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Record Information
Version2.0
Created at2022-09-12 06:35:43 UTC
Updated at2022-09-12 06:35:43 UTC
NP-MRD IDNP0325670
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,11s,12r,13r,14e,16s,19s,21s)-10-{3-ethyl-8-methoxy-6h,7h-indolo[2,3-a]quinolizin-2-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,9-tetraen-16-ium
Description(1S,11S,12R,13R,14E,16S,19S,21S)-10-{5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1,3,5,10,12,14,16-heptaen-4-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6,9-tetraen-16-ium belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (1s,11s,12r,13r,14e,16s,19s,21s)-10-{3-ethyl-8-methoxy-6h,7h-indolo[2,3-a]quinolizin-2-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,9-tetraen-16-ium is found in Strychnos guianensis. Based on a literature review very few articles have been published on (1S,11S,12R,13R,14E,16S,19S,21S)-10-{5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1,3,5,10,12,14,16-heptaen-4-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6,9-tetraen-16-ium.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H43N4O3
Average Mass627.8080 Da
Monoisotopic Mass627.33297 Da
IUPAC Name(1S,11S,12R,13R,14E,16S,19S,21S)-10-{3-ethyl-8-methoxy-6H,7H-indolo[2,3-a]quinolizin-2-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,9-tetraen-16-ium
Traditional Name(1S,11S,12R,13R,14E,16S,19S,21S)-10-{3-ethyl-8-methoxy-6H,7H-indolo[2,3-a]quinolizin-2-yl}-11-hydroxy-14-(2-hydroxyethylidene)-16-methyl-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,9-tetraen-16-ium
CAS Registry NumberNot Available
SMILES
CCC1=CN2CCC3=C4C(C=CC=C4OC)=NC3=C2C=C1C1=CN2[C@H]3[C@H]([C@@H]1O)[C@H]1C[C@H]4[C@@]3(CC[N@@+]4(C)C\C1=C\CO)C1=CC=CC=C21
InChI Identifier
InChI=1S/C40H43N4O3/c1-4-23-20-42-15-12-25-35-30(9-7-11-33(35)47-3)41-37(25)32(42)18-26(23)28-21-43-31-10-6-5-8-29(31)40-14-16-44(2)22-24(13-17-45)27(19-34(40)44)36(38(28)46)39(40)43/h5-11,13,18,20-21,27,34,36,38-39,45-46H,4,12,14-17,19,22H2,1-3H3/q+1/b24-13-/t27-,34-,36-,38+,39-,40+,44-/m0/s1
InChI KeyMPBXTVZTOPAKIA-ZDVRGJGESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Strychnos guianensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassStrychnos alkaloids
Sub ClassNot Available
Direct ParentStrychnos alkaloids
Alternative Parents
Substituents
  • Strychnan skeleton
  • Akuammicine-skeleton
  • Stemmadenine-skeleton
  • Curan skeleton
  • Carbazole
  • Bipyridine
  • Quinolizine
  • Indolizidine
  • Indole or derivatives
  • Tertiary aliphatic/aromatic amine
  • Anisole
  • Aralkylamine
  • Tetrahydropyridine
  • Dihydropyridine
  • Alkyl aryl ether
  • Benzenoid
  • N-alkylpyrrolidine
  • Piperidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Allylamine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Enamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic cation
  • 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-2.6ChemAxon
pKa (Strongest Acidic)14.16ChemAxon
pKa (Strongest Basic)8.1ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity204.47 m³·mol⁻¹ChemAxon
Polarizability73.28 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
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 Compound163185501
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]