Natural Product 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>
NP0000910

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

218.2518 Da

Monoisotopic Mass

218.10553 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0001238

DrugBank ID

DB04275

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Showing NP-Card for N-Acetylserotonin (NP0000910)

MOL for NP0000910 (N-Acetylserotonin)

3D MOL for NP0000910 (N-Acetylserotonin)

3D SDF for NP0000910 (N-Acetylserotonin)

3D-SDF for NP0000910 (N-Acetylserotonin)

PDB for NP0000910 (N-Acetylserotonin)

3D PDB for NP0000910 (N-Acetylserotonin)

SMILES for NP0000910 (N-Acetylserotonin)

INCHI for NP0000910 (N-Acetylserotonin)

Structure for NP0000910 (N-Acetylserotonin)

3D Structure for NP0000910 (N-Acetylserotonin)