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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 UTC
HMDB IDHMDB0001389
Secondary Accession Numbers
  • HMDB01389
Metabolite Identification
Common NameMelatonin
DescriptionMelatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and. lowering the body temperature. Melatonin is also implicated in the regulation of mood,learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders(ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits. were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.
Structure
Data?1582752197
Synonyms
ValueSource
5-Methoxy-N-acetyltryptamineChEBI
MelatonineChEBI
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamideChEBI
N-Acetyl-5-methoxytryptamineChEBI
MelatoninaKegg
CircadinHMDB
MelatolHMDB
Melatonin (synth.) standard-gradeHMDB
Melatonin (synth.) ultra-pureHMDB
MelovineHMDB
MT6HMDB
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamideHMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamideHMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamideHMDB
N-Acetyl-5-methoxy-tryptamineHMDB
N-Acetyl-5-methoxy-tryptamine melatonineHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamideHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-acetamideHMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamideHMDB
N-[2-(5-Methoxyindol-3-yl)ethyl]-acetamideHMDB
RegulinHMDB
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamideHMDB
{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamideHMDB
3-(2-Acetamidoethyl)-5-methoxyindoleHMDB
MelatoninHMDB
Chemical FormulaC13H16N2O2
Average Molecular Weight232.2783
Monoisotopic Molecular Weight232.121177766
IUPAC NameN-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional Namemelatonin
CAS Registry Number73-31-4
SMILES
COC1=CC2=C(NC=C2CCNC(C)=O)C=C1
InChI Identifier
InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
InChI KeyDRLFMBDRBRZALE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Anisole
  • Alkyl aryl ether
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg153.53430932474
[M+H]+CBM153.430932474
[M+H]+MetCCS_train_pos154.33130932474
[M-H]-Not Available155.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000337
[M+H]+Not Available154.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000337
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.42ALOGPS
logP1.15ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.28 m³·mol⁻¹ChemAxon
Polarizability25.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.9231661259
DarkChem[M-H]-154.28731661259
AllCCS[M+H]+153.24932859911
AllCCS[M-H]-157.77532859911
DeepCCS[M+H]+154.28330932474
DeepCCS[M-H]-151.92530932474
DeepCCS[M-2H]-184.93330932474
DeepCCS[M+Na]+160.37630932474
AllCCS[M+H]+153.232859911
AllCCS[M+H-H2O]+149.432859911
AllCCS[M+NH4]+156.832859911
AllCCS[M+Na]+157.932859911
AllCCS[M-H]-157.832859911
AllCCS[M+Na-2H]-157.932859911
AllCCS[M+HCOO]-158.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MelatoninCOC1=CC2=C(NC=C2CCNC(C)=O)C=C13493.8Standard polar33892256
MelatoninCOC1=CC2=C(NC=C2CCNC(C)=O)C=C12388.8Standard non polar33892256
MelatoninCOC1=CC2=C(NC=C2CCNC(C)=O)C=C12436.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Melatonin,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C2455.1Semi standard non polar33892256
Melatonin,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C2391.9Standard non polar33892256
Melatonin,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C2942.9Standard polar33892256
Melatonin,1TMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C12337.0Semi standard non polar33892256
Melatonin,1TMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C12493.9Standard non polar33892256
Melatonin,1TMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C12961.8Standard polar33892256
Melatonin,2TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C2377.2Semi standard non polar33892256
Melatonin,2TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C2552.5Standard non polar33892256
Melatonin,2TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C2692.7Standard polar33892256
Melatonin,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C2675.3Semi standard non polar33892256
Melatonin,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C2586.8Standard non polar33892256
Melatonin,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C2999.0Standard polar33892256
Melatonin,1TBDMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C12585.8Semi standard non polar33892256
Melatonin,1TBDMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C12690.6Standard non polar33892256
Melatonin,1TBDMS,isomer #2COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C13015.2Standard polar33892256
Melatonin,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2803.8Semi standard non polar33892256
Melatonin,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2933.3Standard non polar33892256
