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Human Metabolome Database Version 2.5

 

Showing metabocard for N-Acetylserotonin (HMDB01238)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:36
Accession Number HMDB01238
Secondary Accession Numbers Not Available
Common Name N-Acetylserotonin
Description 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)
Synonyms
  1. 5-Hydroxy-N-acetyltryptamine
  2. 5-Hydroxymelatonin
  3. ASE
  4. N-Acetyl-5-hydroxytryptamine
  5. N-Acetylserotonin
Chemical IUPAC Name N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]ethanamide
Chemical Formula C12H14N2O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Indoles and Indole Derivatives
Sub Class
  • Indole acids
Family
  • Mammalian Metabolite
Species
  • phenol or hydroxyhetarene
  • secondary carboxylic acid amide
  • aromatic compound
  • heterocyclic compound
Biofunction
  • Component of Tryptophan metabolism
Application
—
Source
  • Endogenous
Average Molecular Weight 218.252
Monoisotopic Molecular Weight 218.105530
Isomeric SMILES CC(=O)NCCC1=CNC2=C1C=C(O)C=C2
Canonical SMILES CC(=O)NCCC1=CNC2=C1C=C(O)C=C2
KEGG Compound ID C00978 Link Image
BioCyc ID N-ACETYL-SEROTONIN Link Image
BiGG ID 36527 Link Image
Wikipedia Link ASE Link Image
NuGOwiki Link HMDB01238 Link Image
Metagene Link HMDB01238 Link Image
METLIN ID 366 Link Image
PubChem Compound 903 Link Image
PubChem Substance 11494183 Link Image
ChEBI ID 17697 Link Image
CAS Registry Number 1210-83-9
InChI Identifier InChI=1/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)
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.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.569 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 0.98 [Predicted by ALOGPS]; 1.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 Link Image map00380 Link Image
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Serotonin N-acetyltransferase
  2. Hydroxyindole O-methyltransferase
Enzyme 1 [top]
Enzyme 1 ID 5259
Enzyme 1 Name Serotonin N-acetyltransferase
Enzyme 1 Synonyms
  1. Aralkylamine N- acetyltransferase
  2. AA-NAT
  3. Serotonin acetylase
Enzyme 1 Gene Name AANAT
Enzyme 1 Protein Sequence >Serotonin N-acetyltransferase 
MSTQSTHPLKPEAPRLPPGIPESPSCQRRHTLPASEFRCLTPEDAVSAFEIEREAFISVL
GVCPLYLDEIRHFLTLCPELSLGWFEEGCLVAFIIGSLWDKERLMQESLTLHRSGGHIAH
LHVLAVHRAFRQQGRGPILLWRYLHHLGSQPAVRRAALMCEDALVPFYERFSFHAVGPCA
ITVGSLTFMELHCSLRGHPFLRRNSGC
Enzyme 1 Number of Residues 207
Enzyme 1 Molecular Weight 23344
Enzyme 1 Theoretical pI 7.57
Enzyme 1 GO Classification
Function
  • N-acetyltransferase activity
  • acetyltransferase activity
  • acyltransferase activity
  • catalytic activity
  • transferase activity
  • transferase activity, transferring acyl groups
  • transferase activity, transferring groups other than amino-acyl groups
Process
—
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Catalyzes the N-acetylation of serotonin into N- acetylserotonin
Enzyme 1 Pathways
Enzyme 1 Reactions
  • acetyl-CoA + an aralkylamine = CoA + an N-acetylaralkylamine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 1389594 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q16613 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name SNAT_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >624 bp 
