(-)-Wikstromol (CHEM024604)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:48:40 UTC
Update Date2016-11-09 01:17:55 UTC
Accession NumberCHEM024604
Identification
Common Name(-)-Wikstromol
ClassSmall Molecule
Description(-)-Wikstromol is found in fruits. (-)-Wikstromol is obtained from Pinus palustris (pitch pine) and Carissa edulis (agam
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass374.385 g/mol
Monoisotopic Mass374.137 g/mol
CAS Registry Number34444-37-6
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
SMILESCOC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0901000000-78e3c7cf8158232e1495Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003r-2031090000-c8fb8418fd6953dad145Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0930000000-fe78dc9c087a79e0d798Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0119000000-2905fe9482c8ec5017efSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0930000000-fe78dc9c087a79e0d798Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0911000000-ec4863cd8d55422e9f76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d553Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d553Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0409000000-eb78288de8a68839bc4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0921000000-357782c3854c3e65ee64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-1a2efb46507e034975e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-419b539150dca3678a6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0229000000-0f88eecb98483341b7f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1669000000-e5efde8fb414170b7337Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030598
FooDB IDFDB002492
Phenol Explorer IDNot Available
KNApSAcK IDC00000599
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID90295
ChEBI ID1007254
PubChem Compound ID99938
Kegg Compound IDC10725
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.