Showing metabocard for Melatonin (BMDB0001389)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:15 UTC
Update Date2020-06-04 18:59:03 UTC
MCDB ID BMDB0001389
Secondary Accession Numbers
  • BMDB01389
Metabolite Identification
Common NameMelatonin
DescriptionMelatonin, also known as circadin or melatol, 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. Melatonin is a drug which is used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. it has received fda orphan drug status as an oral medication for this use. a number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. it appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. it may also improve secondary insomnia associated with various sleep-wake cycle disturbances. other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (dsps), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with il-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. . Melatonin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Melatonin exists in all living organisms, ranging from bacteria to humans. Melatonin participates in a number of enzymatic reactions, within cattle. In particular, Melatonin and S-adenosylhomocysteine can be biosynthesized from N-acetylserotonin and S-adenosylmethionine through the action of the enzyme acetylserotonin O-methyltransferase. In addition, Melatonin can be converted into 6-hydroxymelatonin; which is mediated by the enzyme cytochrome P450 1A1. In cattle, melatonin is involved in the metabolic pathway called the tryptophan metabolism pathway. Melatonin is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0490000000-aa93967315af900a76ce2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03k9-0900000000-a15ee6def3f8d75b12312014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0490000000-94ef1be9ab930060778a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1490000000-03e24298c7bd1ed4066a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1490000000-03e24298c7bd1ed4066a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-0590000000-63d5e32dd5f7877a44022017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0590000000-52b3a733f8b49582d3fb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0229-1900000000-d81c6f617bc4860661362017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-4920000000-a8d9d614e9f8769a13592017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0920000000-f90ec9b77e1a245e35a82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-0900000000-49e4482c65e82ac64b662012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-0900000000-8a4ae0fd610cca992d742012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0159-0090000000-939a1caf5760c0ba189c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0930000000-9e6fcea2c634ac9d85a02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-ddd29e731a7de56c18082012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-34b4fb52810a15ea5bd62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-5ca2df63ec2baefdae8c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0190000000-5bae6e63e9b40e60e0a42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-529bf6d5c2091993f8652012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-158a60fe696120b23b412012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a5c-0900000000-5e86b2de659ce47762c02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-881c0d57239d56c46f2d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0910000000-f256f78adbcbeb2464de2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-bd15d952a2fc6c5cbb232012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-05fr-0900000000-7acf9405f4beeb34566c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-13245183cd8c8cd511c32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-07b3d32f002dba733c102017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0159-0090000000-939a1caf5760c0ba189c2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0950000000-3561167f9cf6abf874652017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-7c590c12649f6abfac962017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-1900000000-6fc07c212072dc15cda12017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1390000000-afe87f80bc60da102bf62017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-3940000000-44812f1a2c7f6216bd232017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-995e110e7943eff538ad2017-07-26View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03k9-1900000000-45ee4fdc7acdb33dad3b2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00003 - 0.00006 uM details
HMDB IDHMDB0001389
DrugBank IDDB01065
Phenol Explorer Compound IDNot Available
FoodDB 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
References
Synthesis ReferenceReddy, 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. Eriksson L, Valtonen M, Laitinen JT, Paananen M, Kaikkonen M: Diurnal rhythm of melatonin in bovine milk: pharmacokinetics of exogenous melatonin in lactating cows and goats. Acta Vet Scand. 1998;39(3):301-10. [PubMed:9787493 ]