ATGTCCACGCAGAGCACCCACCCCCTGAAACCTGAGGCCCCACGTCTGCCACCTGGGATC
CCCGAGTCCCCGAGCTGTCAGCGGCGCCACACACTCCCTGCCAGTGAGTTTCGCTGCCTC
ACCCCGGAGGACGCTGTCAGCGCCTTTGAGATCGAGCGTGAAGCCTTCATCTCCGTCTTG
GGCGTCTGCCCCCTGTACCTGGATGAGATCCGGCACTTCCTGACCCTATGTCCAGAGCTG
TCCCTGGGCTGGTTCGAGGAGGGCTGCCTTGTGGCCTTCATCATCGGCTCGCTCTGGGAC
AAGGAGAGACTCATGCAGGAGTCACTGACGCTGCACAGGTCTGGGGGCCACATAGCCCAC
CTGCATGTGCTGGCCGTGCACCGCGCCTTCCGGCAGCAGGGCAGGGGCCCCATCCTGCTG
TGGCGCTACCTGCACCACCTGGGCAGCCAGCCGGCCGTGCGCCGGGCCGCGCTCATGTGC
GAGGACGCGCTGGTACCCTTCTATGAGAGGTTCAGCTTCCACGCCGTGGGCCCCTGCGCC
ATCACCGTGGGCTCCCTCACCTTCATGGAGCTCCACTGCTCCCTGCGGGGCCACCCCTTC
CTGCGCAGGAACAGCGGCTGCTGA
Enzyme 1 GenBank Gene ID U40391 Link Image
Enzyme 1 GeneCard ID AANAT Link Image
Enzyme 1 GenAtlas ID AANAT Link Image
Enzyme 1 HGNC ID HGNC:19 Link Image
Enzyme 1 Chromosome Location 17
Enzyme 1 Locus 17q25
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Coon SL, Mazuruk K, Bernard M, Roseboom PH, Klein DC, Rodriguez IR: The human serotonin N-acetyltransferase (EC 2.3.1.87) gene (AANAT): structure, chromosomal localization, and tissue expression. Genomics. 1996 May 15;34(1):76-84. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 5333
Enzyme 2 Name Hydroxyindole O-methyltransferase
Enzyme 2 Synonyms
  1. HIOMT
  2. Acetylserotonin O-methyltransferase
  3. ASMT
Enzyme 2 Gene Name ASMT
Enzyme 2 Protein Sequence >Hydroxyindole O-methyltransferase 
MGSSEDQAYRLLNDYANGFMVSQVLFAACELGVFDLLAEAPGPLDVAAVAAGVRASAHGT
ELLLDICVSLKLLKVETRGGKAFYRNTELSSDYLTTVSPTSQCSMLKYMGRTSYRCWGHL
ADAVREGRNQYLETFGVPAEELFTAIYRSEGERLQFMQALQEVWSVNGRSVLTAFDLSVF
PLMCDLGGGAGALAKECMSLYPGCKITVFDIPEVVWTAKQHFSFQEEEQIDFQEGDFFKD
PLPEADLYILARVLHDWADGKCSHLLERIYHTCKPGGGILVIESLLDEDRRGPLLTQLYS
LNMLVQTEGQERTPTHYHMLLSSAGFRDFQFKKTGAIYDAILARK
Enzyme 2 Number of Residues 345
Enzyme 2 Molecular Weight 38453
Enzyme 2 Theoretical pI 4.82
Enzyme 2 GO Classification
Function
  • O-methyltransferase activity
  • catalytic activity
  • methyltransferase activity
  • transferase activity
  • transferase activity, transferring one-carbon groups
Process
—
Component
—
Enzyme 2 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 2 Specific Function S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
Enzyme 2 Pathways
Enzyme 2 Reactions
  • S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein Not Available
Enzyme 2 UniProtKB/Swiss-Prot ID P46597 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name HIOM_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID U11098 Link Image
Enzyme 2 GeneCard ID ASMT Link Image
Enzyme 2 GenAtlas ID ASMT Link Image
Enzyme 2 HGNC ID HGNC:750 Link Image
Enzyme 2 Chromosome Location X
Enzyme 2 Locus Xp22.3 or Yp11.3
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Rodriguez IR, Mazuruk K, Schoen TJ, Chader GJ: Structural analysis of the human hydroxyindole-O-methyltransferase gene. Presence of two distinct promoters. J Biol Chem. 1994 Dec 16;269(50):31969-77. [PubMed Link Image]
  2. Donohue SJ, Roseboom PH, Illnerova H, Weller JL, Klein DC: Human hydroxyindole-O-methyltransferase: presence of LINE-1 fragment in a cDNA clone and pineal mRNA. DNA Cell Biol. 1993 Oct;12(8):715-27. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available