You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:11 UTC
Update Date2017-12-07 18:56:03 UTC
HMDB IDHMDB0061136
Secondary Accession Numbers
  • HMDB61136
Metabolite Identification
Common Namedi-Hydroxymelatonin
Descriptiondi-Hydroxymelatonin 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 FormulaC13H16N2O4
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
IUPAC NameN-[2-(4,6-dihydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional NameN-[2-(4,6-dihydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=C(NC=C2CCNC(C)=O)C=C1O
InChI Identifier
InChI=1S/C13H16N2O4/c1-7(16)14-4-3-8-6-15-9-5-10(17)13(19-2)12(18)11(8)9/h5-6,15,17-18H,3-4H2,1-2H3,(H,14,16)
InChI KeyUEZDFVJSDBULCI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acetyl-2-arylethylamines. These are compounds containing an acetamide group that is N-linked to an arylethylamine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-acetyl-2-arylethylamines
Alternative Parents
Substituents
  • N-acetyl-2-arylethylamine
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • 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 Solubility0.85 g/LALOGPS
logP0.97ALOGPS
logP0.54ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.58 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.24 m³·mol⁻¹ChemAxon
Polarizability27.45 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-006x-8490000000-bec9bef94acf4d6ad1e9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-4039000000-18c72985eb0fdf0f763cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0090000000-dd1a4276161299ac5e03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1390000000-701a528d340e9f8fe2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-3920000000-cf59fa282b314a84c45fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-957a343ccf028a9a38aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c00-2290000000-ed346d03de7a1eb109dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-e324234c0eeb4cbb22d5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDDBMET00832
      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