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Record Information
Version2.0
Created at2022-09-06 23:01:08 UTC
Updated at2022-09-06 23:01:09 UTC
NP-MRD IDNP0239420
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,4r,7r,9s,11ar)-7,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,7h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate
DescriptionHelivypolide 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,4r,7r,9s,11ar)-7,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,7h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Helianthus annuus. Based on a literature review very few articles have been published on Helivypolide A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H26O6
Average Mass362.4220 Da
Monoisotopic Mass362.17294 Da
IUPAC Name(3aS,4R,7R,9S,11aR)-7,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name(3aS,4R,7R,9S,11aR)-7,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)O[C@@H]1\C=C(C)/[C@H](O)C[C@H](O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12
InChI Identifier
InChI=1S/C20H26O6/c1-6-10(2)19(23)25-16-7-11(3)14(21)9-15(22)12(4)8-17-18(16)13(5)20(24)26-17/h6-8,14-18,21-22H,5,9H2,1-4H3/b10-6-,11-7-,12-8-/t14-,15+,16-,17-,18-/m1/s1
InChI KeyABJWHYSCCHJFPV-JQSMLTMGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus annuusLOTUS 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
  • Alpha,beta-unsaturated carboxylic ester
  • Tetrahydrofuran
  • Enoate ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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
logP2.31ChemAxon
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.18 m³·mol⁻¹ChemAxon
Polarizability37.53 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 Compound102445838
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]