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Record Information
Version1.0
Created at2021-06-19 21:28:40 UTC
Updated at2021-06-29 23:57:43 UTC
NP-MRD IDNP0030006
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,11(13)-Isodaucadien-12,5-olide
Provided ByJEOL DatabaseJEOL Logo
Description(5AS,10aR,10bS)-5a,9-dimethyl-3-methylidene-2H,3H,4H,5H,5aH,6H,7H,8H,10bH-azuleno[3a,3-b]furan-2-one 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. 6,11(13)-Isodaucadien-12,5-olide is found in Laurus nobilis. It was first documented in 2006 (Dall'Acqua, S., et al.). Based on a literature review very few articles have been published on (5aS,10aR,10bS)-5a,9-dimethyl-3-methylidene-2H,3H,4H,5H,5aH,6H,7H,8H,10bH-azuleno[3a,3-b]furan-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H20O2
Average Mass232.3230 Da
Monoisotopic Mass232.14633 Da
IUPAC Name(5aS,10aR,10bS)-5a,9-dimethyl-3-methylidene-2H,3H,4H,5H,5aH,6H,7H,8H,10bH-azuleno[3a,3-b]furan-2-one
Traditional Name(5aS,10aR,10bS)-5a,9-dimethyl-3-methylidene-4H,5H,6H,7H,8H,10bH-azuleno[3a,3-b]furan-2-one
CAS Registry NumberNot Available
SMILES
[H]C([H])=C1C(=O)O[C@@]23C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]13[H]
InChI Identifier
InChI=1S/C15H20O2/c1-10-5-4-7-14(3)8-6-12-11(2)13(16)17-15(12,14)9-10/h9,12H,2,4-8H2,1,3H3/t12-,14-,15+/m0/s1
InChI KeyUXTXADQJTURZKJ-AEGPPILISA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Laurus nobilis L.
    • Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006)
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
  • Gamma butyrolactone
  • Oxolane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • 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
logP3.96ALOGPS
logP3.68ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.97 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17240762
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16082053
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dall'Acqua, S., et al. (2006). Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006). Chem. Pharm. Bull..