Showing metabocard for N-Acetylserotonin (BMDB0001238)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:52 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0001238
Secondary Accession Numbers
  • BMDB01238
Metabolite Identification
Common NameN-Acetylserotonin
DescriptionN-Acetylserotonin, also known as 5-hydroxymelatonin or ASE, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. N-Acetylserotonin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylserotonin exists in all living organisms, ranging from bacteria to humans. N-Acetylserotonin participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylserotonin can be biosynthesized from serotonin and acetyl-CoA; which is mediated by the enzyme serotonin N-acetyltransferase. In addition, N-Acetylserotonin and S-adenosylmethionine can be converted into melatonin and S-adenosylhomocysteine; which is catalyzed by the enzyme acetylserotonin O-methyltransferase. In cattle, N-acetylserotonin is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC12H14N2O2
Average Molecular Weight218.2518
Monoisotopic Molecular Weight218.105527702
IUPAC NameN-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
Traditional NameN-acetylserotonin
CAS Registry Number1210-83-9
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 KeyMVAWJSIDNICKHF-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.
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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f6x-0692000000-96e09fa6d98b96bcf1e4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fsm-0950000000-1bfd0dec31c3cbabefddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udl-0495000000-4408ea40213cdc89bf39View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0690000000-15c09141663fccc3546fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f6x-1592000000-742cca756ead51503626View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0f6x-2695000000-c377bb4d833e7c3880daView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6x-1592000000-742cca756ead51503626View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6x-2695000000-c377bb4d833e7c3880daView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6x-0692000000-60b556c70b30588d69f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6x-0595000000-687eb11cf30796ac9321View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0590000000-3fa8283c51c6d0bcbb54View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0097-5910000000-ceaf51e6bbefe5537258View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9280000000-17099861a602d813f195View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0920000000-9c0d187c13aabfa510d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-025ebd6d665bfe7141d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-1900000000-cdac2a24252af2ce8c65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03yi-2900000000-4fc1ad68abd1d2588527View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0aor-3890000000-f3ae8731ba8f76a62c23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03yi-2900000000-4fc1ad68abd1d2588527View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-73493993faa05c0e2d48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-84ee5e07619ce235bd1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-d1d9419199ca000ac22aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-df6a45ff48d98beeb1feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-66437c0f9179582202ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-4692c1200a9a8c1fa389View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-67746f3e50ff13880beaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-7e71156411b390274e26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-cfd5be5385f370d516f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-a458938615e76563186fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0900000000-84b4aba2486e6b07fb07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-d7a223841dec55cf4d51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-e6590ce23a6fddb5be97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0950000000-524beb3c0eb569b36af4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-a01ac35d32e9651b0b18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qd-1900000000-23a4306d4e9b966e4141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1590000000-6be0bcac0c1150048e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00os-3920000000-16b240b30f4e9fb80a10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-60ab04a4c74a12a09dddView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Kidney
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001238
DrugBank IDDB04275
Phenol Explorer Compound IDNot Available
FooDB IDFDB031021
KNApSAcK IDNot Available
Chemspider ID879
KEGG Compound IDC00978
BioCyc IDN-ACETYL-SEROTONIN
BiGG ID36527
Wikipedia LinkN-acetyl-serotonin
METLIN ID366
PubChem Compound903
PDB IDNot Available
ChEBI ID17697
References
Synthesis ReferenceBalemans 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)Not Available
General References
  1. 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 ]

Enzymes

Enzyme Details
1. Serotonin N-acetyltransferase
General function:
Transcription
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:
O02785
Molecular weight:
22997.0
Reactions
Serotonin + Acetyl-CoA → N-Acetylserotonin + Coenzyme Adetails
Enzyme Details
2. Acetylserotonin O-methyltransferase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine).
Gene Name:
ASMT
Uniprot ID:
P10950
Molecular weight:
37924.0
Reactions
N-Acetylserotonin + S-Adenosylmethionine → Melatonin + S-Adenosylhomocysteinedetails