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Record Information
Version2.0
Created at2022-09-09 23:19:44 UTC
Updated at2022-09-09 23:19:44 UTC
NP-MRD IDNP0292008
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,6'r,7's,8'as)-6'-ethenyl-7'-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizine]-2,6-diol
Description(3S,6'R,7'S,8'aS)-6'-ethenyl-7'-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-2,6-diol 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. (3s,6'r,7's,8'as)-6'-ethenyl-7'-{[(1s)-2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizine]-2,6-diol is found in Strychnos usambarensis. Based on a literature review very few articles have been published on (3S,6'R,7'S,8'aS)-6'-ethenyl-7'-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-2,6-diol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H34N4O2
Average Mass482.6280 Da
Monoisotopic Mass482.26818 Da
IUPAC Name(3S,6'R,7'S,8'aS)-6'-ethenyl-7'-{[(1S)-2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-2,6-diol
Traditional Name(3S,6'R,7'S,8'aS)-6'-ethenyl-7'-{[(1S)-2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-2,6-diol
CAS Registry NumberNot Available
SMILES
CN1CCC2=C(NC3=CC=CC=C23)[C@@H]1C[C@@H]1C[C@@H]2N(CC[C@@]22C(O)=NC3=CC(O)=CC=C23)C[C@@H]1C=C
InChI Identifier
InChI=1S/C30H34N4O2/c1-3-18-17-34-13-11-30(23-9-8-20(35)16-25(23)32-29(30)36)27(34)15-19(18)14-26-28-22(10-12-33(26)2)21-6-4-5-7-24(21)31-28/h3-9,16,18-19,26-27,31,35H,1,10-15,17H2,2H3,(H,32,36)/t18-,19+,26-,27-,30-/m0/s1
InChI KeyYAXAQXBFDAJGGS-VJJWTNKHSA-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 Origin
Species NameSourceReference
Strychnos usambarensisLOTUS Database
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
  • Indolizidine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Cyclic carboximidic acid
  • Pyrrolidine
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • 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
logP2.01ChemAxon
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)11.25ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity145.46 m³·mol⁻¹ChemAxon
Polarizability54.76 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound163185902
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]