Showing metabocard for N-Methylserotonin (BMDB0004369)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:22 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0004369
Secondary Accession Numbers
  • BMDB04369
Metabolite Identification
Common NameN-Methylserotonin
DescriptionN-Methylserotonin belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. N-Methylserotonin is possibly soluble (in water) and a very strong basic compound (based on its pKa). N-Methylserotonin and S-adenosylhomocysteine can be biosynthesized from serotonin and S-adenosylmethionine through its interaction with the enzyme indolethylamine N-methyltransferase. In cattle, N-methylserotonin is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Methylserotonin oxalate saltHMDB
3-(2-(Methylamino)ethyl)-1H-indol-5-olHMDB
3-[2-(Methylamino)ethyl]-1H-indol-5-olHMDB
Lopac-m-1514HMDB
Chemical FormulaC11H14N2O
Average Molecular Weight190.2417
Monoisotopic Molecular Weight190.11061308
IUPAC Name3-[2-(methylamino)ethyl]-1H-indol-5-ol
Traditional NameN-methylserotonin
CAS Registry Number1134-01-6
SMILES
CNCCC1=CNC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3
InChI KeyASUSBMNYRHGZIG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not 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
logP1.55ALOGPS
logP0.69ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)10.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area48.05 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.13 m³·mol⁻¹ChemAxon
Polarizability21.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004369
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017273
KNApSAcK IDNot Available
Chemspider ID132989
KEGG Compound IDC06212
BioCyc IDNot Available
BiGG ID47668
Wikipedia LinkN-Methylserotonin
METLIN ID7056
PubChem Compound150885
PDB IDNot Available
ChEBI ID48294
References
Synthesis ReferenceSomei, Masanori; Yamada, Fumio; Kurauchi, Takashi; Nagahama, Yoshiyuki; Hasegawa, Masakazu; Yamada, Koji; Teranishi, Sakiko; Sato, Haruhiko; Kaneko, Chikara. The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-m
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phenylethanolamine N-methyltransferase
General function:
Involved in phenylethanolamine N-methyltransferase acti
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P10938
Molecular weight:
30918.0
Reactions
Serotonin + S-Adenosylmethionine → N-Methylserotonin + S-Adenosylhomocysteinedetails