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Record Information
Version2.0
Created at2022-09-12 04:32:13 UTC
Updated at2022-09-12 04:32:13 UTC
NP-MRD IDNP0324451
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r,3as,5r,6s,7s,8s,8ar)-7-[(2e)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-8-yl (2e)-2-methylbut-2-enoate
Description(3R,3aS,5R,6S,7S,8S,8aR)-7-[(2E)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-8-yl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (3r,3as,5r,6s,7s,8s,8ar)-7-[(2e)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-8-yl (2e)-2-methylbut-2-enoate is found in Ratibida columnifera. Based on a literature review very few articles have been published on (3R,3aS,5R,6S,7S,8S,8aR)-7-[(2E)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-8-yl (2E)-2-methylbut-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(3R,3AS,5R,6S,7S,8S,8ar)-7-[(2E)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-8-yl (2E)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC20H28O7
Average Mass380.4370 Da
Monoisotopic Mass380.18350 Da
IUPAC Name(3R,3aS,5R,6S,7S,8S,8aR)-7-[(2E)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-8-yl (2E)-2-methylbut-2-enoate
Traditional Name(3R,3aS,5R,6S,7S,8S,8aR)-7-[(2E)-but-2-enoyl]-5,7-dihydroxy-3,6-dimethyl-2-oxo-hexahydro-3H-cyclohepta[b]furan-8-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C\C(=O)[C@]1(O)[C@@H](C)[C@H](O)C[C@H]2[C@@H](C)C(=O)O[C@H]2[C@@H]1OC(=O)C(\C)=C\C
InChI Identifier
InChI=1S/C20H28O7/c1-6-8-15(22)20(25)12(5)14(21)9-13-11(4)19(24)26-16(13)17(20)27-18(23)10(3)7-2/h6-8,11-14,16-17,21,25H,9H2,1-5H3/b8-6+,10-7+/t11-,12+,13+,14-,16-,17+,20-/m1/s1
InChI KeyFOOMGPWPPFKITL-INUUIOMRSA-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
Ratibida columnarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Xanthane sesquiterpenoid
  • Fatty acid ester
  • Gamma butyrolactone
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Acryloyl-group
  • Alpha,beta-unsaturated carboxylic ester
  • Alpha,beta-unsaturated ketone
  • Enone
  • Alpha-hydroxy ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • 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
logP2.68ChemAxon
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.29 m³·mol⁻¹ChemAxon
Polarizability38.98 ųChemAxon
Number of Rings2ChemAxon
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 Compound162914440
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]