Np mrd loader

Record Information
Version2.0
Created at2022-03-10 18:51:27 UTC
Updated at2022-03-10 22:16:25 UTC
NP-MRD IDNP0044938
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-lariciresinol
Description(+)-Lariciresinol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba) and in Cannabis sativa plants (PMID: 26870049 ).
Structure
Thumb
Synonyms
ValueSource
LariciresinolChEBI
Larici-resinolMeSH
Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanolMeSH
(+)-LariciresinolPhytoBank
Chemical FormulaC20H24O6
Average Mass360.4010 Da
Monoisotopic Mass360.15729 Da
IUPAC Name4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
Traditional Namelariciresinol
CAS Registry Number27003-73-2
SMILES
COC1=C(O)C=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
InChI KeyMHXCIKYXNYCMHY-AUSJPIAWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies pinsapoLOTUS Database
Actinidia chinensisFooDB
Allium sativumFooDB
Anacardium occidentaleFooDB
Ananas comosusLOTUS Database
Anastatica hierochunticaLOTUS Database
Apis ceranaLOTUS Database
Aquilaria sinensisLOTUS Database
Arabidopsis thalianaLOTUS Database
Araucaria angustifoliaPlant
Arctium lappaPlant
Arum italicumLOTUS Database
Astragalus mongholicusLOTUS Database
Balanophora abbreviata B1Plant
Berberis koreanaLOTUS Database
Brassica fruticulosaLOTUS Database
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. italicaFooDB
Callicarpa furfuraceaLOTUS Database
Camellia sinensisLOTUS Database
Cannabis sativaNULL
      Not Available
Cedrus deodaraLOTUS Database
Citrus paradisiFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cucumis sativus L.FooDB
Cycas revolutaLOTUS Database
Daphne feddeiLOTUS Database
Daphne mezereumLOTUS Database
Daphne odoraPlant
Daphne oleoidesLOTUS Database
Daphne tanguticaPlant
Daucus carota ssp. sativusFooDB
Dipteryx odorataPlant
Dirca occidentalisPlant
Enterococcus faecalisLOTUS Database
Ephedra viridisLOTUS Database
Euterpe oleraceaLOTUS Database
Fagraea racemosaLOTUS Database
Forsythia intermediaLOTUS Database
Fragaria x ananassaFooDB
Gliricidia sepiumLOTUS Database
Gnetum montanumLOTUS Database
Helianthus annuusLOTUS Database
Helianthus annuus L.FooDB
Hemerocallis fulvaLOTUS Database
Hibiscus cannabinusLOTUS Database
Juglans regiaLOTUS Database
Justicia diffusaLOTUS Database
Larix deciduaPlant
Leitneria floridanaLOTUS Database
Linum albumLOTUS Database
Linum usitatissimumFooDB
Magnolia denudataLOTUS Database
Magnolia kachirachiraiLOTUS Database
Malus pumilaLOTUS Database
Morina chinensisLOTUS Database
Nierembergia aristataLOTUS Database
Picea jezoensisLOTUS Database
Prosopis juliflora (Sw.) DC.Plant
Prunus armeniacaFooDB
Pyrus communisFooDB
Rhodiola roseaLOTUS Database
Ribes nigrumLOTUS Database
Rubia yunnanensisLOTUS Database
Sambucus nigraLOTUS Database
Saussurea medusaLOTUS Database
Sesamum indicumFooDB
Solanum lycopersicumFooDB
Solanum tuberosumFooDB
Stellera chamaejasmeLOTUS Database
Styrax camporumLOTUS Database
Taxus cuspidataLOTUS Database
Taxus maireiLOTUS Database
Taxus wallichianaLOTUS Database
Thuja plicataPlant
Tsuga heterophyllaLOTUS Database
Vitex trifoliaLOTUS Database
VitisFooDB
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct Parent7,9'-epoxylignans
Alternative Parents
Substituents
  • 7,9p-epoxylignan
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP2.16ALOGPS
logP2.31ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.38 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.19 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030072
KNApSAcK IDC00000602
Chemspider IDNot Available
KEGG Compound IDC10646
BioCyc IDCPD-8907
BiGG IDNot Available
Wikipedia LinkLariciresinol
METLIN IDNot Available
PubChem Compound332427
PDB IDNot Available
ChEBI ID67246
Good Scents IDNot Available
References
General References
  1. Hwang B, Cho J, Hwang IS, Jin HG, Woo ER, Lee DG: Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans. Biochem Biophys Res Commun. 2011 Jul 8;410(3):489-93. doi: 10.1016/j.bbrc.2011.06.004. Epub 2011 Jun 7. [PubMed:21679690 ]
  2. Esmaeilzadeh Bahabadi S, Sharifi M, Behmanesh M, Safaie N, Murata J, Araki R, Yamagaki T, Satake H: Time-course changes in fungal elicitor-induced lignan synthesis and expression of the relevant genes in cell cultures of Linum album. J Plant Physiol. 2012 Mar 15;169(5):487-91. doi: 10.1016/j.jplph.2011.12.006. Epub 2012 Jan 3. [PubMed:22218086 ]
  3. Chu A, Dinkova A, Davin LB, Bedgar DL, Lewis NG: Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia. J Biol Chem. 1993 Dec 25;268(36):27026-33. [PubMed:8262939 ]