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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 01:30:05 UTC
Update Date2019-11-12 17:21:33 UTC
HMDB IDHMDB0128334
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid
Description2-[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid 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. This glycination-of-aryl-acid occurs in humans. 2-[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by Glycine N-acyltransferase (Q6IB77) enzyme via a glycination-of-aryl-acid reaction. 2--2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3--2,4,5-trihydroxybenzoic acid.
Structure
Data?1563875373
Synonyms
ValueSource
2-[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetateGenerator
Chemical FormulaC23H17NO15
Average Molecular Weight547.381
Monoisotopic Molecular Weight547.059818851
IUPAC Name2-[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid
Traditional Name[({3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-2,4,5-trihydroxyphenyl}(hydroxy)methylidene)amino]acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CN=C(O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)=C1O
InChI Identifier
InChI=1S/C23H17NO15/c25-10-1-7(2-11(26)17(10)32)22(36)38-14-4-8(3-12(27)18(14)33)23(37)39-20-16(31)9(5-13(28)19(20)34)21(35)24-6-15(29)30/h1-5,25-28,31-34H,6H2,(H,24,35)(H,29,30)
InChI KeyCAHKHOKBBCCQIM-UHFFFAOYSA-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
  • Depside backbone
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Galloyl ester
  • Hexose monosaccharide
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • O-glycosyl compound
  • Glycosyl compound
  • M-hydroxybenzoic acid ester
  • Hydroxybenzoic acid
  • Benzoate ester
  • Phenol ester
  • Salicylic acid or derivatives
  • Salicylic acid
  • Pyrogallol derivative
  • Benzoic acid
  • Benzoic acid or derivatives
  • 4-alkoxyphenol
  • Benzenetriol
  • Benzoyl
  • Phenol ether
  • Phenoxy compound
  • Resorcinol
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.26ALOGPS
logP4.84ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area284.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.09 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0pb9-1907002000-e08ff663b37784b8cf33Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-0917110000-bbd6002de5481ba68602Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zis-2424090000-f9db10507cc916614a64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zor-6925160000-cddddf3e0095da898a14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2901000000-46ac4b52617586e1f21dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0312090000-f14a9ae14942c4e951f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02k9-1933130000-443f8248042e5fa54c90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01di-0911000000-6168ff702cebaa37037bSpectrum
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131834674
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. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.