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Record Information
Version2.0
Created at2022-09-10 01:48:12 UTC
Updated at2022-09-10 01:48:12 UTC
NP-MRD IDNP0293670
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-11-ol
Description6,14,15-Trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system. 6,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2(7),3,5,8,10,12,14-octaen-11-ol is found in Aristolochia argentina, Aristolochia taliscana, Dasymaschalon blumei, Friesodielsia velutina, Goniothalamus griffithii, Goniothalamus sesquipedalis and Uvaria microcarpa. 6,14,15-Trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1,3,5,7,9(16),10,12,14-octaen-11-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H15NO4
Average Mass309.3210 Da
Monoisotopic Mass309.10011 Da
IUPAC Name6,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one
Traditional Name6,14,15-trimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C3C(NC2=O)=CC2=C(OC)C=CC=C2C3=C1OC
InChI Identifier
InChI=1S/C18H15NO4/c1-21-13-6-4-5-9-10(13)7-12-15-11(18(20)19-12)8-14(22-2)17(23-3)16(9)15/h4-8H,1-3H3,(H,19,20)
InChI KeyDCWZBQMWCAMEEF-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
Aristolochia argentinaLOTUS Database
Aristolochia taliscanaLOTUS Database
Dasymaschalon blumeiLOTUS Database
Friesodielsia velutinaLOTUS Database
Goniothalamus griffithiiLOTUS Database
Goniothalamus sesquipedalisLOTUS Database
Uvaria microcarpaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAristolactams
Sub ClassNot Available
Direct ParentAristolactams
Alternative Parents
Substituents
  • Aristolactam
  • Phenanthrene
  • Isoindolone
  • Naphthalene
  • Indole or derivatives
  • Isoindole or derivatives
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP3.12ALOGPS
logP2.6ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.39ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.79 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.82 m³·mol⁻¹ChemAxon
Polarizability32.38 ųChemAxon
Number of Rings4ChemAxon
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 Compound10859838
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]