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Showing Compound 2-O-Galloyl-(4S,6S)-gallagoyl-D-glucose (FDB006760)

Record Information
Version1.0
Creation date2010-04-08 22:07:17 UTC
Update date2019-11-26 03:01:17 UTC
Primary IDFDB006760
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-O-Galloyl-(4S,6S)-gallagoyl-D-glucose
Description2-O-Galloyl-(4S,6S)-gallagoyl-D-glucose 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. 2-O-Galloyl-(4S,6S)-gallagoyl-D-glucose has been detected, but not quantified in, pomegranates (Punica granatum). This could make 2-O-galloyl-(4S,6S)-gallagoyl-D-glucose a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-O-Galloyl-(4S,6S)-gallagoyl-D-glucose.
CAS Number95-01-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.65 g/LALOGPS
logP2.76ALOGPS
logP2.72ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area427.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity211.25 m³·mol⁻¹ChemAxon
Polarizability83.89 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC41H28O25
IUPAC name(10S,11S,12R,13R,15R)-3,4,5,11,13,21,22,23,26,27,38,39-dodecahydroxy-8,18,35-trioxo-9,14,17,29,36-pentaoxaoctacyclo[29.8.0.0²,⁷.0¹⁰,¹⁵.0¹⁹,²⁴.0²⁵,³⁴.0²⁸,³³.0³²,³⁷]nonatriaconta-1(31),2,4,6,19,21,23,25,27,32(37),33,38-dodecaen-12-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C41H28O25/c42-11-1-7(2-12(43)23(11)46)37(56)66-36-32(55)33-15(63-41(36)60)6-62-38(57)8-3-13(44)25(48)27(50)17(8)20-22-21-19-10(5-61-34(21)30(53)29(20)52)18(28(51)31(54)35(19)65-40(22)59)16-9(39(58)64-33)4-14(45)24(47)26(16)49/h1-4,15,32-33,36,41-55,60H,5-6H2/t15-,32+,33-,36-,41-/m1/s1
InChI KeyJMCHOJWVWCHHFC-MUAAPLJWSA-N
Isomeric SMILESO[C@@H]1O[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C4OCC5=C(C(O)=C(O)C6=C5C4=C3C(=O)O6)C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]2[C@H](O)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight920.646
Monoisotopic Molecular Weight920.091966446
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
  • Macrolide
  • 7,8-dihydroxycoumarin
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Isocoumarin
  • Coumarin
  • Benzoate ester
  • Benzopyran
  • 1-benzopyran
  • 2-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0611061519-888392d4c04759cb47da2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900071655-02c7a942c98d68e42f322016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-0800390000-daf3d507c05f03c767a52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0810005597-ce63210c9477387e7a922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1910000111-04a1480e3823983422722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-1900001000-717053c94736b70a3bc52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0200000009-e81c4274ee763fb99cd22021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0910003323-c5a5d3873972815b6da02021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-3800006980-92d477a9eacd6590caae2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000009-3fd6d93fc80c8b8c23822021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0500000349-743f6a7f7d75e6cdeb7c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1920004441-8ec02c64282521cc90ef2021-10-21View Spectrum
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) IDNot Available
EAFUS IDNot Available
Dr. Duke ID2-O-GALLOYL-4,6(S,S)-GALLAGOYL-D-GLUCOSE
BIGG IDNot Available
KNApSAcK IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. TAKASHI T, GEN-ICHIRO N, ITSUO N. Tannins and Related Compounds. XL.: Revision of the Structures of Punicalin and Punicalagin, and Isolation and Characterization of 2-O-Galloylpunicalin from the Bark of Punica granatum L. Chemical & pharmaceutical bulletin. 1986 Feb 25;34(2):650–5. [No PubMed ID] Article [Isolation]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).