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Record Information
Version3.6
Creation Date2013-07-22 19:50:11 UTC
Update Date2016-02-11 08:19:02 UTC
HMDB IDHMDB61136
Secondary Accession NumbersNone
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 KeyInChIKey=UEZDFVJSDBULCI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Hydroxyindole
  • Methoxyphenol
  • Indole
  • Resorcinol
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Acetamide
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.24 m3·mol-1ChemAxon
Polarizability27.45 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61136
Metagene LinkHMDB61136
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