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Record Information
Version2.0
Created at2022-09-10 00:19:40 UTC
Updated at2022-09-10 00:19:40 UTC
NP-MRD IDNP0292683
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,4s,6r,11ar)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoate
Description(3AR,4S,6R,11aR)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoate 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. Based on a literature review very few articles have been published on (3aR,4S,6R,11aR)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(3AR,4S,6R,11ar)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoic acidGenerator
Chemical FormulaC21H28O7
Average Mass392.4480 Da
Monoisotopic Mass392.18350 Da
IUPAC Name(3aR,4S,6R,11aR)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoate
Traditional Name(3aR,4S,6R,11aR)-6-(acetyloxy)-6,10-dimethyl-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylprop-2-enoate
CAS Registry NumberNot Available
SMILES
CC1CCC(=O)[C@@](C)(C[C@H](OC(=O)C(C)=C)[C@H]2[C@@H](C1)OC(=O)C2=C)OC(C)=O
InChI Identifier
InChI=1S/C21H28O7/c1-11(2)19(24)27-16-10-21(6,28-14(5)22)17(23)8-7-12(3)9-15-18(16)13(4)20(25)26-15/h12,15-16,18H,1,4,7-10H2,2-3,5-6H3/t12?,15-,16+,18-,21-/m1/s1
InChI KeyHBRKQMNFEIZZOU-MIOCJGTNSA-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 OriginNot Available
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
  • Sesquiterpenoid
  • Germacrane sesquiterpenoid
  • Tricarboxylic acid or derivatives
  • Alpha-acyloxy ketone
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen 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
logP3.42ChemAxon
pKa (Strongest Acidic)18.77ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area95.97 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.53 m³·mol⁻¹ChemAxon
Polarizability40.07 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 Compound163188949
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]