Showing Compound Card for (+)-Pinoresinol (CDB000226)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:25:31 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000226
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-Pinoresinol
Description(+)-Pinoresinol or pinoresinol, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Pinoresinol is a naturally occurring lignan found in several different plant species, such as Styrax sp., Forsythia suspensa and in Cannabis sativa (PMID: 26870049 ). Pinoresinol is also found in sesame seeds, in brassica vegetables and in olive oil. Pinoresinol, along with other plant lignans, are converted into enterolignans by intestinal microflora in the human body (PMID:15877880 ). It has also been found in the caterpillar of the cabbage butterfly, Pieris rapae, where it serves as a defence against ants (PMID: 17030818 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,4'-(1S,3AR,4S,6ar)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2-methoxyphenol)ChEBI
PinoresinolChEBI
Pino-resinolMeSH
(+)-PinoresinolPhytoBank
d-PinoresinolPhytoBank
Chemical FormulaC20H22O6
Average Molecular Weight358.39
Monoisotopic Molecular Weight358.1416
IUPAC Name4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol
Traditional Namepinoresinol
CAS Registry Number487-36-5
SMILES
COC1=C(O)C=CC(=C1)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
InChI KeyHGXBRUKMWQGOIE-AFHBHXEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative Parents
Substituents
  • Furanoid lignan
  • Furofuran lignan skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Furofuran
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.31ALOGPS
logP2.28ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.38 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.1 m³·mol⁻¹ChemAxon
Polarizability36.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-Pinoresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Pinoresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-002r-0910000000-3da0fadda172e5879cbe2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0a4i-0109000000-ae55894f254d847b14022020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0a4i-0209000000-bbbfa93613cdffd1ac782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0pb9-0509000000-c23f0cad60eece30bf6f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0zfr-0908000000-ac5466a0e7c9edfa9cc12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-0udi-0902000000-5f3ce91eda6aa1d04a8b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0udi-0900000000-7d5f755188ca3f19faf62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0udr-0900000000-ccf8341709117b16d5502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-0f79-0900000000-ef16dd54c95a115662922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-000i-0900000000-cf3b97de0a7d237386502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-000i-0900000000-10337716d11f91d3b09a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-0udi-0901000000-3816e060375c0e5447662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-0006-9100000000-8bc7a6bcc89f3738c20f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-000i-0900000000-8af34ec8bd25d55ab53f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-004j-0930000000-f70d459e782678cc81772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-03dj-0900000000-50a42cdbe635b50fbb882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-004i-0911000000-bfd08db5f4762b72c55d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 25V, negativesplash10-0a4i-0900000000-ff24654a4c917d8dfcbb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-000i-0900000000-02f006006944f634f8702020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-c344714f00e3f14bb89a2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0059000000-c3f4270fe98bd82c80f02019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7900000000-b3541c444a60d88270a52019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-0f92b23fa1d7807897e82019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0119000000-f3bc9f51a011db2f02ef2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1933000000-523f9adcba04bcb6b7c62019-02-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007190
Chemspider ID66116
KEGG Compound IDC05366
BioCyc IDCPD-8905
BiGG IDNot Available
Wikipedia LinkPinoresinol
METLIN IDNot Available
PubChem Compound73399
PDB IDNot Available
ChEBI ID40
References
General References
  1. Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr. 2005 Mar;93(3):393-402. doi: 10.1079/bjn20051371. [PubMed:15877880 ]
  2. 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 ]
  3. Schroeder FC, del Campo ML, Grant JB, Weibel DB, Smedley SR, Bolton KL, Meinwald J, Eisner T: Pinoresinol: A lignol of plant origin serving for defense in a caterpillar. Proc Natl Acad Sci U S A. 2006 Oct 17;103(42):15497-501. doi: 10.1073/pnas.0605921103. Epub 2006 Oct 9. [PubMed:17030818 ]