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Showing Compound Trachelogenin (FDB020276)

Record Information
Version1.0
Creation date2010-04-08 22:14:55 UTC
Update date2025-11-19 02:29:16 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
MOLSDFPDBSMILESInChI
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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
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
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0519000000-1014d5320482c475be952019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0924000000-d6eced9520b64982b5972019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-2901000000-da8c42bb7e0b206e92d92019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0069000000-66299dd4a05ea7d2b6942019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0449000000-5f524d23f8e4a3e9c3f42019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02g7-0659000000-956f0981807b4de1534b2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-86491115644010258ccd2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0933000000-7e11a408dd9a1b1a3d832021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-3958000000-00e44846a35cf59c83be2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-2c73c7ca58264e177ca32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0933000000-ab4cca7d5a9a4a6362572021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-4923000000-d4a6151a3c862b2d9e102021-10-21View Spectrum
NMRNot Available
ChemSpider ID437574
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
Food Biomarker OntologyNot Available
VMH 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 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti hypertensive52217 An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health.DUKE
Anti-integrase23924 An agent that blocks the activity of integrase, an enzyme essential for HIV replication, reducing viral integration into host DNA. Therapeutically, it's used to treat HIV infection, preventing the virus from replicating and slowing disease progression, commonly used in combination with other antiretroviral therapies.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-lymphomicAn agent that targets and destroys lymphatic cells that form tumors, playing a crucial role in cancer treatment. Therapeutically, it is used to manage lymphomas, with key medical applications in chemotherapy and immunotherapy to combat blood cell cancers.DUKE
Anti topoisomerase-II50750 An agent that inhibits topoisomerase-II, an enzyme involved in DNA replication. Therapeutically, it's used in cancer treatment, particularly in leukemia and lymphoma, to prevent DNA replication and induce cell death. Key medical uses include chemotherapy for various cancers, exploiting its ability to disrupt DNA processes and halt tumor growth.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cardiac38070 Relating to the heart, referring to agents or functions that support heart health, treat cardiovascular diseases, or regulate heart rhythm, commonly used in managing conditions such as arrhythmias, heart failure, and hypertension.DUKE
CytostaticAn agent that inhibits cell growth, playing a biological role in regulating cell proliferation. Therapeutically, it is used to slow or stop the growth of abnormal cells. Key medical uses include cancer treatment, where it helps prevent tumor growth, and in managing conditions like psoriasis and rheumatoid arthritis.DUKE
HIV-reverse-transcriptase inhibitor23924 An agent that blocks the activity of reverse transcriptase, an enzyme essential for HIV replication, reducing viral load and slowing disease progression. Therapeutically, it is used to treat HIV/AIDS, often in combination with other antiretroviral medications to prevent drug resistance and manage symptoms.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase inhibitor23924 An agent that blocks the activity of topoisomerase enzymes, which unwind DNA during replication. Therapeutically, it prevents cancer cell growth, commonly used in managing various types of cancer, including leukemia, lymphoma, and solid tumors.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.