Showing metabocard for 6-Hydroxymelatonin (BMDB0004081)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:46 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0004081
Secondary Accession Numbers
  • BMDB04081
Metabolite Identification
Common 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 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.
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 Weight248.2777
Monoisotopic Molecular Weight248.116092388
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
CAS Registry Number2208-41-5
SMILES
COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1659000000-71cdfc5bdcf432c9a84aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1659000000-71cdfc5bdcf432c9a84aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9670000000-71b021cf86103b186db2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fv-7093000000-311814a60377cf77abd4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3900000000-533a23d884233d4fd905View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-533a23d884233d4fd905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0190000000-fc098aa93958c18074a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0970000000-669a6bd5f7e0091b9ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fu-1900000000-ffc8f8f8477bce088493View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-b17e668c7f1e41db8d30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3490000000-92983db3c1d0bece458cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-3ac4e7417916c5b2e2f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0920000000-7ed799d3e8693bde62e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0910000000-eb01005068ed6043a454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-0900000000-2d6ad727babdb3e4bb6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dff205e638af0877604bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9200000000-d8c0a556f4b94d832017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r5-4940000000-23e212544ac34c9c55d6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adrenal Medulla
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004081
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023304
KNApSAcK IDNot Available
Chemspider ID1794
KEGG Compound IDC05643
BioCyc IDNot Available
BiGG ID46185
Wikipedia Link6-Hydroxymelatonin
METLIN ID7013
PubChem Compound1864
PDB IDNot Available
ChEBI ID2198
References
Synthesis ReferenceKaram, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 2U1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the metabolism of arachidonic acid and its conjugates. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase). Acts as an omega and omega-1 hydroxylase for arachidonic acid and possibly for other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes. May downregulate the biological activities of N-arachidonoyl-serotonin, an endocannabinoid that has anti-nociceptive effects through inhibition of fatty acid amide hydrolase FAAH, TRPV1 receptor and T-type calcium channels. Catalyzes C-2 oxidation of the indole ring of N-arachidonoyl-serotonin forming a less active product 2-oxo-N-arachidonoyl-serotonin.
Gene Name:
CYP2U1
Uniprot ID:
Q0IIF9
Molecular weight:
61997.0
Reactions
Melatonin + Oxygen + Reduced flavoprotein → 6-Hydroxymelatonin + Water + Oxidized flavoproteindetails