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Record Information
Version4.0
Creation Date2013-07-04 19:02:29 UTC
Update Date2017-10-23 19:15:48 UTC
HMDB IDHMDB0060833
Secondary Accession Numbers
  • HMDB60833
Metabolite Identification
Common NameN-Acetylserotonin glucuronide
DescriptionN-Acetylserotonin glucuronide is a metabolite of melatonin. Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H22N2O8
Average Molecular Weight394.3759
Monoisotopic Molecular Weight394.13761569
IUPAC Name6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-{[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NCCC1=CNC2=C1C=C(OC1OC(C(O)C(O)C1O)C(O)=O)C=C2
InChI Identifier
InChI=1S/C18H22N2O8/c1-8(21)19-5-4-9-7-20-12-3-2-10(6-11(9)12)27-18-15(24)13(22)14(23)16(28-18)17(25)26/h2-3,6-7,13-16,18,20,22-24H,4-5H2,1H3,(H,19,21)(H,25,26)
InChI KeyDRKQFNYKSNWOTC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • N-acetyl-2-arylethylamine
  • O-glycosyl compound
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.89 g/LALOGPS
logP-0.15ALOGPS
logP-0.95ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area161.34 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.81 m³·mol⁻¹ChemAxon
Polarizability38.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9065000000-6bfe6a15b0c7367847bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-5011039000-656e098bf37022f506a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fvs-0259000000-0b61cb9d1692a3d3f8bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0932000000-2784adaaece702197800View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01tc-2910000000-8d611bf7824e228a9b7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kg-1249000000-289b93c478ed0e26ce4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6898000000-4c7fbd985c4a65dba672View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9240000000-7d721a9abf186e9d7a09View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00925
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDCPD-12016
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available