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Record Information
Version2.0
Created at2022-09-09 05:55:16 UTC
Updated at2022-09-09 05:55:16 UTC
NP-MRD IDNP0280243
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,7s,8r)-8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0²,⁶]undec-5-en-7-ol
DescriptionOrientalol F belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,2r,7s,8r)-8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0²,⁶]undec-5-en-7-ol is found in Alisma plantago-aquatica. (1r,2r,7s,8r)-8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0²,⁶]undec-5-en-7-ol was first documented in 2003 (PMID: 12895533). Based on a literature review a small amount of articles have been published on Orientalol F (PMID: 24175907) (PMID: 32052978) (PMID: 20024217).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H24O2
Average Mass236.3550 Da
Monoisotopic Mass236.17763 Da
IUPAC Name(1R,2R,7S,8R)-1,5-dimethyl-8-(propan-2-yl)-11-oxatricyclo[6.2.1.0^{2,6}]undec-5-en-7-ol
Traditional Name(1R,2R,7S,8R)-8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0^{2,6}]undec-5-en-7-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@@]12CC[C@@](C)(O1)[C@@H]1CCC(C)=C1[C@@H]2O
InChI Identifier
InChI=1S/C15H24O2/c1-9(2)15-8-7-14(4,17-15)11-6-5-10(3)12(11)13(15)16/h9,11,13,16H,5-8H2,1-4H3/t11-,13+,14-,15-/m1/s1
InChI KeyOPAPNRSNRRMTSU-FAAHXZRKSA-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
Alisma plantago-aquaticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP2.5ChemAxon
pKa (Strongest Acidic)13.41ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.47 m³·mol⁻¹ChemAxon
Polarizability27.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00037586
Chemspider ID9196068
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11020886
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Obradors C, Echavarren AM: Gold-catalyzed rearrangements and beyond. Acc Chem Res. 2014 Mar 18;47(3):902-12. doi: 10.1021/ar400174p. Epub 2013 Oct 31. [PubMed:24175907 ]
  2. Mou SB, Xiao W, Wang HQ, Wang SJ, Xiang Z: Syntheses of Epoxyguaiane Sesquiterpenes (-)-Englerin A, (-)-Oxyphyllol, (+)-Orientalol E, and (+)-Orientalol F: A Synthetic Biology Approach. Org Lett. 2020 Mar 6;22(5):1976-1979. doi: 10.1021/acs.orglett.0c00325. Epub 2020 Feb 13. [PubMed:32052978 ]
  3. Jimenez-Nunez E, Molawi K, Echavarren AM: Stereoselective gold-catalyzed cycloaddition of functionalized ketoenynes: synthesis of (+)-orientalol F. Chem Commun (Camb). 2009 Dec 21;(47):7327-9. doi: 10.1039/b920119j. Epub 2009 Nov 5. [PubMed:20024217 ]
  4. Peng GP, Tian G, Huang XF, Lou FC: Guaiane-type sesquiterpenoids from Alisma orientalis. Phytochemistry. 2003 Aug;63(8):877-81. doi: 10.1016/s0031-9422(03)00222-x. [PubMed:12895533 ]
  5. LOTUS database [Link]