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Record Information
Version2.0
Created at2022-09-07 19:30:13 UTC
Updated at2022-09-07 19:30:13 UTC
NP-MRD IDNP0255125
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(2r,3s,4s,5r,6s)-6-{[(3ar,4ar,5r,7ar,9ar)-5,8-dimethyl-3-methylidene-2-oxo-3ah,4h,4ah,6h,7h,7ah,9ah-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Description[(2R,3S,4S,5R,6S)-6-{[(3aR,4aR,5R,7aR,9aR)-5,8-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,4aH,5H,6H,7H,7aH,9aH-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate 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. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-{[(3aR,4aR,5R,7aR,9aR)-5,8-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,4aH,5H,6H,7H,7aH,9aH-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(2R,3S,4S,5R,6S)-6-{[(3ar,4ar,5R,7ar,9ar)-5,8-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,4ah,5H,6H,7H,7ah,9ah-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetic acidGenerator
Chemical FormulaC23H32O9
Average Mass452.5000 Da
Monoisotopic Mass452.20463 Da
IUPAC Name[(2R,3S,4S,5R,6S)-6-{[(3aR,4aR,5R,7aR,9aR)-5,8-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,4aH,5H,6H,7H,7aH,9aH-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Traditional Name[(2R,3S,4S,5R,6S)-6-{[(3aR,4aR,5R,7aR,9aR)-5,8-dimethyl-3-methylidene-2-oxo-3aH,4H,4aH,6H,7H,7aH,9aH-azuleno[6,5-b]furan-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@H]1O[C@@H](O[C@]2(C)CC[C@@H]3[C@H]2C[C@H]2[C@H](OC(=O)C2=C)C=C3C)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C23H32O9/c1-10-7-16-14(11(2)21(28)30-16)8-15-13(10)5-6-23(15,4)32-22-20(27)19(26)18(25)17(31-22)9-29-12(3)24/h7,13-20,22,25-27H,2,5-6,8-9H2,1,3-4H3/t13-,14+,15+,16+,17+,18+,19-,20+,22-,23+/m0/s1
InChI KeyDYLLAMCKQXNEAV-DJIPIYEQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Glycosyl compound
  • O-glycosyl compound
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Monosaccharide
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP0.8ChemAxon
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.75 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity110.44 m³·mol⁻¹ChemAxon
Polarizability45.63 ųChemAxon
Number of Rings4ChemAxon
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 Compound162951112
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]