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Record Information
Version2.0
Created at2022-09-06 22:44:20 UTC
Updated at2022-09-06 22:44:20 UTC
NP-MRD IDNP0239200
Secondary Accession NumbersNone
Natural Product Identification
Common Name16,17-dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(18),4,6,8,14,16-hexaen-2-one
Description16,17-Dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]Octadeca-1(18),4(9),5,7,14,16-hexaen-2-one belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. 16,17-dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(18),4,6,8,14,16-hexaen-2-one is found in Fumaria vaillantii. 16,17-Dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]Octadeca-1(18),4(9),5,7,14,16-hexaen-2-one is a strong basic compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H23NO5
Average Mass357.4060 Da
Monoisotopic Mass357.15762 Da
IUPAC Name16,17-dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(18),4,6,8,14,16-hexaen-2-one
Traditional Name16,17-dihydroxy-7,8-dimethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(18),4,6,8,14,16-hexaen-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC=C2CC(=O)C3=CC(O)=C(O)C=C3CCN(C)CC2=C1OC
InChI Identifier
InChI=1S/C20H23NO5/c1-21-7-6-13-9-17(23)18(24)10-14(13)16(22)8-12-4-5-19(25-2)20(26-3)15(12)11-21/h4-5,9-10,23-24H,6-8,11H2,1-3H3
InChI KeyKERJSZZMJYDUGO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fumaria vaillantiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtopine alkaloids
Sub ClassNot Available
Direct ParentProtopine alkaloids
Alternative Parents
Substituents
  • Protopine skeleton
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen 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
logP2.37ALOGPS
logP2.42ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.96ChemAxon
pKa (Strongest Basic)4.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.92 m³·mol⁻¹ChemAxon
Polarizability37.64 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]