Record Information
Version1.0
Creation date2011-09-21 00:15:03 UTC
Update date2020-04-21 18:02:43 UTC
Primary IDFDB022505
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetylserotonin
DescriptionN-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) [HMDB]. N-Acetylserotonin is found in many foods, some of which are oregon yampah, barley, ostrich fern, and lovage.
CAS Number1210-83-9
Structure
Thumb
Synonyms
SynonymSource
N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamideChEBI
N-Acetyl-5-hydroxytryptamineChEBI
5-Hydroxy-N-acetyltryptamineHMDB
5-HydroxymelatoninHMDB
ASEHMDB
DesmethylmelatoninHMDB
O-DemethylmelatoninHMDB
N-AcetylhydroxytryptamineHMDB
N-Acetylserotoninhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP0.98ALOGPS
logP1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.12 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.8 m³·mol⁻¹ChemAxon
Polarizability23.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H14N2O2
IUPAC nameN-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
InChI IdentifierInChI=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 KeyMVAWJSIDNICKHF-UHFFFAOYSA-N
Isomeric SMILESCC(=O)NCCC1=CNC2=C1C=C(O)C=C2
Average Molecular Weight218.2518
Monoisotopic Molecular Weight218.105527702
Classification
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0f6x-0692000000-96e09fa6d98b96bcf1e4Spectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0fsm-0950000000-1bfd0dec31c3cbabefddSpectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0udl-0495000000-4408ea40213cdc89bf39Spectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0159-0690000000-15c09141663fccc3546fSpectrum
GC-MSN-Acetylserotonin, 3 TMS, GC-MS Spectrumsplash10-0f6x-1592000000-742cca756ead51503626Spectrum
GC-MSN-Acetylserotonin, 2 TMS, GC-MS Spectrumsplash10-0f6x-2695000000-c377bb4d833e7c3880daSpectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0f6x-1592000000-742cca756ead51503626Spectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0f6x-2695000000-c377bb4d833e7c3880daSpectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0f6x-0692000000-60b556c70b30588d69f4Spectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0f6x-0595000000-687eb11cf30796ac9321Spectrum
GC-MSN-Acetylserotonin, non-derivatized, GC-MS Spectrumsplash10-0159-0590000000-3fa8283c51c6d0bcbb54Spectrum
Predicted GC-MSN-Acetylserotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0097-5910000000-ceaf51e6bbefe5537258Spectrum
Predicted GC-MSN-Acetylserotonin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9280000000-17099861a602d813f195Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0920000000-9c0d187c13aabfa510d9Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-025ebd6d665bfe7141d3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-1900000000-cdac2a24252af2ce8c65Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03yi-2900000000-4fc1ad68abd1d2588527Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0aor-3890000000-f3ae8731ba8f76a62c23Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03yi-2900000000-4fc1ad68abd1d2588527Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-73493993faa05c0e2d48Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0950000000-524beb3c0eb569b36af4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-a01ac35d32e9651b0b18Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qd-1900000000-23a4306d4e9b966e4141Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1590000000-6be0bcac0c1150048e43Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00os-3920000000-16b240b30f4e9fb80a10Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-60ab04a4c74a12a09dddSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID879
ChEMBL IDCHEMBL33103
KEGG Compound IDC00978
Pubchem Compound ID903
Pubchem Substance IDNot Available
ChEBI ID17697
Phenol-Explorer IDNot Available
DrugBank IDDB04275
HMDB IDHMDB01238
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36527
KNApSAcK IDNot Available
HET IDASE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDASE
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Serotonin N-acetyltransferaseAANATQ16613
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference