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
StatusDetected and Quantified
Creation Date2006-08-13 10:28:32 UTC
Update Date2018-05-20 20:24:57 UTC
HMDB IDHMDB0004081
Secondary Accession Numbers
  • HMDB04081
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 considered to be a practically insoluble (in water) and relatively neutral molecule. 6-Hydroxymelatonin has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 6-hydroxymelatonin is primarily located in the cytoplasm. 6-Hydroxymelatonin can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 1A1. In humans, 6-hydroxymelatonin is involved in the tryptophan metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
Lopac-H-0627ChEBI
6-OxymelatoninMeSH
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
DescriptionThis compound 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:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 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
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Adrenal Medulla
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00024 (0.00008-0.0004) uMAdult (>18 years old)BothNormal 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
    Phenol Explorer Compound IDNot Available
    FoodDB 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)Download (PDF)
    General References
    1. 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. [PubMed:3035087 ]
    2. 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. [PubMed:3608151 ]
    3. 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. [PubMed:7562371 ]
    4. 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. [PubMed:3436070 ]
    5. 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. [PubMed:2005207 ]
    6. 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. [PubMed:3829375 ]
    7. 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. [PubMed:11452239 ]

    Only showing the first 10 proteins. There are 24 proteins in total.

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    General function:
    Involved in monooxygenase activity
    Specific function:
    Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
    Gene Name:
    CYP2C19
    Uniprot ID:
    P33261
    Molecular weight:
    55944.565
    General function:
    Involved in monooxygenase activity
    Specific function:
    Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
    Gene Name:
    CYP2E1
    Uniprot ID:
    P05181
    Molecular weight:
    56848.42
    General function:
    Involved in monooxygenase activity
    Specific function:
    Exhibits low testosterone 6-beta-hydroxylase activity.
    Gene Name:
    CYP3A43
    Uniprot ID:
    Q9HB55
    Molecular weight:
    57756.285
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
    Gene Name:
    CYP1B1
    Uniprot ID:
    Q16678
    Molecular weight:
    60845.33
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP2C18
    Uniprot ID:
    P33260
    Molecular weight:
    55710.075
    General function:
    Secondary metabolites biosynthesis, transport and catabolism
    Specific function:
    May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
    Gene Name:
    CYP2F1
    Uniprot ID:
    P24903
    Molecular weight:
    55500.64
    General function:
    Involved in monooxygenase activity
    Specific function:
    Not Available
    Gene Name:
    CYP4X1
    Uniprot ID:
    Q8N118
    Molecular weight:
    58874.62
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81

    Only showing the first 10 proteins. There are 24 proteins in total.