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Record Information
Version1.0
Created at2022-09-08 08:00:12 UTC
Updated at2022-09-08 08:00:12 UTC
NP-MRD IDNP0264470
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,4r,6r,6as,7s,9ar,9bs)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-4-hydroxy-2-methylbut-2-enoate
Description(3AR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4r,6r,6as,7s,9ar,9bs)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-4-hydroxy-2-methylbut-2-enoate is found in Eupatorium lindleyanum. It was first documented in 2022 (PMID: 36104165). Based on a literature review a significant number of articles have been published on (3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate (PMID: 36104164) (PMID: 36104163) (PMID: 36104162) (PMID: 36104161) (PMID: 36104160) (PMID: 36104159).
Structure
Thumb
Synonyms
ValueSource
(3AR,4R,6R,6as,7S,9ar,9BS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoic acidGenerator
Chemical FormulaC20H26O8
Average Mass394.4200 Da
Monoisotopic Mass394.16277 Da
IUPAC Name(3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate
Traditional Name(3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C(=C\CO)C(=O)O[C@@H]1C[C@](O)(CO)[C@@H]2[C@@H](O)C=C(C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@H]12
InChI Identifier
InChI=1S/C20H26O8/c1-9(4-5-21)18(24)27-13-7-20(26,8-22)16-12(23)6-10(2)14(16)17-15(13)11(3)19(25)28-17/h4,6,12-17,21-23,26H,3,5,7-8H2,1-2H3/b9-4-/t12-,13+,14-,15+,16+,17-,20-/m0/s1
InChI KeyBWFIEPPPOFKOKO-PIWZHLCHSA-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 lindleyanumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Sesquiterpenoid
  • Guaiane sesquiterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP-0.67ChemAxon
pKa (Strongest Acidic)13.48ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.04 m³·mol⁻¹ChemAxon
Polarizability38.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 Compound163004831
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
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  15. LOTUS database [Link]