6-Hydroxymelatonin (CHEM022526)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:35 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022526
Identification
Common Name6-Hydroxymelatonin
ClassSmall Molecule
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 possibly soluble (in water) and 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 can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 1A1. In cattle, 6-hydroxymelatonin is involved in the metabolic pathway called the tryptophan metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Lopac-H-0627ChEBI
6-OxymelatoninHMDB
6-Hydroxy-N-acetyl-5-methoxytryptamineHMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine HMDB
Chemical FormulaC13H16N2O3
Average Molecular Mass248.278 g/mol
Monoisotopic Mass248.116 g/mol
CAS Registry Number2208-41-5
IUPAC NameN-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional NameN-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
SMILESCOC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1659000000-71cdfc5bdcf432c9a84aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1659000000-71cdfc5bdcf432c9a84aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9670000000-71b021cf86103b186db2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fv-7093000000-311814a60377cf77abd4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3900000000-533a23d884233d4fd905Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-533a23d884233d4fd905Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0190000000-fc098aa93958c18074a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0970000000-669a6bd5f7e0091b9ca4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fu-1900000000-ffc8f8f8477bce088493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-b17e668c7f1e41db8d30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3490000000-92983db3c1d0bece458cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-3ac4e7417916c5b2e2f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0920000000-7ed799d3e8693bde62e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0910000000-eb01005068ed6043a454Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-0900000000-2d6ad727babdb3e4bb6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dff205e638af0877604bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9200000000-d8c0a556f4b94d832017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r5-4940000000-23e212544ac34c9c55d6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004081
FooDB IDFDB023304
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46185
BioCyc IDNot Available
METLIN ID7013
PDB IDNot Available
Wikipedia Link6-Hydroxymelatonin
Chemspider ID1794
ChEBI ID2198
PubChem Compound ID1864
Kegg Compound IDC05643
YMDB IDNot Available
ECMDB IDM2MDB005316
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Karam, Omar; Zunino, Fabien; Chagnaut, Vincent; Jouannetaud, Marie Paule; Jacquesy, Jean Claude. An efficient synthesis of 6-hydroxymelatonin, a human metabolite of melatonin. Tetrahedron Letters (2003), 44(7), 1511-1513.
2. Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103.
3. Bojkowski CJ, Arendt J, Shih MC, Markey SP: Melatonin secretion in humans assessed by measuring its metabolite, 6-sulfatoxymelatonin. Clin Chem. 1987 Aug;33(8):1343-8.
4. Whitson PA, Putcha L, Chen YM, Baker E: Melatonin and cortisol assessment of circadian shifts in astronauts before flight. J Pineal Res. 1995 Apr;18(3):141-7.
5. Nowak R, McMillen IC, Redman J, Short RV: The correlation between serum and salivary melatonin concentrations and urinary 6-hydroxymelatonin sulphate excretion rates: two non-invasive techniques for monitoring human circadian rhythmicity. Clin Endocrinol (Oxf). 1987 Oct;27(4):445-52.
6. Bruce J, Tamarkin L, Riedel C, Markey S, Oldfield E: Sequential cerebrospinal fluid and plasma sampling in humans: 24-hour melatonin measurements in normal subjects and after peripheral sympathectomy. J Clin Endocrinol Metab. 1991 Apr;72(4):819-23.
7. Francis PL, Leone AM, Young IM, Stovell P, Silman RE: Gas chromatographic-mass spectrometric assay for 6-hydroxymelatonin sulfate and 6-hydroxymelatonin glucuronide in urine. Clin Chem. 1987 Apr;33(4):453-7.
8. Hartter S, Ursing C, Morita S, Tybring G, von Bahr C, Christensen M, Rojdmark S, Bertilsson L: Orally given melatonin may serve as a probe drug for cytochrome P450 1A2 activity in vivo: a pilot study. Clin Pharmacol Ther. 2001 Jul;70(1):10-6.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15356035
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16300638
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22430231
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2646423
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=3964785
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=7263843