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Record Information
Version1.0
Created at2022-09-12 07:16:43 UTC
Updated at2022-09-12 07:16:43 UTC
NP-MRD IDNP0326053
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione
DescriptionPlukenetione C belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione is found in Hypericum sampsonii. It was first documented in 2010 (PMID: 20397228). Based on a literature review very few articles have been published on Plukenetione C (PMID: 29461053).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H42O7
Average Mass550.6920 Da
Monoisotopic Mass550.29305 Da
IUPAC Name(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione
Traditional Name(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione
CAS Registry NumberNot Available
SMILES
CC(C)=CC[C@]12C[C@@H]3C[C@@H]4[C@](C[C@@H](OOC4(C)C)C(C)(C)O)(C1=O)C(=O)[C@](C(=O)C1=CC=CC=C1)(C2=O)C3(C)C
InChI Identifier
InChI=1S/C33H42O7/c1-19(2)14-15-31-17-21-16-22-30(7,8)40-39-23(29(5,6)38)18-32(22,25(31)35)27(37)33(26(31)36,28(21,3)4)24(34)20-12-10-9-11-13-20/h9-14,21-23,38H,15-18H2,1-8H3/t21-,22-,23+,31-,32+,33-/m0/s1
InChI KeyXWHHFHMIFCAIHB-BELRDVMKSA-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
Hypericum sampsoniiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Aryl alkyl ketone
  • Benzoyl
  • Dioxepane
  • 1,2-dioxepane
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Dialkyl peroxide
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP6.56ChemAxon
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity150.79 m³·mol⁻¹ChemAxon
Polarizability59.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00046319
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100932396
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yang XW, Grossman RB, Xu G: Research Progress of Polycyclic Polyprenylated Acylphloroglucinols. Chem Rev. 2018 Apr 11;118(7):3508-3558. doi: 10.1021/acs.chemrev.7b00551. Epub 2018 Feb 20. [PubMed:29461053 ]
  2. Xiao ZY, Zeng YH, Mu Q, Shiu WK, Gibbons S: Prenylated benzophenone peroxide derivatives from Hypericum sampsonii. Chem Biodivers. 2010 Apr;7(4):953-8. doi: 10.1002/cbdv.200900247. [PubMed:20397228 ]
  3. LOTUS database [Link]