Record Information
Version1.0
Creation date2010-04-08 22:13:57 UTC
Update date2019-11-26 03:16:43 UTC
Primary IDFDB018813
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGranatin A
DescriptionGranatin A 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. Granatin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Granatin A has been detected, but not quantified in, fruits and pomegranates. This could make granatin a a potential biomarker for the consumption of these foods.
CAS Number73683-70-2
Structure
Thumb
Synonyms
SynonymSource
1,6-(S)-Hexahydroxydiphenoyl-2,4-(S)-dehydrohexahydroxydiphenoyl-b-D-glucopyranosedb_source
Predicted Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP1.48ALOGPS
logP0.13ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.65ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area374.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity173.59 m³·mol⁻¹ChemAxon
Polarizability68.81 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC34H24O22
IUPAC name(1R,2R,19R,20S,29S,31S,37S)-6,7,8,11,12,13,25,26,30,30,31,37-dodecahydroxy-17,21,36,38,39-pentaoxaoctacyclo[18.16.1.1^{2,19}.1^{27,31}.0^{4,9}.0^{10,15}.0^{23,28}.0^{29,34}]nonatriaconta-4,6,8,10,12,14,23,25,27,33-decaene-3,16,22,32,35-pentone
InChI IdentifierInChI=1S/C34H24O22/c35-10-1-6-15(23(43)20(10)40)16-7(2-11(36)21(41)24(16)44)30(46)52-5-13-26-25(45)29(28(53-13)19(6)39)55-32(48)9-4-14(38)34(51)33(49,50)18(9)17-8(31(47)54-26)3-12(37)22(42)27(17)56-34/h1-4,13,18,25-26,28-29,35-37,40-45,49-51H,5H2/t13-,18-,25+,26-,28+,29-,34-/m1/s1
InChI KeyBEAQEKRAXFQCBO-AHMBPAJWSA-N
Isomeric SMILES[H][C@@]12C3=CC(=O)[C@@](O)(OC4=C1C(=CC(O)=C4O)C(=O)O[C@@H]1[C@H]4COC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(O)C(O)=C(O)C=C5C(=O)[C@H](O4)[C@H](OC3=O)[C@H]1O)C2(O)O
Average Molecular Weight784.5412
Monoisotopic Molecular Weight784.075922452
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
  • Gallic acid or derivatives
  • Dihydroxybenzoic acid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Tricarboxylic acid or derivatives
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Ketone
  • Polyol
  • Carbonyl hydrate
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.05%; H 3.08%; O 44.86%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 +9.5 (c, 0.5 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot 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 IDHMDB39271
CRC / DFC (Dictionary of Food Compounds) IDLMT18-W:LMT18-W
EAFUS IDNot Available
Dr. Duke IDGRANATIN-A
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti peroxidantDUKE
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).