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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:49 UTC
Update Date2019-07-23 06:14:19 UTC
HMDB IDHMDB0033785
Secondary Accession Numbers
  • HMDB33785
Metabolite Identification
Common NameHamamelitannin
DescriptionHamamelitannin is found in nuts. Hamamelitannin is isolated from Castanea sativa (sweet chestnut).
Structure
Data?1563862459
Synonyms
ValueSource
2',5-DigalloylhamamelofuranoseHMDB
2,3-Di-O-galloyl-D-glucoseHMDB
2,3-DigalloylglucoseHMDB
Chemical FormulaC20H20O14
Average Molecular Weight484.3644
Monoisotopic Molecular Weight484.085305348
IUPAC Name{3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl}methyl 3,4,5-trihydroxybenzoate
Traditional Name{3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl}methyl 3,4,5-trihydroxybenzoate
CAS Registry Number469-32-9
SMILES
OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1(O)COC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C20H20O14/c21-9-1-7(2-10(22)14(9)25)17(28)32-5-13-16(27)20(31,19(30)34-13)6-33-18(29)8-3-11(23)15(26)12(24)4-8/h1-4,13,16,19,21-27,30-31H,5-6H2
InChI KeyFEPAFOYQTIEEIS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGalloyl esters
Alternative Parents
Substituents
  • Galloyl ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Pentose monosaccharide
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP0.89ALOGPS
logP0.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area243.9 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.67 m³·mol⁻¹ChemAxon
Polarizability45.03 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2973300000-8e8de53696948f8dbff0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0w4r-8984214000-b66a034c7cdf78f5b165JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0756900000-ffc79e6526813be28daaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gba-0924200000-e83ec2aaa98c793d9d4dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0910000000-3b2eb3f9894aea9e739cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-1912500000-313cc8ab47836e5178c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0901000000-7a9d822929bffc84bf86JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0900000000-352dc7cb29d29dde220cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011943
KNApSAcK IDNot Available
Chemspider ID222425
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound253775
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .