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Tellimagrandin II (FDB018807)

Record Information
Version1.0
Creation date2010-04-08 22:13:57 UTC
Update date2019-11-26 03:16:43 UTC
Primary IDFDB018807
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTellimagrandin II
DescriptionTellimagrandin II, also known as cornustannin 2 or eugeniin, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Tellimagrandin II is an extremely weak basic (essentially neutral) compound (based on its pKa). Tellimagrandin II is found, on average, in the highest concentration in cloves. Tellimagrandin II has also been detected, but not quantified in, several different foods, such as ostrich ferns, lemon balms, pomegranates, cucumbers, and sorghums. This could make tellimagrandin II a potential biomarker for the consumption of these foods.
CAS Number58970-75-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.19 g/LALOGPS
logP3.32ALOGPS
logP4.26ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.29ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area444.18 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity213.83 m³·mol⁻¹ChemAxon
Polarizability83.68 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC41H30O26
IUPAC name3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-13-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2
InChI KeyJCGHAEBIBSEQAD-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight938.6613
Monoisotopic Molecular Weight938.102531132
Classification
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Pentacarboxylic acid or derivatives
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.46%; H 3.22%; O 44.32%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +10 (c, 0.85 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g4i-0902001302-8ed9d8fb1bc0d0278fd02015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0901000101-7395f2b23933bc99ab8b2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-0952100000-d44b5fbdac0f2ace83392015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0900000503-c9595fe6e3d7e9b886ab2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0902010100-46fc02bcc3ad7c0817942015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0911000000-38d0e5cf8a19459470742015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ri-0200020419-9ed34a94f9a4008505be2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8i-1900010362-c6b92cd030e5a51af58c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-102j-3902042232-07e492047964a4dd4ce42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0600000907-4b9c3a68a2de7cb927802021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-0901010133-7cc0b2600d3c48e0106b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ov-5700011290-38242e0ee54bd6ce7d922021-09-22View Spectrum
NMRNot Available
ChemSpider ID133605
ChEMBL IDNot Available
KEGG Compound IDC10224
Pubchem Compound ID151590
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39265
CRC / DFC (Dictionary of Food Compounds) IDLMS65-D:LMS75-G
EAFUS IDNot Available
Dr. Duke IDTELLIMAGRANDIN-II|TELLIMAGRANDIN|CORNUS-TANNIN-2|EUGENIIN
BIGG IDNot Available
KNApSAcK IDC00002920
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 herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti lipolyticDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.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
topoisomerase-II inhibitor50750 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
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.