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Record Information
Version2.0
Created at2021-06-21 00:22:06 UTC
Updated at2021-06-30 00:18:05 UTC
NP-MRD IDNP0042789
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-angeloyloxy-1-hydroxy-3,4-epoxygermacra-9,11(13)-dien-8,12-olide
Provided ByJEOL DatabaseJEOL Logo
Description 6-angeloyloxy-1-hydroxy-3,4-epoxygermacra-9,11(13)-dien-8,12-olide is found in Eupatorium kiirunense, Eupatorium lindleyanum, Helianthus annuus L.cv.Peredovick , Helianthus tuberosus , Leptocarpha rivularis, Tithonia tagetiflora Desv. (Asteraceae) and Viguiera eriophora ssp.eriophora. 6-angeloyloxy-1-hydroxy-3,4-epoxygermacra-9,11(13)-dien-8,12-olide was first documented in 2013 (Huynh, N. V., et al.).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H26O6
Average Mass362.4220 Da
Monoisotopic Mass362.17294 Da
IUPAC Name(1R,2R,4R,6S,8S,9Z,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1R,2R,4R,6S,8S,9Z,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])[C@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[C@]2(O[C@@]2([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6-,11-7-/t13-,14+,15+,16-,17-,20+/m0/s1
InChI KeyDZTWAOVNNLDWNH-IHGBIZJZSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eupatorium kiirunensePlant
Eupatorium lindleyanumPlant
Helianthus annuus L.cv.PeredovickPlant
Helianthus tuberosusPlant
Leptocarpha rivularisPlant
Tithonia tagetiflora Desv. (Asteraceae)JEOL database
    • Huynh, N. V., et al., Magn. Reson. Chem. 51, 439 (2013)
Viguiera eriophora ssp.eriophoraPlant
Chemical Taxonomy
ClassificationNot classified
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
logP1.45ALOGPS
logP2.41ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.52ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area85.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.54 m³·mol⁻¹ChemAxon
Polarizability37.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General References
  1. Huynh, N. V., et al. (2013). Huynh, N. V., et al., Magn. Reson. Chem. 51, 439 (2013). Mag. Reson. Chem..