Showing Compound Card for (+)-lariciresinol (CDB000225)

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Record Information
Version1.0
Created at2020-03-19 00:25:28 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000225
Secondary Accession NumbersNot Available
Cannabis Compound 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LariciresinolChEBI
Larici-resinolMeSH
tetrahydro-2-(4-Hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanolMeSH
(+)-LariciresinolPhytoBank
Chemical FormulaC20H24O6
Average Molecular Weight360.4
Monoisotopic Molecular Weight360.1573
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
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
Ontology
Not Available
Physical Properties
StateSolid
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-lariciresinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0119000000-1b51be74b31ac9d7b5392017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03du-0779000000-e7be7d105b100a9c3b9c2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1910000000-b979ee1e05cf5260eb792017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-7a840402d6d204c9b8c72017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-0019000000-ef7220328296c1790e212017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ikl-1926000000-30d6a96496d1ab30c2412017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-bb1d565a494ee8df519a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0967000000-392787799b00541a06442021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-1924000000-af0c5df11ebeae93db352021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-2acd137877feef0611c12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-0009000000-d37a341dfd5a59b2d9ba2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0269000000-23623d625c85715481802021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0303941
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030072
KNApSAcK IDC00000603
Chemspider ID294521
KEGG Compound IDC10646
BioCyc IDCPD-8907
BiGG IDNot Available
Wikipedia LinkLariciresinol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID67246
References
General References
  1. Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. [PubMed:26870049 ]