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Record Information
Version2.0
Created at2022-09-07 02:07:31 UTC
Updated at2022-09-07 02:07:32 UTC
NP-MRD IDNP0241932
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,10s,13r,14s,16s)-18-(acetyloxy)-8,14-dimethyl-15-oxido-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraene-8,15-diium-13-carboxylate
DescriptionCHEMBL3351040 belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. (1r,10s,13r,14s,16s)-18-(acetyloxy)-8,14-dimethyl-15-oxido-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraene-8,15-diium-13-carboxylate is found in Alstonia yunnanensis. Based on a literature review very few articles have been published on CHEMBL3351040.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H24N2O5
Average Mass396.4430 Da
Monoisotopic Mass396.16852 Da
IUPAC Name(1R,10S,13R,14S,16S)-18-(acetyloxy)-8,14-dimethyl-15-oxido-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraene-8,15-diium-13-carboxylate
Traditional Name(1R,10S,13R,14S,16S)-18-(acetyloxy)-8,14-dimethyl-15-oxido-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraene-8,15-diium-13-carboxylate
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@@H](C2C[C@H]3C4=[N+](C)C5=CC=CC=C5[C@]44C[C@@H](C2C4OC(C)=O)[N+]13[O-])C([O-])=O
InChI Identifier
InChI=1S/C22H24N2O5/c1-10-17(21(26)27)12-8-15-19-22(13-6-4-5-7-14(13)23(19)3)9-16(24(10,15)28)18(12)20(22)29-11(2)25/h4-7,10,12,15-18,20H,8-9H2,1-3H3/t10-,12?,15-,16-,17-,18?,20?,22+,24?/m0/s1
InChI KeyMVVOGBRCQSCYJN-QWWWVCEYSA-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
Alstonia yunnanensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAjmaline-sarpagine alkaloids
Sub ClassNot Available
Direct ParentAjmaline-sarpagine alkaloids
Alternative Parents
Substituents
  • Sarpagine-skeleton
  • Quinolizidine
  • 3-alkylindole
  • Indole or derivatives
  • Piperidinecarboxylic acid
  • Quinuclidine
  • Azepane
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Benzenoid
  • Trialkyl amine oxide
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Trisubstituted n-oxide
  • Propargyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • N-oxide
  • Carboxylic acid
  • Organic salt
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen 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
logP-2.3ChemAxon
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area92.5 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity124.87 m³·mol⁻¹ChemAxon
Polarizability41.15 ųChemAxon
Number of Rings6ChemAxon
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 Compound118719271
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]