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Record Information
Version2.0
Created at2022-09-10 05:34:59 UTC
Updated at2022-09-10 05:35:00 UTC
NP-MRD IDNP0296162
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-{2-[(5s,6as,7r,8s,10as)-5-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]ethyl}-5h-furan-2-one
DescriptionAmphiacrolide L belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 4-{2-[(5s,6as,7r,8s,10as)-5-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]ethyl}-5h-furan-2-one is found in Amphiachyris dracunculoides. 4-{2-[(5s,6as,7r,8s,10as)-5-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]ethyl}-5h-furan-2-one was first documented in 1996 (PMID: 8778236). Based on a literature review very few articles have been published on Amphiacrolide L.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H26O5
Average Mass346.4230 Da
Monoisotopic Mass346.17802 Da
IUPAC Name4-{2-[(5S,6aS,7R,8S,10aS)-5-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]ethyl}-2,5-dihydrofuran-2-one
Traditional Name4-{2-[(5S,6aS,7R,8S,10aS)-5-hydroxy-7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]ethyl}-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@@]23COC(=O)C2=C[C@@H](O)C[C@H]3[C@]1(C)CCC1=CC(=O)OC1
InChI Identifier
InChI=1S/C20H26O5/c1-12-3-6-20-11-25-18(23)15(20)8-14(21)9-16(20)19(12,2)5-4-13-7-17(22)24-10-13/h7-8,12,14,16,21H,3-6,9-11H2,1-2H3/t12-,14+,16-,19+,20+/m0/s1
InChI KeyCIYUVACHWWSUHM-RQWSGRKOSA-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
Amphiachyris dracunculoidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative Parents
Substituents
  • Diterpene lactone
  • Diterpenoid
  • Clerodane diterpenoid
  • Naphthofuran
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Oxolane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Dihydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • 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
logP2.62ChemAxon
pKa (Strongest Acidic)7.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.79 m³·mol⁻¹ChemAxon
Polarizability36.83 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 ID8769065
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10593691
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Harraz FM, Doskotch RW: Cis-clerodane diterpene lactones from Amphiachyris dracunculoides. 3. J Nat Prod. 1996 May;59(5):463-8. doi: 10.1021/np9601263. [PubMed:8778236 ]
  2. LOTUS database [Link]