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Human Metabolome Database Version 3.5

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Showing metabocard for Melatonin (HMDB01389)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:27 -0700
HMDB ID HMDB01389
Secondary Accession Numbers None
Metabolite Identification
Common Name Melatonin
Description Melatonin 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5-Methoxy-N-acetyltryptamine
  2. Circadin
  3. Melatol
  4. Melatonin
  5. Melatonin (synth.) standard-grade
  6. Melatonin (synth.) ultra-pure
  7. Melatonine
  8. Melovine
  9. MT6
  10. N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
  11. N-(2-(5-Methoxyindol-3-yl)ethyl)-Acetamide
  12. N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide
  13. N-Acetyl-5-methoxy-tryptamine
  14. N-Acetyl-5-methoxy-tryptamine Melatonine
  15. N-Acetyl-5-methoxytryptamine
  16. N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide
  17. N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-Acetamide
  18. N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
  19. N-[2-(5-Methoxyindol-3-yl)ethyl]-Acetamide
  20. N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide
  21. Regulin
  22. {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} Acetamide
  23. {N-[2-(5-methoxyindol-3-yl)ethyl]-} Acetamide
Chemical Formula C13H16N2O2
Average Molecular Weight 232.2783
Monoisotopic Molecular Weight 232.121177766
IUPAC Name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional IUPAC Name melatonin
CAS Registry Number 73-31-4
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 Key DRLFMBDRBRZALE-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Tryptamines and Derivatives
Other Descriptors
  • Indole alkaloids(KEGG)
  • Indoles
  • Melatonin(KEGG)
  • Tryptamines and Derivatives
  • a small molecule(Cyc)
  • acetamides(ChEBI)
  • tryptamines(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Carboxamide Group
  • Pyrrole
  • Secondary Carboxylic Acid Amide
Direct Parent Serotonins
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tryptophan metabolism
  • Electron donor
  • Enzyme co-factor
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 117 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.14 g/L ALOGPS
LogP 1.42 ALOGPS
LogP 1.15 ChemAxon
LogS -3.21 ALOGPS
pKa (strongest acidic) 15.8 ChemAxon
pKa (strongest basic) -0.94 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 54.12 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 66.28 ChemAxon
Polarizability 25.49 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Liver
  • Brain
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Gonads
  • Gut
  • Ovary
  • Neutrophil
  • Gastrointestinal Tract
  • Skeletal
  • Pineal Gland
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.00019 +/- 0.00015 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.00006 +/- 0.000015 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.000063 +/- 0.000026 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
0.00256 +/- 0.00168 uM Infant (0-1 year old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
0.00006 +/- 0.000015 uM Newborn (0-30 days old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0279 (0.00-0.0558) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.0000033 (0.0000006-0.000006) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01065 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB004234
KNApSAcK ID Not Available
Chemspider ID 872 Link_out
KEGG Compound ID C01598 Link_out
BioCyc ID N-ACETYL-5-METHOXY-TRYPTAMINE Link_out
BiGG ID 37965 Link_out
Wikipedia Link Melatonin Link_out
NuGOwiki Link HMDB01389 Link_out
Metagene Link HMDB01389 Link_out
METLIN ID 73 Link_out
PubChem Compound 896 Link_out
PDB ID ML1 Link_out
ChEBI ID 16796 Link_out
References
Synthesis Reference Reddy, Gaddam Om; Sarma, Mamillapilli Ramabhadra; Prabhakar, Chebiyyam. An improved process for the preparation of melatonin. Indian (2001), 30 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. Bubenik GA: Localization, physiological significance and possible clinical implication of gastrointestinal melatonin. Biol Signals Recept. 2001 Nov-Dec;10(6):350-66. Pubmed: 11721091 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. Nishida S: Metabolic effects of melatonin on oxidative stress and diabetes mellitus. Endocrine. 2005 Jul;27(2):131-6. Pubmed: 16217126 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. Bubenik GA: Gastrointestinal melatonin: localization, function, and clinical relevance. Dig Dis Sci. 2002 Oct;47(10):2336-48. Pubmed: 12395907 Link_out
  16. 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 Link_out
  17. 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 Link_out
  18. 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 Link_out
  19. 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 Link_out
  20. 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 Link_out
Enzymes
Name: Hydroxyindole O-methyltransferase
Reactions:
  • S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin [RN:R03130]
Gene Name: ASMT
Uniprot ID: P46597 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribosyldihydronicotinamide dehydrogenase [quinone]
Reactions:
  • 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone = 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone [RN:R07361]
Gene Name: NQO2
Uniprot ID: P16083 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Myeloperoxidase
Reactions:
  • donor + H2O2 = oxidized donor + 2 H2O [RN:R03532]
Gene Name: MPO
Uniprot ID: P05164 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil peroxidase
Reactions:
  • donor + H2O2 = oxidized donor + 2 H2O [RN:R03532]
Gene Name: EPX
Uniprot ID: P11678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Indoleamine 2,3-dioxygenase 1
Reactions:
  • (1) D-tryptophan + O2 = N-formyl-D-kynurenine [RN:R07362]
  • (2) L-tryptophan + O2 = N-formyl-L-kynurenine [RN:R00678]
Gene Name: IDO1
Uniprot ID: P14902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calmodulin
Reactions:
    Gene Name: CALM1
    Uniprot ID: P62158 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Estrogen receptor
    Reactions:
      Gene Name: ESR1
      Uniprot ID: P03372 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Calreticulin
      Reactions:
        Gene Name: CALR
        Uniprot ID: P27797 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Melatonin receptor type 1A
        Reactions:
          Gene Name: MTNR1A
          Uniprot ID: P48039 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Melatonin receptor type 1B
          Reactions:
            Gene Name: MTNR1B
            Uniprot ID: P49286 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Nuclear receptor ROR-beta
            Reactions:
              Gene Name: RORB
              Uniprot ID: Q92753 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA