Hmdb loader
Show more...Show more...Show more...
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
Thumb
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
Predicted Chromatographic Properties
Spectra
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.. .