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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:52 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030598
Secondary Accession Numbers
  • HMDB30598
Metabolite Identification
Common Name(-)-Wikstromol
Description(-)-Wikstromol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-Wikstromol is found, on average, in the highest concentration within sesames (Sesamum orientale) (-)-Wikstromol has also been detected, but not quantified in, fruits. This could make (-)-wikstromol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (-)-Wikstromol.
Structure
Data?1563862010
Synonyms
ValueSource
(+)-NortrachelogeninHMDB
(-)-NortrachelogeninHMDB
arbo 6HMDB
DibenzylbutyrolactoneHMDB
NortrachelogeninHMDB, MeSH
WikstromolHMDB, MeSH
Nortrachelogenin, (3R-cis)-isomerMeSH
Dihydro-3-hydroxy-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-2(3H)-furanoneMeSH
8'-(R)-4,4',8-Trihydroxy-3,3'-dimethoxylignanolideMeSH
Chemical FormulaC20H22O7
Average Molecular Weight374.3845
Monoisotopic Molecular Weight374.136553058
IUPAC Name3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Name3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
CAS Registry Number34444-37-6
SMILES
COC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3
InChI KeyZITBJWXLODLDRH-UHFFFAOYSA-N
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
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point609.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2515 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.920 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP1.88ALOGPS
logP2.43ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.09 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.21931661259
DarkChem[M-H]-189.89431661259
DeepCCS[M+H]+193.91630932474
DeepCCS[M-H]-191.55830932474
DeepCCS[M-2H]-225.68230932474
DeepCCS[M+Na]+200.96930932474
AllCCS[M+H]+189.632859911
AllCCS[M+H-H2O]+186.532859911
AllCCS[M+NH4]+192.432859911
AllCCS[M+Na]+193.232859911
AllCCS[M-H]-191.332859911
AllCCS[M+Na-2H]-191.532859911
AllCCS[M+HCOO]-191.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-WikstromolCOC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C15250.9Standard polar33892256
(-)-WikstromolCOC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C13251.2Standard non polar33892256
(-)-WikstromolCOC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C13239.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Wikstromol,1TMS,isomer #1COC1=CC(CC2(O)C(=O)OCC2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3245.1Semi standard non polar33892256
(-)-Wikstromol,1TMS,isomer #2COC1=CC(CC2COC(=O)C2(CC2=CC=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O3218.5Semi standard non polar33892256
(-)-Wikstromol,1TMS,isomer #3COC1=CC(CC2COC(=O)C2(O)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3229.9Semi standard non polar33892256
(-)-Wikstromol,2TMS,isomer #1COC1=CC(CC2(O[Si](C)(C)C)C(=O)OCC2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3225.8Semi standard non polar33892256
(-)-Wikstromol,2TMS,isomer #2COC1=CC(CC2COC(=O)C2(O)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C3230.3Semi standard non polar33892256
(-)-Wikstromol,2TMS,isomer #3COC1=CC(CC2COC(=O)C2(CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O3208.0Semi standard non polar33892256
(-)-Wikstromol,3TMS,isomer #1COC1=CC(CC2COC(=O)C2(CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3214.7Semi standard non polar33892256
(-)-Wikstromol,1TBDMS,isomer #1COC1=CC(CC2(O)C(=O)OCC2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3500.3Semi standard non polar33892256
(-)-Wikstromol,1TBDMS,isomer #2COC1=CC(CC2COC(=O)C2(CC2=CC=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O3517.7Semi standard non polar33892256
(-)-Wikstromol,1TBDMS,isomer #3COC1=CC(CC2COC(=O)C2(O)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3485.8Semi standard non polar33892256
(-)-Wikstromol,2TBDMS,isomer #1COC1=CC(CC2(O[Si](C)(C)C(C)(C)C)C(=O)OCC2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3749.4Semi standard non polar33892256
(-)-Wikstromol,2TBDMS,isomer #2COC1=CC(CC2COC(=O)C2(O)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3730.6Semi standard non polar33892256
(-)-Wikstromol,2TBDMS,isomer #3COC1=CC(CC2COC(=O)C2(CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O3725.8Semi standard non polar33892256
(-)-Wikstromol,3TBDMS,isomer #1COC1=CC(CC2COC(=O)C2(CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3951.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Wikstromol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0901000000-78e3c7cf8158232e14952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Wikstromol GC-MS (3 TMS) - 70eV, Positivesplash10-003r-2031090000-c8fb8418fd6953dad1452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Wikstromol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Wikstromol , negative-QTOFsplash10-00di-0119000000-2905fe9482c8ec5017ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Wikstromol LC-ESI-qTof , Positive-QTOFsplash10-000i-0930000000-fe78dc9c087a79e0d7982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Wikstromol , positive-QTOFsplash10-000i-0930000000-fe78dc9c087a79e0d7982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Wikstromol , positive-QTOFsplash10-000i-0911000000-ec4863cd8d55422e9f762017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Negative-QTOFsplash10-00dr-0079000000-9d1e94ab28622937cec52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Negative-QTOFsplash10-0079-0469000000-5e6c162ac7baf304061d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Negative-QTOFsplash10-0ads-0954000000-b7b2e200baf1fb72d5532015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Negative-QTOFsplash10-00dr-0079000000-9d1e94ab28622937cec52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Negative-QTOFsplash10-0079-0469000000-5e6c162ac7baf304061d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Negative-QTOFsplash10-0ads-0954000000-b7b2e200baf1fb72d5532015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Negative-QTOFsplash10-00di-0019000000-419b539150dca3678a6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Negative-QTOFsplash10-00di-0229000000-0f88eecb98483341b7f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Negative-QTOFsplash10-00di-1669000000-e5efde8fb414170b73372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Positive-QTOFsplash10-004i-0319000000-dd9ef3e03c550e5f0ef22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Positive-QTOFsplash10-000i-0946000000-6564c7dba5c7dc863e642015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Positive-QTOFsplash10-01p9-1900000000-f69fe05a373b7d4b49cf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Positive-QTOFsplash10-004i-0319000000-dd9ef3e03c550e5f0ef22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Positive-QTOFsplash10-000i-0946000000-6564c7dba5c7dc863e642015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Positive-QTOFsplash10-01p9-1900000000-f69fe05a373b7d4b49cf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 10V, Positive-QTOFsplash10-004i-0409000000-eb78288de8a68839bc4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 20V, Positive-QTOFsplash10-0a4r-0921000000-357782c3854c3e65ee642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Wikstromol 40V, Positive-QTOFsplash10-000i-1920000000-1a2efb46507e034975e72021-09-22Wishart 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 IDFDB002492
KNApSAcK IDC00000599
Chemspider ID90295
KEGG Compound IDC10725
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound99938
PDB IDNot Available
ChEBI ID1007254
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1486851
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hu K, Kobayashi H, Dong A, Iwasaki S, Yao X: Antifungal, antimitotic and anti-HIV-1 agents from the roots of Wikstroemia indica. Planta Med. 2000 Aug;66(6):564-7. [PubMed:10985087 ]
  2. Ji-Xian G, Handa SS, Pezzuto JM, Kinghorn AD, Farnsworth NR: Plant Anticancer Agents XXXIII. Constituents of Passerina vulgaris1. Planta Med. 1984 Jun;50(3):264-5. [PubMed:17340308 ]
  3. Kato A, Hashimoto Y, Kidokoro M: (+)-Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica. J Nat Prod. 1979 Mar-Apr;42(2):159-62. [PubMed:501363 ]
  4. Lee KH, Tagahara K, Suzuki H, Wu RY, Haruna M, Hall IH, Huang HC, Ito K, Iida T, Lai JS: Antitumor agents. 49 tricin, kaempferol-3-O-beta-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles from Wikstroemia indica. J Nat Prod. 1981 Sep-Oct;44(5):530-5. [PubMed:7320737 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .