Showing metabocard for Melatonin (BMDB0001389)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
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Record Information
Version1.0
Creation Date2016-09-30 22:45:15 UTC
Update Date2020-06-04 18:59:03 UTC
BMDB IDBMDB0001389
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
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0490000000-aa93967315af900a76ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03k9-0900000000-a15ee6def3f8d75b1231View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0490000000-94ef1be9ab930060778aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1490000000-03e24298c7bd1ed4066aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1490000000-03e24298c7bd1ed4066aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-0590000000-63d5e32dd5f7877a4402View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0590000000-52b3a733f8b49582d3fbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0229-1900000000-d81c6f617bc486066136View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-4920000000-a8d9d614e9f8769a1359View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0920000000-f90ec9b77e1a245e35a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fr-0900000000-49e4482c65e82ac64b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-0900000000-8a4ae0fd610cca992d74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0159-0090000000-939a1caf5760c0ba189cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0930000000-9e6fcea2c634ac9d85a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-ddd29e731a7de56c1808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-34b4fb52810a15ea5bd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0090000000-5ca2df63ec2baefdae8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0190000000-5bae6e63e9b40e60e0a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-529bf6d5c2091993f865View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-158a60fe696120b23b41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a5c-0900000000-5e86b2de659ce47762c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-881c0d57239d56c46f2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0910000000-f256f78adbcbeb2464deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-bd15d952a2fc6c5cbb23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-05fr-0900000000-7acf9405f4beeb34566cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-13245183cd8c8cd511c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-07b3d32f002dba733c10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0159-0090000000-939a1caf5760c0ba189cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0950000000-3561167f9cf6abf87465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-7c590c12649f6abfac96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-1900000000-6fc07c212072dc15cda1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1390000000-afe87f80bc60da102bf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-3940000000-44812f1a2c7f6216bd23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-995e110e7943eff538adView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03k9-1900000000-45ee4fdc7acdb33dad3bView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Milk
  • Neuron
  • Ovary
  • Pancreas
  • Pineal Gland
  • Placenta
  • Platelet
  • Prostate Tissue
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0001389
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
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)Not Available
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 ]

Enzymes

Enzyme Details
1. Cytochrome P450 2U1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the metabolism of arachidonic acid and its conjugates. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase). Acts as an omega and omega-1 hydroxylase for arachidonic acid and possibly for other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes. May downregulate the biological activities of N-arachidonoyl-serotonin, an endocannabinoid that has anti-nociceptive effects through inhibition of fatty acid amide hydrolase FAAH, TRPV1 receptor and T-type calcium channels. Catalyzes C-2 oxidation of the indole ring of N-arachidonoyl-serotonin forming a less active product 2-oxo-N-arachidonoyl-serotonin.
Gene Name:
CYP2U1
Uniprot ID:
Q0IIF9
Molecular weight:
61997.0
Reactions
Melatonin + Oxygen + Reduced flavoprotein → 6-Hydroxymelatonin + Water + Oxidized flavoproteindetails
Enzyme Details
2. Acetylserotonin O-methyltransferase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine).
Gene Name:
ASMT
Uniprot ID:
P10950
Molecular weight:
37924.0
Reactions
N-Acetylserotonin + S-Adenosylmethionine → Melatonin + S-Adenosylhomocysteinedetails
Enzyme Details
3. Melatonin receptor type 1A
General function:
Involved in melatonin receptor activity
Specific function:
High affinity receptor for melatonin. Likely to mediate the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity.
Gene Name:
MTNR1A
Uniprot ID:
O02769
Molecular weight:
29370.0
Enzyme Details
4. Melatonin receptor 1A
General function:
Involved in melatonin receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
B5LED7
Molecular weight:
24008.0
Enzyme Details
5. Melatonin receptor 1A
General function:
Involved in melatonin receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
B5LED8
Molecular weight:
32673.0
Enzyme Details
6. Indoleamine 2,3-dioxygenase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
IDO1
Uniprot ID:
F1N7C5
Molecular weight:
50061.0
Reactions
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails