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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 21:13:44 UTC
Update Date2022-09-22 18:35:16 UTC
HMDB IDHMDB0341443
Secondary Accession NumbersNone
Metabolite Identification
Common NameTryptophan N-glucoside
Description2-amino-3-{1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose. 2-amino-3-{1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2-Amino-3-{1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoateGenerator
Chemical FormulaC17H22N2O7
Average Molecular Weight366.37
Monoisotopic Molecular Weight366.142701056
IUPAC Name2-amino-3-{1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid
Traditional Name2-amino-3-{1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl}propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CN(C2OC(CO)C(O)C(O)C2O)C2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=1S/C17H22N2O7/c18-10(17(24)25)5-8-6-19(11-4-2-1-3-9(8)11)16-15(23)14(22)13(21)12(7-20)26-16/h1-4,6,10,12-16,20-23H,5,7,18H2,(H,24,25)
InChI KeyZHBHZDMTVVJASV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub Class1-pyranosylindoles
Direct Parent1-pyranosylindoles
Alternative Parents
Substituents
  • 1-pyranosylindole
  • Hexose monosaccharide
  • Indolyl carboxylic acid derivative
  • Glycosyl compound
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Monosaccharide
  • Oxane
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-1.9ALOGPS
logP-3.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.97ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area158.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.76 m³·mol⁻¹ChemAxon
Polarizability36.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
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 Compound73095692
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub 2021 Mar 19. [PubMed:33739820 ]