Melatonin,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2857.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0490000000-aa93967315af900a76ce2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03k9-0900000000-a15ee6def3f8d75b12312014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0490000000-94ef1be9ab930060778a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-MS (2 TMS)splash10-001i-1490000000-03e24298c7bd1ed4066a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-MS (Non-derivatized)splash10-001i-1490000000-03e24298c7bd1ed4066a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)splash10-001j-0590000000-63d5e32dd5f7877a44022017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)splash10-001i-0590000000-52b3a733f8b49582d3fb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)splash10-0229-1900000000-d81c6f617bc4860661362017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-4920000000-a8d9d614e9f8769a13592017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03k9-1900000000-45ee4fdc7acdb33dad3b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0159-0090000000-939a1caf5760c0ba189c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0006-0930000000-9e6fcea2c634ac9d85a02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-0900000000-ddd29e731a7de56c18082012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-0900000000-34b4fb52810a15ea5bd62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-001i-0090000000-5ca2df63ec2baefdae8c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOFsplash10-0159-0090000000-939a1caf5760c0ba189c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOFsplash10-0006-0930000000-9e6fcea2c634ac9d85a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-ddd29e731a7de56c18082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-34b4fb52810a15ea5bd62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOFsplash10-001i-0090000000-5ca2df63ec2baefdae8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QTOF , negative-QTOFsplash10-00lr-0090000000-3c42f6997539afb446822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QTOF , negative-QTOFsplash10-014m-0960000000-7991e64dacb3c7f5cf322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-882be43bc196e928a3cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin , negative-QTOFsplash10-014i-0190000000-ddda9232f0e8e1b402f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 60V, Negative-QTOFsplash10-0006-0900000000-24977ebbbf8d806331422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 10V, Negative-QTOFsplash10-02u0-0960000000-a53f0bcd21c20cd44cfa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 35V, Negative-QTOFsplash10-00kf-0950000000-58b73ecf5d765d8f6c012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 15V, Negative-QTOFsplash10-0159-0090000000-de8a238bc05d176027cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 20V, Negative-QTOFsplash10-00kf-0910000000-9996bcba8fb3d61347d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 75V, Negative-QTOFsplash10-0006-0900000000-a290024caadd7d64fe8f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 90V, Negative-QTOFsplash10-0006-0900000000-8be298c9d42d7769f1292021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 40V, Negative-QTOFsplash10-0006-0900000000-a041de616cbb390bca582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 40V, Negative-QTOFsplash10-0006-0900000000-d7ba873af42444fb4b0a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 20V, Negative-QTOFsplash10-00kf-1940000000-9556b19d359c6c0f9d662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Melatonin 35V, Negative-QTOFsplash10-014i-0190000000-6462edd7b08702e1f49e2021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Pineal Gland
  • Placenta
  • Platelet
  • Prostate
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00019 +/- 0.00015 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00006 +/- 0.000015 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.000063 +/- 0.000026 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00256 +/- 0.00168 uMInfant (0-1 year old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.000210 +/- 5.635e-05 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00006 +/- 0.000015 uMNewborn (0-30 days old)MaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0279 (0.00-0.0558) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.191 +/- 0.201 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.0000033 (0.0000006-0.000006) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00140 +/- 0.00103 uMAdult (>18 years old)Both
Uremia
details
UrineDetected and Quantified0.00210 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Associated OMIM IDsNone
DrugBank IDDB01065
Phenol Explorer Compound IDNot Available
FooDB IDFDB004234
KNApSAcK IDNot Available
Chemspider ID872
KEGG Compound IDC01598
BioCyc IDN-ACETYL-5-METHOXY-TRYPTAMINE
BiGG ID37965
Wikipedia LinkMelatonin
METLIN ID73
PubChem Compound896
PDB IDNot Available
ChEBI ID16796
Food Biomarker OntologyNot Available
VMH IDMELATN
MarkerDB IDMDB00000319
Good Scents IDNot Available
References
Synthesis ReferenceHelmut M. Hügel and Faizul Nurlawis. Short synthesis of melatonin. Heterocycles (2003), Vol. 60, No. 10, pp. 2349 - 2354.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Slominski A, Pisarchik A, Zbytek B, Tobin DJ, Kauser S, Wortsman J: Functional activity of serotoninergic and melatoninergic systems expressed in the skin. J Cell Physiol. 2003 Jul;196(1):144-53. [PubMed:12767050 ]
  2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [PubMed:15992934 ]
  3. Christofides J, Bridel M, Egerton M, Mackay GM, Forrest CM, Stoy N, Darlington LG, Stone TW: Blood 5-hydroxytryptamine, 5-hydroxyindoleacetic acid and melatonin levels in patients with either Huntington's disease or chronic brain injury. J Neurochem. 2006 May;97(4):1078-88. Epub 2006 Mar 29. [PubMed:16573644 ]
  4. Drake MJ, Mills IW, Noble JG: Melatonin pharmacotherapy for nocturia in men with benign prostatic enlargement. J Urol. 2004 Mar;171(3):1199-202. [PubMed:14767300 ]
