QUEBRACHO BARK EXTRACT (CHEM007383)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:24:55 UTC
Update Date2016-11-09 01:09:55 UTC
Accession NumberCHEM007383
Identification
Common NameQUEBRACHO BARK EXTRACT
ClassSmall Molecule
DescriptionAn ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(beta-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)ChEBI
1-O-Galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranoseChEBI
(b-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)Generator
(Β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-b-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenate-beta-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenate-β-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-b-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-β-D-glucopyranoseGenerator
1-O-Galloyl-3,6-(R)-hexahydroxydiphenol-beta-D-glucoseMeSH
CorillaginHMDB
Chemical FormulaC27H22O18
Average Molecular Mass634.453 g/mol
Monoisotopic Mass634.081 g/mol
CAS Registry Number977092-71-9
IUPAC Name(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate
Traditional Name(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate
SMILESO[C@@H]1[C@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2
InChI IdentifierInChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1
InChI KeyTUSDEZXZIZRFGC-XIGLUPEJSA-N
Chemical Taxonomy
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
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Pyrogallol derivative
  • Tricarboxylic acid or derivatives
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.9 g/LALOGPS
logP1.69ALOGPS
logP1.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.41ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area310.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity142.3 m³·mol⁻¹ChemAxon
Polarizability55.34 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kk9-1400901000-f9ee94000466cc2a5d98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0912102000-747eb30db0e36223c7d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910100000-c09c146b163418500f06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-0930000000-7dda7b5a680cd0912f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-0900214000-ac8138ca0eb7e3474411Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900301000-bedf60486b80a8240cc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lfu-4920200000-73686c08722f918b4f00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0400709000-974c3fccc24061e5bfcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-1900801000-39727df01a08af3c68c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3900420000-d3d45ea63d8935f0bd13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0900101000-19cd1c40012f2b1310f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i29-0900522000-f1a8081561856ad5378dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-5900750000-0bf5a21943a40e85788bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031457
FooDB IDFDB006774
Phenol Explorer IDNot Available
KNApSAcK IDC00002915
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCorilagin
Chemspider ID66248
ChEBI ID3884
PubChem Compound ID73568
Kegg Compound IDC10219
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18486919
2. Shen ZQ, Dong ZJ, Peng H, Liu JK: Modulation of PAI-1 and tPA activity and thrombolytic effects of corilagin. Planta Med. 2003 Dec;69(12):1109-12.
3. Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.