Record Information
Version1.0
Creation date2010-04-08 22:13:56 UTC
Update date2019-11-26 03:16:42 UTC
Primary IDFDB018801
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSanguiin H2
DescriptionSanguiin H2 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. Sanguiin H2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Sanguiin H2 has been detected, but not quantified in, a few different foods, such as herbs and spices, red raspberries, and tea. This could make sanguiin H2 a potential biomarker for the consumption of these foods.
CAS Number82200-04-2
Structure
Thumb
Synonyms
SynonymSource
1-O-Galloyl-2,3-(S)-hexahydroxydiphenoyl-4,6-sanguisorboyl-a-D-glucopyranosedb_source
Sanguiin H-2biospider
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP3.63ALOGPS
logP4.09ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area531.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity250.36 m³·mol⁻¹ChemAxon
Polarizability96.91 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H32O31
IUPAC name3-{[(1R,2S,19R,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-20-(3,4,5-trihydroxybenzoyloxy)-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5,7,9,11,13,15,26,28,30,32(37),33,35-dodecaen-36-yl]oxy}-4,5-dihydroxybenzoic acid
InChI IdentifierInChI=1S/C48H32O31/c49-14-2-10(3-15(50)27(14)55)43(68)79-48-41-40(77-45(70)12-6-18(53)29(57)32(60)22(12)23-13(46(71)78-41)7-19(54)30(58)33(23)61)38-21(75-48)8-73-44(69)11-5-17(52)31(59)34(62)24(11)25-26(47(72)76-38)39(37(65)36(64)35(25)63)74-20-4-9(42(66)67)1-16(51)28(20)56/h1-7,21,38,40-41,48-65H,8H2,(H,66,67)/t21-,38-,40+,41-,48-/m1/s1
InChI KeyVQIUUNUVZNWSSC-PVQGVBEGSA-N
Isomeric SMILESOC(=O)C1=CC(O)=C(O)C(OC2=C3C(=C(O)C(O)=C2O)C2=C(C=C(O)C(O)=C2O)C(=O)OC[C@H]2O[C@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H]4OC(=O)C5=CC(O)=C(O)C(O)=C5C5=C(C=C(O)C(O)=C5O)C(=O)O[C@H]4[C@@H]2OC3=O)=C1
Average Molecular Weight1104.7491
Monoisotopic Molecular Weight1104.092754306
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
  • Hexacarboxylic acid or derivatives
  • Galloyl ester
  • Gallic acid or derivatives
  • Dihydroxybenzoic acid
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Diaryl ether
  • Hydroxybenzoic acid
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Pyrogallol derivative
  • Phenoxy compound
  • Catechol
  • Benzoyl
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 52.19%; H 2.92%; O 44.89%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 +7.9 (c, 0.98 in Me2CO)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 ID74079453
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39262
CRC / DFC (Dictionary of Food Compounds) IDLMS32-R:LMS32-R
EAFUS IDNot Available
Dr. Duke IDSANGUIIN-H-2
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
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
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).