  5. Lahiri DK, Chen D, Lahiri P, Rogers JT, Greig NH, Bondy S: Melatonin, metals, and gene expression: implications in aging and neurodegenerative disorders. Ann N Y Acad Sci. 2004 Dec;1035:216-30. [PubMed:15681810 ]
  6. Bangha E, Lauth D, Kistler GS, Elsner P: Daytime serum levels of melatonin after topical application onto the human skin. Skin Pharmacol. 1997;10(5-6):298-302. [PubMed:9449169 ]
  7. Bubenik GA: Localization, physiological significance and possible clinical implication of gastrointestinal melatonin. Biol Signals Recept. 2001 Nov-Dec;10(6):350-66. [PubMed:11721091 ]
  8. Abdel-Wahhab MA, Abdel-Galil MM, El-Lithey M: Melatonin counteracts oxidative stress in rats fed an ochratoxin A contaminated diet. J Pineal Res. 2005 Mar;38(2):130-5. [PubMed:15683468 ]
  9. Chen HM, Hsu JT, Chen JC, Ng CJ, Chiu DF, Chen MF: Delayed neutrophil apoptosis attenuated by melatonin in human acute pancreatitis. Pancreas. 2005 Nov;31(4):360-4. [PubMed:16258371 ]
  10. Fabis M, Pruszynska E, Mackowiak P: In vivo and in situ action of melatonin on insulin secretion and some metabolic implications in the rat. Pancreas. 2002 Aug;25(2):166-9. [PubMed:12142740 ]
  11. Messner M, Huether G, Lorf T, Ramadori G, Schworer H: Presence of melatonin in the human hepatobiliary-gastrointestinal tract. Life Sci. 2001 Jun 22;69(5):543-51. [PubMed:11510949 ]
  12. Nishida S: Metabolic effects of melatonin on oxidative stress and diabetes mellitus. Endocrine. 2005 Jul;27(2):131-6. [PubMed:16217126 ]
  13. Peschke E, Frese T, Chankiewitz E, Peschke D, Preiss U, Schneyer U, Spessert R, Muhlbauer E: Diabetic Goto Kakizaki rats as well as type 2 diabetic patients show a decreased diurnal serum melatonin level and an increased pancreatic melatonin-receptor status. J Pineal Res. 2006 Mar;40(2):135-43. [PubMed:16441550 ]
  14. Reiter RJ, Sainz RM, Lopez-Burillo S, Mayo JC, Manchester LC, Tan DX: Melatonin ameliorates neurologic damage and neurophysiologic deficits in experimental models of stroke. Ann N Y Acad Sci. 2003 May;993:35-47; discussion 48-53. [PubMed:12853293 ]
  15. Okatani Y, Wakatsuki A, Shinohara K, Kaneda C, Fukaya T: Melatonin stimulates glutathione peroxidase activity in human chorion. J Pineal Res. 2001 May;30(4):199-205. [PubMed:11339508 ]
  16. Bubenik GA: Gastrointestinal melatonin: localization, function, and clinical relevance. Dig Dis Sci. 2002 Oct;47(10):2336-48. [PubMed:12395907 ]
  17. Wurtman RJ, Ozaki Y: Physiological control of melatonin synthesis and secretion: mechanisms, generating rhythms in melatonin, methoxytryptophol, and arginine vasotocin levels and effects on the pineal of endogenous catecholamines, the estrous cycle, and environmental lighting. J Neural Transm Suppl. 1978;(13):59-70. [PubMed:288858 ]
  18. Kobayashi H, Kromminga A, Dunlop TW, Tychsen B, Conrad F, Suzuki N, Memezawa A, Bettermann A, Aiba S, Carlberg C, Paus R: A role of melatonin in neuroectodermal-mesodermal interactions: the hair follicle synthesizes melatonin and expresses functional melatonin receptors. FASEB J. 2005 Oct;19(12):1710-2. Epub 2005 Jul 19. [PubMed:16030176 ]
  19. Johe PD, Osterud B: The in vivo effect of melatonin on cellular activation processes in human blood during strenuous physical exercise. J Pineal Res. 2005 Oct;39(3):324-30. [PubMed:16150115 ]
  20. Paakkonen T, Makinen TM, Leppaluoto J, Vakkuri O, Rintamaki H, Palinkas LA, Hassi J: Urinary melatonin: a noninvasive method to follow human pineal function as studied in three experimental conditions. J Pineal Res. 2006 Mar;40(2):110-5. [PubMed:16441547 ]
  21. Atkinson G, Holder A, Robertson C, Gant N, Drust B, Reilly T, Waterhouse J: Effects of melatonin on the thermoregulatory responses to intermittent exercise. J Pineal Res. 2005 Nov;39(4):353-9. [PubMed:16207290 ]
  22. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [PubMed:7773197 ]
  23. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [PubMed:11462772 ]
  24. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [PubMed:15206778 ]
  25. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [PubMed:16217125 ]
  26. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. [PubMed:18187545 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Reactions
S-Adenosylmethionine + N-Acetylserotonin → S-Adenosylhomocysteine + Melatonindetails
References
  1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [PubMed:180879 ]
General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular weight:
25918.4
References
  1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [PubMed:19463840 ]
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [PubMed:15636586 ]
  2. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. [PubMed:18237195 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5
References
  1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. [PubMed:18516076 ]
General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails
References
  1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [PubMed:15636586 ]
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
References
  1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]
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
References
  1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. [PubMed:17003850 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
References
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [PubMed:15626586 ]

Only showing the first 10 proteins. There are 18 proteins in total.