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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2019-07-16 17:53:44 UTC
Update Date2019-10-24 17:45:44 UTC
HMDB IDHMDB0240379
Secondary Accession NumbersNone
Metabolite Identification
Common NameHHPAA glucuronide
DescriptionHHPAA glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563892759
Synonyms
ValueSource
2-Hydroxy-N-(2-hydroxyphenyl)acetamide glucuronideHMDB
HHPAA glucuronideHMDB
Chemical FormulaC14H17NO9
Average Molecular Weight343.288
Monoisotopic Molecular Weight343.090331131
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(2-hydroxyacetamido)phenoxy]oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(2-hydroxyacetamido)phenoxy]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OCC(=O)NC1=CC=CC=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C14H17NO9/c16-5-8(17)15-6-3-1-2-4-7(6)23-14-11(20)9(18)10(19)12(24-14)13(21)22/h1-4,9-12,14,16,18-20H,5H2,(H,15,17)(H,21,22)/t9-,10-,11+,12-,14+/m0/s1
InChI KeyFGIQLOOXJCVVDO-BYNIDDHOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
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
logP-0.98ALOGPS
logP-1.9ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.62 m³·mol⁻¹ChemAxon
Polarizability31.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
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 CompoundNot Available
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. Beckmann M, Lloyd AJ, Haldar S, Seal C, Brandt K, Draper J: Hydroxylated phenylacetamides derived from bioactive benzoxazinoids are bioavailable in humans after habitual consumption of whole grain sourdough rye bread. Mol Nutr Food Res. 2013 Oct;57(10):1859-73. doi: 10.1002/mnfr.201200777. Epub 2013 May 16. [PubMed:23681766 ]
  2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]