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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:19 UTC
NP-MRD IDNP0000673
Secondary Accession NumbersNone
Natural Product 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
Thumb
Synonyms
ValueSource
5-Methoxy-N-acetyltryptamineChEBI
MelatonineChEBI
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamideChEBI
N-Acetyl-5-methoxytryptamineChEBI
MelatoninaKegg
MelatobelKegg
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 Mass232.2783 Da
Monoisotopic Mass232.12118 Da
IUPAC NameN-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
Traditional Namemelatonin
CAS Registry Number73-31-4
SMILES
COC1=CC=C2NC=C(CCNC(C)=O)C2=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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Acetabularia acetabulumKNApSAcK Database
Aloe velaKNApSAcK Database
Andrographis paniculatusKNApSAcK Database
Angelica biserrataKNApSAcK Database
Angelica sinensisKNApSAcK Database
Apium graveolensKNApSAcK Database
Arnebia euchromaKNApSAcK Database
Avena sativaKNApSAcK Database
Beta vulgarisKNApSAcK Database
Brassica nigraKNApSAcK Database
Chenopodium rubrumKNApSAcK Database
Cistanche deseriocolaKNApSAcK Database
Citrus reticulataKNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
Coptis chinensisKNApSAcK Database
Coriandrum sativumKNApSAcK Database
Cucumis sativusKNApSAcK Database
Curcuma aeruginosaKNApSAcK Database
Dendranthema morifoliumKNApSAcK Database
Desmodium styracifoliumKNApSAcK Database
Dunaliella teriolectaKNApSAcK Database
Elettaria cardamomumKNApSAcK Database
Epimedium brevicornumKNApSAcK Database
Eucommia ulmoidesKNApSAcK Database
Festuca arundinaceaKNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Forsythia suspensaKNApSAcK Database
Fragaria x ananassaKNApSAcK Database
Gentiana macrophyllaKNApSAcK Database
Gentiana scabraKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Helianthus annuusKNApSAcK Database
Hypericum perforatumKNApSAcK Database
Isatis indigoticaKNApSAcK Database
Juglans regiaKNApSAcK Database
Laminaria digitataKNApSAcK Database
Leonurus japonicusKNApSAcK Database
Linum usitatissimumKNApSAcK Database
Lobelia chinensisKNApSAcK Database
Lonicera japonicaKNApSAcK Database
Lupinus albusKNApSAcK Database
Lycium barbarumKNApSAcK Database
Medicago sativumKNApSAcK Database
Momordica charantiaKNApSAcK Database
Morus albaKNApSAcK Database
Musa spp.KNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Ophiopogon japonicusKNApSAcK Database
Oryza sativa japonicaKNApSAcK Database
Panax notoginsnegKNApSAcK Database
Papaver somniferumKNApSAcK Database
Patrinia scabiosifoliaKNApSAcK Database
Pharbitis nilKNApSAcK Database
Phellodendron amurenseKNApSAcK Database
Piper nigrumKNApSAcK Database
Polygala tenuifoliaKNApSAcK Database
Polygonatum sibiricumKNApSAcK Database
Polygonum multiflorumKNApSAcK Database
Prunella vulgarisKNApSAcK Database
Prunus amygdalusKNApSAcK Database
Prunus aviumKNApSAcK Database
Prunus cerasusKNApSAcK Database
Pueraria lobataKNApSAcK Database
Punica granatumKNApSAcK Database
Raphanus sativusKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Rheum palmatumKNApSAcK Database
Rubus chingiiKNApSAcK Database
Salvia miltiorrhizaKNApSAcK Database
Scrophularia ningpoensisKNApSAcK Database
Scutellaria amoenaKNApSAcK Database
Scutellaria baicalensisKNApSAcK Database
Senna toraKNApSAcK Database
Sesbania glandifloraKNApSAcK Database
Sesbania sesbanKNApSAcK Database
Silybum marianumKNApSAcK Database
Sinapis albaKNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Sophora flavescensKNApSAcK Database
Syzygium aromaticumKNApSAcK Database
Tanacetum partheniumKNApSAcK Database
Taxillus chinensisKNApSAcK Database
Trigonella foenum-graecumKNApSAcK Database
Uncaria rhynchophyllaKNApSAcK Database
Viola philipicaKNApSAcK Database
Vitis viniferaKNApSAcK Database
Zea maysKNApSAcK Database
Ziziphus jujubaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Alexandrium lusitanicumKNApSAcK Database
Amphidinium carteraeKNApSAcK Database
Bombyx batryticatusKNApSAcK Database
Chondrus crispusKNApSAcK Database
Erythrobacter longusKNApSAcK Database
Euglena gracilisKNApSAcK Database
Gracilaria tenustipitataKNApSAcK Database
Homo sapiensKNApSAcK Database
Neurospora crassaKNApSAcK Database
Palmaria palmataKNApSAcK Database
Porphyra umbilicalisKNApSAcK Database
Rhodospirillum rubrumKNApSAcK Database
Saccharomyces cerevisiaeKNApSAcK Database
Scolopendra subspinipesKNApSAcK Database
Tetrahymena thermophilaKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 °CNot Available
Boiling Point512.83 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1164 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.043 (est)The Good Scents Company Information System
Predicted 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
External Links
HMDB IDHMDB0001389
DrugBank IDDB01065
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004234
KNApSAcK IDC00052006
Chemspider ID872
KEGG Compound IDC01598
BioCyc IDN-ACETYL-5-METHOXY-TRYPTAMINE
BiGG ID37965
Wikipedia LinkMelatonin
METLIN ID73
PubChem Compound896
PDB IDNot Available
ChEBI ID16796
Good Scents IDrw1256771
References
General References
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  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 ]