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Record Information
Version1.0
Created at2022-04-28 03:49:35 UTC
Updated at2022-04-28 03:49:36 UTC
NP-MRD IDNP0058459
Secondary Accession NumbersNone
Natural Product Identification
Common NamePeroxysachalinin
Description(3AR,4S,7S,11aS)-7-hydroperoxy-10-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Peroxysachalinin is found in Acanthospermum hispidum , Eupatorium chinense and Eupatorium sachalinense. Based on a literature review very few articles have been published on (3aR,4S,7S,11aS)-7-hydroperoxy-10-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(3AR,4S,7S,11as)-7-hydroperoxy-10-methyl-3,6-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,6H,7H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoic acidGenerator
Chemical FormulaC20H26O8
Average Mass394.4200 Da
Monoisotopic Mass394.16277 Da
IUPAC Name(3aR,4S,7S,11aS)-7-hydroperoxy-10-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
Traditional Name(3aR,4S,7S,11aS)-7-hydroperoxy-10-methyl-3,6-dimethylidene-2-oxo-3aH,4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
CAS Registry NumberNot Available
SMILES
C\C1=C/[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](CC(=C)[C@H](CC1)OO)OC(=O)C(\CO)=C\CO
InChI Identifier
InChI=1S/C20H26O8/c1-11-4-5-15(28-25)12(2)9-17(27-20(24)14(10-22)6-7-21)18-13(3)19(23)26-16(18)8-11/h6,8,15-18,21-22,25H,2-5,7,9-10H2,1H3/b11-8+,14-6+/t15-,16-,17-,18-/m0/s1
InChI KeyXKKROPUZCIUQMV-YUQOPVKLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acanthospermum hispidumPlant
Eupatorium chinenseLOTUS Database
Eupatorium sachalinensePlant
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
  • Sesquiterpenoid
  • Germacrane sesquiterpenoid
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Hydroxy acid
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Hydroperoxide
  • Lactone
  • Carboxylic acid ester
  • Alkyl hydroperoxide
  • Oxacycle
  • Organoheterocyclic compound
  • Peroxol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP1.01ALOGPS
logP1.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.69 m³·mol⁻¹ChemAxon
Polarizability39.78 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 Compound162873613
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available