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Record Information
Version2.0
Created at2022-09-10 00:08:41 UTC
Updated at2022-09-10 00:08:42 UTC
NP-MRD IDNP0292561
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r,3ar,4r,9r,11ar)-9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate
Description(E)-2-Methyl-2-butenoic acid (3R,6Z,10Z)-2-oxo-3alpha,10-dimethyl-6-(hydroxymethyl)-9beta-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4alpha-yl ester belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (3r,3ar,4r,9r,11ar)-9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate is found in Eupatorium perfoliatum. Based on a literature review very few articles have been published on (E)-2-Methyl-2-butenoic acid (3R,6Z,10Z)-2-oxo-3alpha,10-dimethyl-6-(hydroxymethyl)-9beta-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4alpha-yl ester.
Structure
Thumb
Synonyms
ValueSource
(e)-2-Methyl-2-butenoate (3R,6Z,10Z)-2-oxo-3a,10-dimethyl-6-(hydroxymethyl)-9b-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4a-yl esterGenerator
(e)-2-Methyl-2-butenoate (3R,6Z,10Z)-2-oxo-3alpha,10-dimethyl-6-(hydroxymethyl)-9beta-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4alpha-yl esterGenerator
(e)-2-Methyl-2-butenoate (3R,6Z,10Z)-2-oxo-3α,10-dimethyl-6-(hydroxymethyl)-9β-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4α-yl esterGenerator
(e)-2-Methyl-2-butenoic acid (3R,6Z,10Z)-2-oxo-3a,10-dimethyl-6-(hydroxymethyl)-9b-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4a-yl esterGenerator
(e)-2-Methyl-2-butenoic acid (3R,6Z,10Z)-2-oxo-3α,10-dimethyl-6-(hydroxymethyl)-9β-hydroxy-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4α-yl esterGenerator
Chemical FormulaC20H28O6
Average Mass364.4380 Da
Monoisotopic Mass364.18859 Da
IUPAC Name(3R,3aR,4R,9R,11aR)-9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name(3R,3aR,4R,9R,11aR)-9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(/C)C(=O)O[C@@H]1C\C(CO)=C\C[C@@H](O)\C(C)=C/[C@H]2OC(=O)[C@H](C)[C@H]12
InChI Identifier
InChI=1S/C20H28O6/c1-5-11(2)19(23)25-17-9-14(10-21)6-7-15(22)12(3)8-16-18(17)13(4)20(24)26-16/h5-6,8,13,15-18,21-22H,7,9-10H2,1-4H3/b11-5+,12-8-,14-6-/t13-,15-,16-,17-,18+/m1/s1
InChI KeyQQVBXEPCEBPLSG-XRTDFEGJSA-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
Eupatorium perfoliatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Oxolane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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
logP2.03ChemAxon
pKa (Strongest Acidic)14.46ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.83 m³·mol⁻¹ChemAxon
Polarizability39.09 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 Compound101794218
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]