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Record Information
Version2.0
Created at2022-09-09 23:18:16 UTC
Updated at2022-09-09 23:18:16 UTC
NP-MRD IDNP0291989
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,4as,5r,6s,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-6-{[(2z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate
Description(4S,4aS,5R,6S,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (4s,4as,5r,6s,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-6-{[(2z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Petasites japonicus. Based on a literature review very few articles have been published on (4S,4aS,5R,6S,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(4S,4AS,5R,6S,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acidGenerator
(4S,4AS,5R,6S,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulphanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoateGenerator
(4S,4AS,5R,6S,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulphanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC25H34O7S
Average Mass478.6000 Da
Monoisotopic Mass478.20252 Da
IUPAC Name(4S,4aS,5R,6S,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name(4S,4aS,5R,6S,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-6-{[(2Z)-3-(methylsulfanyl)prop-2-enoyl]oxy}-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
CO[C@@]12C[C@H]3CC[C@H](OC(=O)\C=C/SC)[C@H](C)[C@@]3(C)[C@H](OC(=O)C(\C)=C/C)C1=C(C)C(=O)O2
InChI Identifier
InChI=1S/C25H34O7S/c1-8-14(2)22(27)31-21-20-15(3)23(28)32-25(20,29-6)13-17-9-10-18(16(4)24(17,21)5)30-19(26)11-12-33-7/h8,11-12,16-18,21H,9-10,13H2,1-7H3/b12-11-,14-8-/t16-,17+,18-,21+,24+,25+/m0/s1
InChI KeyWAJCGTCCWFRXDF-GNUXCKEYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Petasites japonicusLOTUS 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
  • Eremophilanolide or secoeremophilanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Tricarboxylic acid or derivatives
  • Ketal
  • Fatty acid ester
  • 2-furanone
  • Vinylogous thioester
  • Fatty acyl
  • Acrylic acid or derivatives
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Thioenolether
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP5.4ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area88.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.91 m³·mol⁻¹ChemAxon
Polarizability49.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 Compound101942891
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]