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Record Information
Version2.0
Created at2021-06-20 22:26:43 UTC
Updated at2021-06-30 00:14:00 UTC
NP-MRD IDNP0040223
Secondary Accession NumbersNone
Natural Product Identification
Common Name10betaH-6beta-acetoxy-7alpha,11alpha-epoxyeremophilan-8-one
Provided ByJEOL DatabaseJEOL Logo
DescriptionAcetic acid (2R)-3-oxo-3',3',8alpha,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1alpha-yl ester belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). 10betaH-6beta-acetoxy-7alpha,11alpha-epoxyeremophilan-8-one is found in Ligularia lamarum and Ligularia subspicata. 10betaH-6beta-acetoxy-7alpha,11alpha-epoxyeremophilan-8-one was first documented in 2011 (Saito, Y., et al.). Based on a literature review very few articles have been published on Acetic acid (2R)-3-oxo-3',3',8alpha,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1alpha-yl ester.
Structure
Thumb
Synonyms
ValueSource
Acetate (2R)-3-oxo-3',3',8a,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1a-yl esterGenerator
Acetate (2R)-3-oxo-3',3',8alpha,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1alpha-yl esterGenerator
Acetate (2R)-3-oxo-3',3',8α,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1α-yl esterGenerator
Acetic acid (2R)-3-oxo-3',3',8a,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1a-yl esterGenerator
Acetic acid (2R)-3-oxo-3',3',8α,8aalpha-tetramethyl-3,4,4aalpha,5,6,7,8,8a-octahydrospiro[naphthalene-2(1H),2'-oxirane]-1α-yl esterGenerator
Chemical FormulaC17H26O4
Average Mass294.3910 Da
Monoisotopic Mass294.18311 Da
IUPAC Name(1S,2R,4aR,8S,8aR)-3',3',8,8a-tetramethyl-3-oxo-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl acetate
Traditional Name(1S,2R,4aR,8S,8aR)-3',3',8,8a-tetramethyl-3-oxo-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl acetate
CAS Registry NumberNot Available
SMILES
[H]C([H])([H])C(=O)O[C@]1([H])[C@]2(OC2(C([H])([H])[H])C([H])([H])[H])C(=O)C([H])([H])[C@@]2([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H]
InChI Identifier
InChI=1S/C17H26O4/c1-10-7-6-8-12-9-13(19)17(15(3,4)21-17)14(16(10,12)5)20-11(2)18/h10,12,14H,6-9H2,1-5H3/t10-,12+,14-,16+,17+/m0/s1
InChI KeyDPWOQVYZNDXRAN-OEWFIBSQSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ligularia lamarumJEOL database
    • Saito, Y., et al, Tetrahedron 67, 2220 (2011).
Ligularia subspicataJEOL database
    • Saito, Y., et al, Tetrahedron 67, 2220 (2011).
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP3.3ALOGPS
logP2.97ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)17.96ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.42 m³·mol⁻¹ChemAxon
Polarizability31.9 ųChemAxon
Number of Rings3ChemAxon
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 Compound101780471
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Saito, Y., et al. (2011). Saito, Y., et al, Tetrahedron 67, 2220 (2011).. Tetrahedron.