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Record Information
Version1.0
Created at2022-09-05 23:13:46 UTC
Updated at2022-09-05 23:13:46 UTC
NP-MRD IDNP0221603
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate
DescriptionIneupatorolide A 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. (3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate is found in Allagopappus dichotomus, Allagopappus viscosissimus, Carpesium glossophyllum and Carpesium nepalense. Based on a literature review very few articles have been published on Ineupatorolide A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H30O6
Average Mass366.4540 Da
Monoisotopic Mass366.20424 Da
IUPAC Name(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-dodecahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate
Traditional Name(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate
CAS Registry NumberNot Available
SMILES
CC[C@@H](C)C(=O)O[C@@H]1[C@H]2OC(=O)C(=C)[C@@H]2CC(=O)[C@H](C)CCC[C@]1(C)O
InChI Identifier
InChI=1S/C20H30O6/c1-6-11(2)18(22)26-17-16-14(13(4)19(23)25-16)10-15(21)12(3)8-7-9-20(17,5)24/h11-12,14,16-17,24H,4,6-10H2,1-3,5H3/t11-,12-,14+,16+,17-,20+/m1/s1
InChI KeyOVXUCZUDXTYPCU-DUGSKPGWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allagopappus dichotomusLOTUS Database
Allagopappus viscosissimusLOTUS Database
Carpesium glossophyllumLOTUS Database
Carpesium nepalenseLOTUS Database
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
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Oxolane
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • 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
logP3.52ChemAxon
pKa (Strongest Acidic)13.95ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.83 m³·mol⁻¹ChemAxon
Polarizability39.02 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 IDC00012341
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101688205
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]