Showing metabocard for 5-Methoxytryptamine (BMDB0004095)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:54 UTC
Update Date2020-05-11 22:30:23 UTC
BMDB IDBMDB0004095
Secondary Accession Numbers
  • BMDB04095
Metabolite Identification
Common Name5-Methoxytryptamine
Description5-Methoxytryptamine, also known as mexamine or 5-meot, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. 5-Methoxytryptamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(5-Methoxyindol-3-yl)ethylamineChEBI
3-(2-Aminoethyl)-5-methoxyindoleChEBI
5-MeOTChEBI
5-Methoxy-1H-indole-3-ethanamineChEBI
5-MTChEBI
5MOTChEBI
MexamineChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanamineHMDB
5-MotHMDB
Lopac-m-6628HMDB
MeksaminHMDB
MethoxytryptamineHMDB
Mexamine baseHMDB
MeksamineHMDB
5 MethoxytryptamineHMDB
5-MethoxytryptamineChEBI
Chemical FormulaC11H14N2O
Average Molecular Weight190.2417
Monoisotopic Molecular Weight190.11061308
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
Traditional Name5 methoxytryptamine
CAS Registry Number608-07-1
SMILES
COC1=CC2=C(NC=C2CCN)C=C1
InChI Identifier
InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
InChI KeyJTEJPPKMYBDEMY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Anisole
  • 2-arylethylamine
  • Alkyl aryl ether
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.41ALOGPS
logP1.33ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)17.45ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area51.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.84 m³·mol⁻¹ChemAxon
Polarizability21.32 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-MS (2 TMS)splash10-0ue9-1960000000-9d22140ff2b48f31db09View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-3900000000-b121de7d00a382123401View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-1960000000-9d22140ff2b48f31db09View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-3900000000-b121de7d00a382123401View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-a5fe7e3acae8eed474deView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-2b80fe48b74acca6bebfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-c9d325a89238b38270a6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dr-0900000000-ac5e7141a1f9a408fc34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0900000000-6e5b3b429a1bb70ffaf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-0900000000-e60ae04a11b9e498a966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-54e5a7201f25456dcad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-1900000000-293475115ff46b97099aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-a14a529194c5227e34f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-002f-0900000000-ad73b33b853950cd5689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-54e5a7201f25456dcad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-adf7f816d92642625bddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-a14a529194c5227e34f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-0900000000-ad73b33b853950cd5689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-485d7582e65bfa3e31f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-db26f9e0d37f5c251c53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-eaf537b355550eb27e55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-478e855c47b694b99c9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-3096f67fc0f5797d14b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2d015296f43e86be7b7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-2a2466c60f7faa96dccaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-c4f465460bde21d469beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-f1d40ff7aa6c88ecdfd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-0900000000-22d3b9e8cbdb136bcb64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-0900000000-74e1867f5b88bc53f677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-438c89f58ad3c0098959View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Liver
  • Mammary Gland
  • Milk
  • Platelet
  • Ruminal Fluid
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Thyroid GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004095
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023311
KNApSAcK IDNot Available
Chemspider ID1767
KEGG Compound IDC05659
BioCyc IDCPD-12018
BiGG IDNot Available
Wikipedia Link5-Methoxytryptamine
METLIN ID7015
PubChem Compound1833
PDB IDNot Available
ChEBI ID2089
References
Synthesis ReferenceSzmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]