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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:52 UTC
Update Date2019-07-23 06:06:50 UTC
HMDB IDHMDB0030598
Secondary Accession Numbers
  • HMDB30598
Metabolite Identification
Common Name(-)-Wikstromol
Description(-)-Wikstromol is found in fruits. (-)-Wikstromol is obtained from Pinus palustris (pitch pine) and Carissa edulis (agam
Structure
Data?1563862010
Synonyms
ValueSource
(+)-NortrachelogeninHMDB
(-)-NortrachelogeninHMDB
arbo 6HMDB
DibenzylbutyrolactoneHMDB
NortrachelogeninHMDB
WikstromolHMDB
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
DescriptionThis compound 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
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Gamma butyrolactone
  • Saccharide
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0901000000-78e3c7cf8158232e1495JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003r-2031090000-c8fb8418fd6953dad145JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0930000000-fe78dc9c087a79e0d798JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0119000000-2905fe9482c8ec5017efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0930000000-fe78dc9c087a79e0d798JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0911000000-ec4863cd8d55422e9f76JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e64JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0319000000-dd9ef3e03c550e5f0ef2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0946000000-6564c7dba5c7dc863e64JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-f69fe05a373b7d4b49cfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d553JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0079000000-9d1e94ab28622937cec5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0469000000-5e6c162ac7baf304061dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ads-0954000000-b7b2e200baf1fb72d553JSpectraViewer | MoNA
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
FoodDB 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
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.. .