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Record Information
Version1.0
Created at2022-09-12 16:30:49 UTC
Updated at2022-09-12 16:30:49 UTC
NP-MRD IDNP0330801
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraen-1-yl acetate
DescriptionEleganolone acetate belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. (2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraen-1-yl acetate is found in Cystoseira brachycarpa. It was first documented in 1998 (PMID: 9548834). Based on a literature review very few articles have been published on eleganolone acetate.
Structure
Thumb
Synonyms
ValueSource
Eleganolone acetic acidGenerator
Chemical FormulaC22H34O3
Average Mass346.5110 Da
Monoisotopic Mass346.25079 Da
IUPAC Name(2E,6E,10E)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraen-1-yl acetate
Traditional Name(2E,6E,10E)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraen-1-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C)=CC(=O)C\C(C)=C\CC\C(C)=C\CC\C(C)=C\COC(C)=O
InChI Identifier
InChI=1S/C22H34O3/c1-17(2)15-22(24)16-20(5)12-8-10-18(3)9-7-11-19(4)13-14-25-21(6)23/h9,12-13,15H,7-8,10-11,14,16H2,1-6H3/b18-9+,19-13+,20-12+
InChI KeyXLRINIVOESDDOA-QGBQGRNXSA-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
Cystoseira brachycarpaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Fatty alcohol ester
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP5.44ChemAxon
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity108.56 m³·mol⁻¹ChemAxon
Polarizability42.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
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 ID10344492
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23242742
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li J, Lan J, Liu Z, Li Y: Studies on the Synthesis of Elegan-Type Linear Diterpenes: The Efficient Total Syntheses of Eleganolone, Eleganolone Acetate, Elegandiol, Eleganonal, and Epoxyeleganolone J Nat Prod. 1998 Jan 23;61(1):92-5. doi: 10.1021/np970227g. [PubMed:9548834 ]
  2. LOTUS database [Link]