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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:59:32 UTC
Update Date2022-03-07 02:53:39 UTC
HMDB IDHMDB0033279
Secondary Accession Numbers
  • HMDB33279
Metabolite Identification
Common Name8-Hydroxypinoresinol
Description8-Hydroxypinoresinol 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. Based on a literature review a significant number of articles have been published on 8-Hydroxypinoresinol.
Structure
Data?1601266285
Synonyms
ValueSource
(+)-1-HydroxypinoresinolHMDB
(+)-8-HydroxypinoresinolHMDB
1alpha-HydroxypinoresinolHMDB
1Α-hydroxypinoresinolHMDB
8alpha-HydroxypinoresinolHMDB
8Α-hydroxypinoresinolHMDB
8-HydroxypinoresinolPhytoBank
Chemical FormulaC20H22O7
Average Molecular Weight374.389
Monoisotopic Molecular Weight374.136553048
IUPAC Name(1S,3aS,4R,6aR)-1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-ol
Traditional Name(1S,3aS,4R,6aR)-1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-ol
CAS Registry Number81426-17-7
SMILES
[H][C@]12CO[C@H](C3=CC=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C1
InChI Identifier
InChI=1S/C20H22O7/c1-24-16-7-11(3-5-14(16)21)18-13-9-26-19(20(13,23)10-27-18)12-4-6-15(22)17(8-12)25-2/h3-8,13,18-19,21-23H,9-10H2,1-2H3/t13-,18-,19-,20-/m1/s1
InChI KeyCICMVLOHBZPXIT-WNISUXOKSA-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
  • Anisole
  • Phenoxy compound
  • Furofuran
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Oxolane
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5160 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.8ALOGPS
logP1.73ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area97.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.98 m³·mol⁻¹ChemAxon
Polarizability37.57 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-219.42230932474
DeepCCS[M+Na]+195.33330932474
AllCCS[M+H]+188.832859911
AllCCS[M+H-H2O]+186.132859911
AllCCS[M+NH4]+191.232859911
AllCCS[M+Na]+191.932859911
AllCCS[M-H]-186.732859911
AllCCS[M+Na-2H]-186.632859911
AllCCS[M+HCOO]-186.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Hydroxypinoresinol[H][C@]12CO[C@H](C3=CC=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C15149.8Standard polar33892256
8-Hydroxypinoresinol[H][C@]12CO[C@H](C3=CC=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C13107.8Standard non polar33892256
8-Hydroxypinoresinol[H][C@]12CO[C@H](C3=CC=C(O)C(OC)=C3)[C@@]1(O)CO[C@@H]2C1=CC=C(O)C(OC)=C13337.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxypinoresinol,1TMS,isomer #1COC1=CC([C@H]2OC[C@]3(O)[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O3261.8Semi standard non polar33892256
8-Hydroxypinoresinol,1TMS,isomer #2COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C)[C@@H](C4=CC=C(O)C(OC)=C4)OC[C@H]23)=CC=C1O3229.5Semi standard non polar33892256
8-Hydroxypinoresinol,1TMS,isomer #3COC1=CC([C@H]2OC[C@@H]3[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@]23O)=CC=C1O3255.3Semi standard non polar33892256
8-Hydroxypinoresinol,2TMS,isomer #1COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C)[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O3195.2Semi standard non polar33892256
8-Hydroxypinoresinol,2TMS,isomer #2COC1=CC([C@H]2OC[C@]3(O)[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O[Si](C)(C)C3241.2Semi standard non polar33892256
8-Hydroxypinoresinol,2TMS,isomer #3COC1=CC([C@H]2OC[C@@H]3[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@]23O[Si](C)(C)C)=CC=C1O3190.9Semi standard non polar33892256
8-Hydroxypinoresinol,3TMS,isomer #1COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C)[C@@H](C4=CC=C(O[Si](C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O[Si](C)(C)C3224.8Semi standard non polar33892256
8-Hydroxypinoresinol,1TBDMS,isomer #1COC1=CC([C@H]2OC[C@]3(O)[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O3523.7Semi standard non polar33892256
8-Hydroxypinoresinol,1TBDMS,isomer #2COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C(C)(C)C)[C@@H](C4=CC=C(O)C(OC)=C4)OC[C@H]23)=CC=C1O3523.4Semi standard non polar33892256
8-Hydroxypinoresinol,1TBDMS,isomer #3COC1=CC([C@H]2OC[C@@H]3[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@]23O)=CC=C1O3518.9Semi standard non polar33892256
8-Hydroxypinoresinol,2TBDMS,isomer #1COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C(C)(C)C)[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O3721.2Semi standard non polar33892256
8-Hydroxypinoresinol,2TBDMS,isomer #2COC1=CC([C@H]2OC[C@]3(O)[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O[Si](C)(C)C(C)(C)C3730.2Semi standard non polar33892256
8-Hydroxypinoresinol,2TBDMS,isomer #3COC1=CC([C@H]2OC[C@@H]3[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@]23O[Si](C)(C)C(C)(C)C)=CC=C1O3718.4Semi standard non polar33892256
8-Hydroxypinoresinol,3TBDMS,isomer #1COC1=CC([C@H]2OC[C@]3(O[Si](C)(C)C(C)(C)C)[C@@H](C4=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OC[C@H]23)=CC=C1O[Si](C)(C)C(C)(C)C3900.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxypinoresinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxypinoresinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 10V, Negative-QTOFsplash10-00di-0009000000-239efcb6359f1ed8086f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 20V, Negative-QTOFsplash10-00du-0169000000-1e180a9db8a31cb5cf8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 40V, Negative-QTOFsplash10-059i-2594000000-e6a0722ab8956a49d6bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 10V, Positive-QTOFsplash10-004i-0009000000-652f1b29f51de119ded92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 20V, Positive-QTOFsplash10-002r-0849000000-aff8bb0e9a04c60efee92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxypinoresinol 40V, Positive-QTOFsplash10-0f79-3985000000-571ce71131a136067cc92021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00007191
Chemspider ID2280027
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3010930
PDB IDNot Available
ChEBI ID175806
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1834431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .