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Record Information
Version2.0
Created at2022-09-08 07:41:19 UTC
Updated at2022-09-08 07:41:19 UTC
NP-MRD IDNP0264235
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-{3-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]propyl}guanidine
DescriptionTrypargine belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. n-{3-[(1s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]propyl}guanidine was first documented in 2011 (PMID: 22069702). Based on a literature review very few articles have been published on Trypargine (PMID: 27554267).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H21N5
Average Mass271.3680 Da
Monoisotopic Mass271.17970 Da
IUPAC NameN-{3-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]propyl}guanidine
Traditional NameN-{3-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]propyl}guanidine
CAS Registry NumberNot Available
SMILES
NC(=N)NCCC[C@@H]1NCCC2=C1NC1=CC=CC=C21
InChI Identifier
InChI=1S/C15H21N5/c16-15(17)19-8-3-6-13-14-11(7-9-18-13)10-4-1-2-5-12(10)20-14/h1-2,4-5,13,18,20H,3,6-9H2,(H4,16,17,19)/t13-/m0/s1
InChI KeyNMPAXZOTIQZCEM-ZDUSSCGKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Guanidine
  • Organoheterocyclic compound
  • Secondary aliphatic amine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Secondary amine
  • Carboximidamide
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.1ChemAxon
pKa (Strongest Acidic)16.38ChemAxon
pKa (Strongest Basic)12.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area89.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.42 m³·mol⁻¹ChemAxon
Polarizability31.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00049071
Chemspider ID162829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound187306
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shmatova OI, Khrustalev VN, Nenajdenko VG: From Cyclic CF3-ketimines to a Family of Trifluoromethylated Nazlinine and Trypargine Analogues. Org Lett. 2016 Sep 16;18(18):4494-7. doi: 10.1021/acs.orglett.6b02031. Epub 2016 Aug 24. [PubMed:27554267 ]
  2. Cesar-Tognoli LM, Salamoni SD, Tavares AA, Elias CF, Costa JC, Bittencourt JC, Palma MS: Effects of spider venom toxin PWTX-I (6-Hydroxytrypargine) on the central nervous system of rats. Toxins (Basel). 2011 Feb;3(2):142-62. doi: 10.3390/toxins3020142. Epub 2011 Feb 22. [PubMed:22069702 ]
  3. LOTUS database [Link]