Showing metabocard for Sumatriptan (BMDB0005037)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:55 UTC
Update Date2020-05-11 19:32:27 UTC
BMDB IDBMDB0005037
Secondary Accession Numbers
  • BMDB05037
Metabolite Identification
Common NameSumatriptan
DescriptionSumatriptan, also known as imigran or imitrex, 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. Sumatriptan is a very strong basic compound (based on its pKa). Sumatriptan is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamideChEBI
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamideChEBI
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamideChEBI
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamideChEBI
ImigranChEBI
ImitrexChEBI
SumatranChEBI
SumatriptanumChEBI
SumaxChEBI
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamideGenerator
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamideGenerator
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamideGenerator
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamideGenerator
Imigran recoveryHMDB
Glaxo wellcome brand OF sumatriptanHMDB
Sumatriptan GSK brandHMDB
GSK Brand OF sumatriptanHMDB
Sumatriptan succinateHMDB
Succinate, sumatriptanHMDB
Chemical FormulaC14H21N3O2S
Average Molecular Weight295.4
Monoisotopic Molecular Weight295.135447621
IUPAC Name1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
Traditional Namesumatriptan
CAS Registry Number103628-46-2
SMILES
CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1
InChI Identifier
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
InChI KeyKQKPFRSPSRPDEB-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
  • Aralkylamine
  • Substituted pyrrole
  • Organic sulfonic acid amide
  • Benzenoid
  • Organosulfonic acid amide
  • Pyrrole
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.93ADLARD,M ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.17ALOGPS
logP0.74ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.08 m³·mol⁻¹ChemAxon
Polarizability32.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-7390000000-5809ad2270f77ffcec79View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0190000000-c12ee3ac5f29c3420996View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0390000000-cdddf05865e6d570c337View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-1090000000-b0360ed354c3c7a76195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-7970000000-4a9c99ffaf927876bb55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0090000000-42a6041e68fbb33f3c3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1290000000-18f63d6714d369042cedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-1910000000-b311f02f2295ff294573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3090000000-23dacc0baf4eac1e818aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mo-9280000000-45a6f0dbb82744e4f102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-9120000000-ca48d4e064a2f6323651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000000-a75e9a0167fac95c8ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9530000000-af10011e851a42315cd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-e271d3cf647593f64e67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-7a6d991d417845eb044cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg4-2890000000-0b86cdf68f0a940df967View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9510000000-e92db5fc8036751fb26fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9400000000-93cc7dc7e521f98aa292View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005037
DrugBank IDDB00669
Phenol Explorer Compound IDNot Available
FooDB IDFDB023604
KNApSAcK IDNot Available
Chemspider ID5165
KEGG Compound IDC07319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSumatriptan
METLIN ID2612
PubChem Compound5358
PDB IDNot Available
ChEBI ID10650
References
Synthesis ReferenceTorner Montoya, Miguel. Process for the synthesis of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide [sumatriptan]. Span. (1994), 6 pp. CODEN: SPXXAD ES 2059236 A1 19941101 CAN 122:265245 AN 1995:520544
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available