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Record Information
Version2.0
Created at2022-03-17 20:54:39 UTC
Updated at2026-02-12 00:01:47 UTC
NP-MRD IDNP0048324
Natural Product DOIhttps://doi.org/10.57994/6375
Secondary Accession NumbersNone
Natural Product Identification
Common NameMatairesinol
DescriptionMatairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is found in Abies nephrolepis, Abies pinsapo, Anemone cernua, Arctium lappa, Berberis koreana, Beta vulgaris, Bupleurum salicifolium, Calocedrus formosana, Carthamus tinctorius, Cedrus deodara, Centaurea arenaria, Centaurea aspera, Centaurea calcitrapa, Centaurea melitensis, Centaurea nigra, Centaurea scabiosa, Centaurea scoparia, Centaurea solstitialis, Chiococca alba, Citrus sinensis, Crossosoma bigelovii, Cryptomeria japonica, Daphne feddei, Daphne oleoides, Tetradium glabrifolium, Forsythia intermedia, Forsythia koreana, Forsythia ovata, Forsythia suspensa, Forsythia viridissima, Hordeum vulgare, Ipomoea cairica, Juniperus phoenicea, Himalaiella heteromalla, Linum album, Linum flavum, Oenanthe aquatica, Persea americana, Phoenix dactylifera, Picea glauca, Picea obovata, Pinus armandii, Saussurea medusa, Saussurea salicifolia, Selaginella doederleinii , Stellera chamaejasme, Symplocos setchuensis, Taiwania cryptomerioides, Taxus cuspidata, Taxus mairei, Thuja occidentalis, Thujopsis dolabrata, Trachelospermum asiaticum, Trachelospermum axillare, Tsuga chinensis, Tsuga heterophylla, Vaccinium myrtillus, Vitis vinifera, Zanthoxylum ailanthoides, Zanthoxylum kellermanii and Zanthoxylum schinifolium. Matairesinol was first documented in 2008 (PMID: 18803219). Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 41661373).
Structure
Thumb
Synonyms
ValueSource
4,4'-Dihydroxy-3,3'-dimethoxylignan-9,9'-olideHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone, 9ciHMDB
Dihydro-3,4-divanillyl-2(3H)-furanone, 8ciHMDB
Chemical FormulaC20H22O6
Average Mass358.3851 Da
Monoisotopic Mass358.14164 Da
IUPAC Name3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Name3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC(CC2C(CC3=CC(OC)=C(O)C=C3)COC2=O)=CC=C1O
InChI Identifier
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3
InChI KeyMATGKVZWFZHCLI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies nephrolepisLOTUS Database
Abies pinsapoLOTUS Database
Anemone cernuaLOTUS Database
Arctium lappaLOTUS Database
Berberis koreanaLOTUS Database
Beta vulgarisLOTUS Database
Bupleurum salicifoliumLOTUS Database
Calocedrus formosanaLOTUS Database
Capparis spinosaFooDB
Carthamus tinctoriusLOTUS Database
Cedrus deodaraLOTUS Database
Centaurea arenariaLOTUS Database
Centaurea asperaLOTUS Database
Centaurea calcitrapaLOTUS Database
Centaurea melitensisLOTUS Database
Centaurea nigraLOTUS Database
Centaurea scabiosaLOTUS Database
Centaurea scopariaLOTUS Database
Centaurea solstitialisLOTUS Database
Chiococca albaLOTUS Database
Citrus sinensisLOTUS Database
Crossosoma bigeloviiLOTUS Database
Cryptomeria japonicaLOTUS Database
Daphne feddeiLOTUS Database
Daphne oleoidesLOTUS Database
Euodia fargesiiLOTUS Database
Forsythia intermedia
      Not Available
Forsythia intermediaLOTUS Database
Forsythia koreanaLOTUS Database
Forsythia ovataLOTUS Database
Forsythia suspensaLOTUS Database
Forsythia viridissimaLOTUS Database
Hordeum vulgareLOTUS Database
Ipomoea cairicaLOTUS Database
Juniperus phoeniceaLOTUS Database
Jurinea heteromallaLOTUS Database
Linum albumLOTUS Database
Linum flavumLOTUS Database
Linum usitatissimumFooDB
Oenanthe aquaticaLOTUS Database
Persea americanaLOTUS Database
Phoenix dactyliferaLOTUS Database
Picea glaucaLOTUS Database
Picea obovataLOTUS Database
Pinus armandiiLOTUS Database
Saussurea medusaLOTUS Database
Saussurea salicifoliaLOTUS Database
Secale cerealeFooDB
Selaginella doederleinii-
Sesamum indicumFooDB
Stellera chamaejasmeLOTUS Database
Symplocos setchuensisLOTUS Database
Taiwania cryptomerioidesLOTUS Database
Taxus cuspidataLOTUS Database
Taxus maireiLOTUS Database
Thuja occidentalisLOTUS Database
Thujopsis dolabrataLOTUS Database
Trachelospermum asiaticumLOTUS Database
Trachelospermum axillareLOTUS Database
Tsuga chinensisLOTUS Database
Tsuga heterophyllaLOTUS Database
Vaccinium myrtillusLOTUS Database
Vitis viniferaLOTUS Database
Zanthoxylum ailanthoidesLOTUS Database
Zanthoxylum kellermaniiLOTUS Database
Zanthoxylum schinifoliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP2.79ALOGPS
logP3.29ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.63 m³·mol⁻¹ChemAxon
Polarizability37.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0035789
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014539
KNApSAcK IDNot Available
Chemspider ID306665
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMatairesinol
METLIN IDNot Available
PubChem Compound345761
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800. [PubMed:18803219 ]
  2. Gosavi R, McMurrick P, Nguyen TC, Narasimhan V: Parastomal hernia prevention and repair in Australasia: A binational CSSANZ survey of contemporary practice. Hernia. 2026 Feb 9;30(1):90. doi: 10.1007/s10029-025-03581-8. [PubMed:41661373 ]
  3. DOI: 10.1016/0031-9422(90)85050-p