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Record Information
Version3.6
Creation Date2006-08-13 17:42:43 UTC
Update Date2016-02-11 01:06:43 UTC
HMDB IDHMDB04369
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Methylserotonin
DescriptionN-methylserotonin is a product of the serotonin-degradative pathway, found in urine specimens of patients with psychiatric disorders (PubMed ID 8747157 ).
Structure
Thumb
Synonyms
ValueSource
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 KeyInChIKey=ASUSBMNYRHGZIG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as serotonins. These 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
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • 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
Water Solubility0.75 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.13 m3·mol-1ChemAxon
Polarizability21.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-646686588892f9e597f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1900000000-a768b9399c8fcac6cd0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-2900000000-543fe5365e1fa682b60eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b4a2e8f1bf6e3e782690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-970029b3b4e6dd32e53aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-9851a5693e2c284d3b9dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB017273
KNApSAcK IDNot Available
Chemspider ID132989
KEGG Compound IDC06212
BioCyc IDNot Available
BiGG ID47668
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04369
Metagene LinkHMDB04369
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 References
  1. Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [8747157 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695
Reactions
S-Adenosylmethionine + Serotonin → S-Adenosylhomocysteine + N-Methylserotonindetails