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Record Information
Version2.0
Created at2022-09-06 23:03:42 UTC
Updated at2022-09-06 23:03:42 UTC
NP-MRD IDNP0239455
Secondary Accession NumbersNone
Natural Product Identification
Common Name6a-hydroxy-3,6,9a-trimethyl-4h,5h,6h,7h,8h,9bh-azuleno[4,5-b]furan-2,9-dione
Description6A-hydroxy-3,6,9a-trimethyl-2H,4H,5H,6H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2,9-dione belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). 6a-hydroxy-3,6,9a-trimethyl-4h,5h,6h,7h,8h,9bh-azuleno[4,5-b]furan-2,9-dione is found in Parthenium hysterophorus. 6A-hydroxy-3,6,9a-trimethyl-2H,4H,5H,6H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H20O4
Average Mass264.3210 Da
Monoisotopic Mass264.13616 Da
IUPAC Name6a-hydroxy-3,6,9a-trimethyl-2H,4H,5H,6H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2,9-dione
Traditional Name6a-hydroxy-3,6,9a-trimethyl-4H,5H,6H,7H,8H,9bH-azuleno[4,5-b]furan-2,9-dione
CAS Registry NumberNot Available
SMILES
CC1CCC2=C(C)C(=O)OC2C2(C)C(=O)CCC12O
InChI Identifier
InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h8,12,18H,4-7H2,1-3H3
InChI KeyAEVZZALQJYKVBB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Parthenium hysterophorusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentAmbrosanolides and secoambrosanolides
Alternative Parents
Substituents
  • Ambrosanolide
  • Sesquiterpenoid
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • 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
logP1.38ALOGPS
logP2.09ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.37ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.14 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings3ChemAxon
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 Compound12310868
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]