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Record Information
Version4.0
Creation Date2013-07-04 19:01:01 UTC
Update Date2017-09-27 08:43:55 UTC
HMDB IDHMDB0060812
Secondary Accession Numbers
  • HMDB60812
Metabolite Identification
Common Namecyclic N-Acetylserotonin glucuronide
Descriptioncyclic N-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 FormulaC18H20N2O8
Average Molecular Weight392.36
Monoisotopic Molecular Weight392.121965626
IUPAC Name6-({1-acetyl-1H,2H,3H,8H-pyrrolo[2,3-b]indol-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-({1-acetyl-2H,3H,8H-pyrrolo[2,3-b]indol-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=O)N1CCC2=C1NC1=C2C=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1
InChI Identifier
InChI=1S/C18H20N2O8/c1-7(21)20-5-4-9-10-6-8(2-3-11(10)19-16(9)20)27-18-14(24)12(22)13(23)15(28-18)17(25)26/h2-3,6,12-15,18-19,22-24H,4-5H2,1H3,(H,25,26)
InChI KeyDHEUSGDHJNTOLK-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
  • Pyrroloindole
  • O-glycosyl compound
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Acetamide
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxamide group
  • Polyol
  • Organoheterocyclic compound
  • 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 DescriptorsNot Available
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 Solubility8.37 g/LALOGPS
logP-0.14ALOGPS
logP-0.95ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area152.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity91.68 m³·mol⁻¹ChemAxon
Polarizability38.66 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 IDDBMET00821
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      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