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Record Information
Version1.0
Created at2022-09-12 07:17:36 UTC
Updated at2022-09-12 07:17:37 UTC
NP-MRD IDNP0326061
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-(acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-octahydronaphtho[2,3-b]furan-4-yl acetate
Description8-(Acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-4-yl acetate belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 8-(acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-octahydronaphtho[2,3-b]furan-4-yl acetate is found in Gonospermum gomerae. 8-(Acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
8-(Acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-4-yl acetic acidGenerator
Chemical FormulaC19H26O7
Average Mass366.4100 Da
Monoisotopic Mass366.16785 Da
IUPAC Name8-(acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-4-yl acetate
Traditional Name8-(acetyloxy)-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-octahydronaphtho[2,3-b]furan-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1CCC(C)(O)C2C(OC(C)=O)C3C(CC12C)OC(=O)C3=C
InChI Identifier
InChI=1S/C19H26O7/c1-9-14-12(26-17(9)22)8-18(4)13(24-10(2)20)6-7-19(5,23)16(18)15(14)25-11(3)21/h12-16,23H,1,6-8H2,2-5H3
InChI KeyCHXVTGFPYRYMMI-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
Gonospermum gomeraeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Tricarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP1.24ALOGPS
logP0.74ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.39 m³·mol⁻¹ChemAxon
Polarizability37.66 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 Compound14109615
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]