Record Information
Version1.0
Creation date2010-04-08 22:14:55 UTC
Update date2018-01-25 19:43:51 UTC
Primary IDFDB020276
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTrachelogenin
DescriptionTrachelogenin is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Trachelogenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Trachelogenin can be found in burdock and grape wine, which makes trachelogenin a potential biomarker for the consumption of these food products.
CAS Number34209-69-3
Structure
Thumb
Synonyms
SynonymSource
(-)-Trachelogeninbiospider
2(3H)-Furanone, dihydro-3-hydroxy-3-vanillyl-4-veratryl-biospider
Trachelogenindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP2.6ALOGPS
logP2.58ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity101.57 m³·mol⁻¹ChemAxon
Polarizability39.65 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H24O7
IUPAC name4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3
InChI KeyYFVZKLQNMNKWSB-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC2(O)C(CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC=C1O
Average Molecular Weight388.4111
Monoisotopic Molecular Weight388.152203122
Classification
DescriptionThis compound belongs to the class of chemical entities known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLignans, neolignans and related compounds
Sub ClassFuranoid lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Methoxyphenol
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 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
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.94%; H 6.23%; O 28.83%DFC
Melting PointMp 139-141°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -43.5 (c, 0.25 in EtOH)DFC
Spectroscopic UV Data280 (e 4700) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10891
Pubchem Compound ID452855
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID601
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDMBB20-R:MNC00-W
EAFUS IDNot Available
Dr. Duke IDTRACHELOGENIN
BIGG IDNot Available
KNApSAcK IDC00000600
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti integrase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lymphomicDUKE
anti topoisomerase-II50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cardiac38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cytostaticDUKE
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
popoisomerase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.