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Record Information
Version1.0
Created at2022-09-05 22:06:40 UTC
Updated at2022-09-05 22:06:40 UTC
NP-MRD IDNP0220721
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,4'as,5'r,5''s,6'r,8'as)-5''-(furan-3-yl)-6'-methyl-2',2'',8'-trioxo-tetrahydro-3'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate
Description4Alpha,18-Epoxytafricanin A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (2r,4'as,5'r,5''s,6'r,8'as)-5''-(furan-3-yl)-6'-methyl-2',2'',8'-trioxo-tetrahydro-3'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate is found in Teucrium pestalozzae, Teucrium racemosum and Teucrium trifidum. Based on a literature review very few articles have been published on 4alpha,18-Epoxytafricanin A.
Structure
Thumb
Synonyms
ValueSource
4a,18-Epoxytafricanin aGenerator
4Α,18-epoxytafricanin aGenerator
Chemical FormulaC22H24O8
Average Mass416.4260 Da
Monoisotopic Mass416.14712 Da
IUPAC Name[(2R,4'aS,5'R,5''S,6'R,8'aS)-5''-(furan-3-yl)-6'-methyl-2',2'',8'-trioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate
Traditional Name(2R,4'aS,5'R,5''S,6'R,8'aS)-5''-(furan-3-yl)-6'-methyl-2',2'',8'-trioxo-tetrahydro-3'H-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC(=O)[C@]2(COC(C)=O)[C@H](CCC(=O)[C@]22CO2)[C@@]11C[C@H](OC1=O)C1=COC=C1
InChI Identifier
InChI=1S/C22H24O8/c1-12-7-18(25)21(10-28-13(2)23)16(3-4-17(24)22(21)11-29-22)20(12)8-15(30-19(20)26)14-5-6-27-9-14/h5-6,9,12,15-16H,3-4,7-8,10-11H2,1-2H3/t12-,15+,16-,20-,21+,22-/m1/s1
InChI KeyUALFLPWLEQXRGU-LCJNUFCQSA-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 pestalozzaeLOTUS Database
Teucrium racemosumLOTUS Database
Teucrium trifidumLOTUS 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
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP1.78ChemAxon
pKa (Strongest Acidic)18.15ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area112.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.05 m³·mol⁻¹ChemAxon
Polarizability40.95 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 Compound14543736
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]