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Record Information
Version2.0
Created at2022-09-08 14:25:35 UTC
Updated at2022-09-08 14:25:35 UTC
NP-MRD IDNP0269096
Secondary Accession NumbersNone
Natural Product Identification
Common Name5''-(furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-7'-yl acetate
Description5''-(Furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-7'-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5''-(furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-7'-yl acetate is found in Teucrium polium. 5''-(Furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-7'-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
5''-(Furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-7'-yl acetic acidGenerator
Chemical FormulaC22H26O8
Average Mass418.4420 Da
Monoisotopic Mass418.16277 Da
IUPAC Name5''-(furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-7'-yl acetate
Traditional Name5''-(furan-3-yl)-8'a-(hydroxymethyl)-6'-methyl-2'',8'-dioxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-7'-yl acetate
CAS Registry NumberNot Available
SMILES
CC1C(OC(C)=O)C(=O)C2(CO)C(CCCC22CO2)C11CC(OC1=O)C1=COC=C1
InChI Identifier
InChI=1S/C22H26O8/c1-12-17(29-13(2)24)18(25)22(10-23)16(4-3-6-20(22)11-28-20)21(12)8-15(30-19(21)26)14-5-7-27-9-14/h5,7,9,12,15-17,23H,3-4,6,8,10-11H2,1-2H3
InChI KeyPRXJLJDCUBFXSN-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
Teucrium poliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative Parents
Substituents
  • Diterpene lactone
  • Diterpenoid
  • Clerodane diterpenoid
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Furan
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Organooxygen 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
logP1.35ALOGPS
logP1.49ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.74ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.57 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.92 m³·mol⁻¹ChemAxon
Polarizability41.21 ųChemAxon
Number of Rings5ChemAxon
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]