Np mrd loader

Record Information
Version2.0
Created at2022-09-06 20:59:43 UTC
Updated at2022-09-06 20:59:44 UTC
NP-MRD IDNP0237757
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one
DescriptionZanthodioline belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Zanthodioline is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Zanthodioline has been detected, but not quantified in, fruits and herbs and spices. 3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3h,4h-pyrano[3,2-c]quinolin-5-one is found in Zanthoxylum beecheyanum and Zanthoxylum simulans. This could make zanthodioline a potential biomarker for the consumption of these foods.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H19NO5
Average Mass305.3258 Da
Monoisotopic Mass305.12632 Da
IUPAC Name3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one
Traditional Name3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3H,4H-pyrano[3,2-c]quinolin-5-one
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O
InChI Identifier
InChI=1S/C16H19NO5/c1-16(2)14(19)12(18)10-13(22-16)8-6-5-7-9(21-4)11(8)17(3)15(10)20/h5-7,12,14,18-19H,1-4H3
InChI KeyGQGXEILPTLCMFO-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
Zanthoxylum beecheyanumLOTUS Database
Zanthoxylum simulansLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentPyranoquinolines
Alternative Parents
Substituents
  • Pyranoquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyranopyridine
  • Anisole
  • Alkyl aryl ether
  • Pyridinone
  • Pyran
  • Pyridine
  • Benzenoid
  • Vinylogous ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactam
  • 1,2-diol
  • Azacycle
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • 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
logP0.82ALOGPS
logP-0.27ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.35 m³·mol⁻¹ChemAxon
Polarizability31.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031929
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008617
KNApSAcK IDC00026497
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78384601
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]