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Record Information
Version2.0
Created at2022-09-12 02:22:54 UTC
Updated at2022-09-12 02:22:54 UTC
NP-MRD IDNP0323143
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate
DescriptionMethyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. methyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate is found in Tabernaemontana divaricata. Methyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Methyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2,4,6,9-tetraene-10-carboxylic acidGenerator
Methyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylic acidGenerator
Chemical FormulaC23H28N2O6
Average Mass428.4850 Da
Monoisotopic Mass428.19474 Da
IUPAC Namemethyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate
Traditional Namemethyl 12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate
CAS Registry NumberNot Available
SMILES
CCC12CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4C33CCN(CC4OC14)C23
InChI Identifier
InChI=1S/C23H28N2O6/c1-5-22-9-11(20(27)30-4)18-23(6-7-25(21(22)23)10-14-19(22)31-14)12-8-13(26)16(28-2)17(29-3)15(12)24-18/h8,14,19,21,24,26H,5-7,9-10H2,1-4H3
InChI KeyNZLKHAMETKWZND-UHFFFAOYSA-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
Ervatamia coronariaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAspidospermatan-type alkaloids
Sub ClassNot Available
Direct ParentAspidospermatan-type alkaloids
Alternative Parents
Substituents
  • Aspidosperma alkaloid
  • Carbazole
  • Indole or derivatives
  • Dihydroindole
  • Indolizidine
  • Anisole
  • Para-oxazepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Epoxypiperidine
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Piperidine
  • N-alkylpyrrolidine
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Pyrrolidine
  • Enoate ester
  • Methyl ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Oxacycle
  • Oxirane
  • Enamine
  • Dialkyl ether
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen 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
logP2.3ALOGPS
logP1.34ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)7.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.79 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.25 m³·mol⁻¹ChemAxon
Polarizability45.05 ųChemAxon
Number of Rings6ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73089926
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]