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Showing Compound Tellimagrandin I (FDB018804)

Record Information
Version1.0
Creation date2010-04-08 22:13:56 UTC
Update date2020-02-24 19:11:09 UTC
Primary IDFDB018804
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTellimagrandin I
Description3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins 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) 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. 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate can be found in a number of food items such as cloves, rose hip, flaxseed, and guava, which makes 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate a potential biomarker for the consumption of these food products.
CAS Number30737-92-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,4,5,13,21,22,23-Heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoic acidGenerator
2,3-Di-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucopyranosedb_source
Colinindb_source
Collinin?db_source
Cornustannin 3db_source
Tellimagrandin Idb_source
Predicted Properties
PropertyValueSource
Water Solubility1.65 g/LALOGPS
logP2.66ALOGPS
logP2.68ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.34ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area377.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity178.06 m³·mol⁻¹ChemAxon
Polarizability70.91 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC34H26O22
IUPAC name3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(47)55-28-27-18(53-34(51)29(28)56-31(48)9-3-14(37)22(42)15(38)4-9)7-52-32(49)10-5-16(39)23(43)25(45)19(10)20-11(33(50)54-27)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-46,51H,7H2
InChI KeyYKDNTEQLKGYZHT-UHFFFAOYSA-N
Isomeric SMILESOC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=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 Weight786.557
Monoisotopic Molecular Weight786.091572516
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
  • Tetracarboxylic acid or derivatives
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 51.92%; H 3.33%; O 44.75%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 +121.4 (c, 1.3 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTellimagrandin I, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00or-0707239300-3a18f4251ef339f995f8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0417307900-8c46d072e20ac477307cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-0945205800-e150887f40737ad9a699Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0894101000-2810808c4f2dace5e3fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0201014900-eef4b81eaae2d1537cddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1911102300-5d517b1f7fc3cb78ee25Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0902000000-d4a8e80d38ff1e99d5a4Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLMS65-D:LMS68-G
EAFUS IDNot Available
Dr. Duke IDTELLIMAGRANDIN-I|COLININ
BIGG IDNot Available
KNApSAcK IDC00002938
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 hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti lipolyticDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.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.