Record Information
Version1.0
Creation date2011-09-21 00:27:47 UTC
Update date2019-11-26 03:21:08 UTC
Primary IDFDB023304
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Hydroxymelatonin
Description6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Hydroxymelatonin exists in all living organisms, ranging from bacteria to humans. 6-Hydroxymelatonin has been detected, but not quantified in, several different foods, such as chinese cabbages, sweet basils, horseradish tree, roman camomiles, and agaves. This could make 6-hydroxymelatonin a potential biomarker for the consumption of these foods.
CAS Number2208-41-5
Structure
Thumb
Synonyms
SynonymSource
Lopac-H-0627ChEBI
6-OxymelatoninHMDB
6-Hydroxy-N-acetyl-5-methoxytryptamineHMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP0.8ALOGPS
logP0.84ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area74.35 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.26 m³·mol⁻¹ChemAxon
Polarizability26.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H16N2O3
IUPAC nameN-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
InChI IdentifierInChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
InChI KeyOMYMRCXOJJZYKE-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1
Average Molecular Weight248.2777
Monoisotopic Molecular Weight248.116092388
Classification
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
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS6-Hydroxymelatonin, 3 TMS, GC-MS Spectrumsplash10-00di-1659000000-71cdfc5bdcf432c9a84aSpectrum
GC-MS6-Hydroxymelatonin, non-derivatized, GC-MS Spectrumsplash10-00di-1659000000-71cdfc5bdcf432c9a84aSpectrum
Predicted GC-MS6-Hydroxymelatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9670000000-71b021cf86103b186db2Spectrum
Predicted GC-MS6-Hydroxymelatonin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fv-7093000000-311814a60377cf77abd4Spectrum
Predicted GC-MS6-Hydroxymelatonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3900000000-533a23d884233d4fd905Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-533a23d884233d4fd905Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0190000000-fc098aa93958c18074a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0970000000-669a6bd5f7e0091b9ca4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fu-1900000000-ffc8f8f8477bce088493Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-b17e668c7f1e41db8d30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3490000000-92983db3c1d0bece458cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-3ac4e7417916c5b2e2f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0920000000-7ed799d3e8693bde62e7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0910000000-eb01005068ed6043a454Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-0900000000-2d6ad727babdb3e4bb6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dff205e638af0877604bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9200000000-d8c0a556f4b94d832017Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r5-4940000000-23e212544ac34c9c55d6Spectrum
NMRNot Available
ChemSpider ID1794
ChEMBL IDCHEMBL127421
KEGG Compound IDC05643
Pubchem Compound ID1864
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04081
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46185
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference