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Record Information
Version2.0
Created at2022-09-12 00:53:27 UTC
Updated at2022-09-12 00:53:27 UTC
NP-MRD IDNP0322231
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate
Description(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6,9-trismethylene-4beta-hydroxy-8alpha-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4s,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate is found in Centaurea scoparia. Based on a literature review very few articles have been published on (3aR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6,9-trismethylene-4beta-hydroxy-8alpha-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-one.
Structure
Thumb
Synonyms
ValueSource
(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6,9-trismethylene-4b-hydroxy-8a-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-oneGenerator
(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6,9-trismethylene-4β-hydroxy-8α-(benzoyloxy)azuleno[4,5-b]furan-2(3H)-oneGenerator
Chemical FormulaC22H22O5
Average Mass366.4130 Da
Monoisotopic Mass366.14672 Da
IUPAC Name(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoate
Traditional Name(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate
CAS Registry NumberNot Available
SMILES
O[C@H]1CC(=C)[C@@H]2C[C@H](OC(=O)C3=CC=CC=C3)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12
InChI Identifier
InChI=1S/C22H22O5/c1-11-9-16(23)19-13(3)21(24)27-20(19)18-12(2)17(10-15(11)18)26-22(25)14-7-5-4-6-8-14/h4-8,15-20,23H,1-3,9-10H2/t15-,16-,17-,18-,19+,20+/m0/s1
InChI KeyUIIZHPJVPKARSE-GFLQDLJJSA-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
Centaurea scopariaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Sesquiterpenoid
  • Guaiane sesquiterpenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Benzenoid
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP2.99ChemAxon
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.88 m³·mol⁻¹ChemAxon
Polarizability38.26 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 Compound100927643
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]