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Record Information
Version2.0
Created at2022-09-06 22:55:58 UTC
Updated at2022-09-06 22:55:58 UTC
NP-MRD IDNP0239354
Secondary Accession NumbersNone
Natural Product Identification
Common Name[9-(acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-4h,5h,7h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl acetate
Description[9-(Acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-2H,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl acetate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. [9-(acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-4h,5h,7h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl acetate is found in Artemisia ludoviciana. [9-(Acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-2H,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
[9-(Acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-2H,4H,5H,6H,7H,8H,9H,11ah-cyclodeca[b]furan-3-yl]methyl acetic acidGenerator
Chemical FormulaC19H24O8
Average Mass380.3930 Da
Monoisotopic Mass380.14712 Da
IUPAC Name[9-(acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-2H,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl acetate
Traditional Name[9-(acetyloxy)-7-hydroperoxy-10-methyl-6-methylidene-2-oxo-4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC1=C2CCC(=C)C(CC(OC(C)=O)C(C)=CC2OC1=O)OO
InChI Identifier
InChI=1S/C19H24O8/c1-10-5-6-14-15(9-24-12(3)20)19(22)26-18(14)7-11(2)16(25-13(4)21)8-17(10)27-23/h7,16-18,23H,1,5-6,8-9H2,2-4H3
InChI KeyVPUUNRFILDDXAY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia ludovicianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Tricarboxylic acid or derivatives
  • 2-furanone
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Hydroperoxide
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Peroxol
  • Alkyl hydroperoxide
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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
logP1.35ALOGPS
logP1.37ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability38.17 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]