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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-03-04 20:25:33 UTC
Update Date2021-09-14 15:37:34 UTC
HMDB IDHMDB0059794
Secondary Accession Numbers
  • HMDB59794
Metabolite Identification
Common NameGluten exorphin B4
DescriptionGluten exorphin B4 is a tetrapeptide with the sequence Tyr-Gly-Gly-Trp. Gluten exorphins are a group of opioid peptides which are formed during digestion of the gluten protein. It has been hypothesized that people with autism and schizophrenia have abnormal leakage from the gut of these compounds, which then pass into the brain and disrupt brain function. This is partly the basis for the gluten-free, casein-free diet. The scientific evidence for this diet and its effects is still disputed.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H27N5O9
Average Molecular Weight529.4993
Monoisotopic Molecular Weight529.180877487
IUPAC Name(2S)-2-({[2-({[2-({[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]oxy}amino)acetyl]oxy}amino)acetyl]oxy}amino)-3-(1H-indol-3-yl)propanoic acid
Traditional Name(2S)-2-({[2-({[2-({[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]oxy}amino)acetyl]oxy}amino)acetyl]oxy}amino)-3-(1H-indol-3-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CC1=CC=C(O)C=C1)C(=O)ONCC(=O)ONCC(=O)ON[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=1S/C24H27N5O9/c25-18(9-14-5-7-16(30)8-6-14)24(35)38-28-12-21(31)36-27-13-22(32)37-29-20(23(33)34)10-15-11-26-19-4-2-1-3-17(15)19/h1-8,11,18,20,26-30H,9-10,12-13,25H2,(H,33,34)/t18-,20-/m0/s1
InChI KeyWHGKXKRERBUEES-ICSRJNTNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Tetracarboxylic acid or derivatives
  • Indolyl carboxylic acid derivative
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid salt
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Organic salt
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
Predicted Chromatographic Properties
Spectra
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 Compound131769782
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 ReferencesNot Available