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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:24 UTC
Update Date2019-07-23 07:15:34 UTC
HMDB IDHMDB0061011
Secondary Accession Numbers
  • HMDB61011
Metabolite Identification
Common NameN-desmethylalmotriptan
DescriptionN-desmethylalmotriptan 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. Almotriptan, is a triptan drug discovered and developed by Almirall for the treatment of heavy migraine headache. N-desmethylalmotriptan is a very strong basic compound (based on its pKa). N-desmethylalmotriptan is a metabolite of almotriptan. It is available in 12.5 mg in most countries and also 6.25 mg in US and Canada.
Structure
Data?1563866134
SynonymsNot Available
Chemical FormulaC16H23N3O2S
Average Molecular Weight321.438
Monoisotopic Molecular Weight321.151097685
IUPAC Namemethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
Traditional Namemethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
CAS Registry Number334981-12-3
SMILES
CNCCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C2
InChI Identifier
InChI=1S/C16H23N3O2S/c1-17-7-6-14-11-18-16-5-4-13(10-15(14)16)12-22(20,21)19-8-2-3-9-19/h4-5,10-11,17-18H,2-3,6-9,12H2,1H3
InChI KeyIREINZNGILEJRP-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
  • Organosulfonic acid amide
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.52ALOGPS
logP1.14ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.23 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.79331661259
DarkChem[M-H]-172.83931661259
DeepCCS[M+H]+176.2430932474
DeepCCS[M-H]-173.88230932474
DeepCCS[M-2H]-206.76730932474
DeepCCS[M+Na]+182.33330932474
AllCCS[M+H]+175.632859911
AllCCS[M+H-H2O]+172.432859911
AllCCS[M+NH4]+178.432859911
AllCCS[M+Na]+179.232859911
AllCCS[M-H]-176.032859911
AllCCS[M+Na-2H]-176.232859911
AllCCS[M+HCOO]-176.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-desmethylalmotriptanCNCCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C24619.2Standard polar33892256
N-desmethylalmotriptanCNCCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C23119.6Standard non polar33892256
N-desmethylalmotriptanCNCCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C23098.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-desmethylalmotriptan,1TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C3095.1Semi standard non polar33892256
N-desmethylalmotriptan,1TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C3002.2Standard non polar33892256
N-desmethylalmotriptan,1TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C4170.3Standard polar33892256
N-desmethylalmotriptan,1TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C122926.0Semi standard non polar33892256
N-desmethylalmotriptan,1TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C122880.3Standard non polar33892256
N-desmethylalmotriptan,1TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C124119.8Standard polar33892256
N-desmethylalmotriptan,2TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C3072.7Semi standard non polar33892256
N-desmethylalmotriptan,2TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C3127.1Standard non polar33892256
N-desmethylalmotriptan,2TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C3897.9Standard polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C3332.7Semi standard non polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C3385.0Standard non polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C4245.4Standard polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C123134.0Semi standard non polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C123182.6Standard non polar33892256
N-desmethylalmotriptan,1TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C124128.2Standard polar33892256
N-desmethylalmotriptan,2TBDMS,isomer #1CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C3510.4Semi standard non polar33892256
N-desmethylalmotriptan,2TBDMS,isomer #1CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C3728.5Standard non polar33892256
N-desmethylalmotriptan,2TBDMS,isomer #1CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C12)[Si](C)(C)C(C)(C)C3945.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethylalmotriptan GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-c69c07ff71a4e97ff9212017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethylalmotriptan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 10V, Positive-QTOFsplash10-00di-2289000000-3a41a83c8b4e4bd6300a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 20V, Positive-QTOFsplash10-00di-9851000000-bf1c0ae4e67cb62931882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 40V, Positive-QTOFsplash10-05fu-9600000000-bbd70f9bdc9ffa380e032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 10V, Negative-QTOFsplash10-0089-2916000000-b4b21fbc232ff3b95c3f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 20V, Negative-QTOFsplash10-0089-3931000000-bff0a4950ac639ce8b2b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 40V, Negative-QTOFsplash10-03di-9310000000-7fd469ffbda623deb1742016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 10V, Negative-QTOFsplash10-00e9-0709000000-a69010c062e9dd8f577c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 20V, Negative-QTOFsplash10-02n9-3419000000-c50bccd6cf003763e86e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 40V, Negative-QTOFsplash10-03fr-5982000000-c235867fa287da87f3282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 10V, Positive-QTOFsplash10-00di-0039000000-d8b741f15bdf95734b802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 20V, Positive-QTOFsplash10-0006-0693000000-9ee2bbeaad887e7b7c632021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylalmotriptan 40V, Positive-QTOFsplash10-059x-5920000000-41bff879d3786b45f9b12021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71315712
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available