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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:38 UTC
Update Date2018-03-12 22:02:41 UTC
HMDB IDHMDB0030412
Secondary Accession Numbers
  • HMDB30412
Metabolite Identification
Common NameTricholomic acid
DescriptionTricholomic acid, also known as tricholomate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Tricholomic acid exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). Within the cell, tricholomic acid is primarily located in the cytoplasm. Outside of the human body, tricholomic acid can be found in mushrooms. This makes tricholomic acid a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
(2S)-amino[(5S)-3-Oxoisoxazolidin-5-yl]acetic acidHMDB
2-(3-oxo-5-Isoxazolidinyl)glycineHMDB
a-amino-3-oxo-5-Isoxazolidineacetic acid, 9ciHMDB
alpha-amino-3-oxo-5-Isoxazolidineacetic acidHMDB
alpha-amino-3-oxo-5-Isoxazolidineacetic acid, (r*,s*)-isomerMeSH
alpha-CycloglutamateMeSH
amino-(3'-Hydroxy-4',5'-dihydroisoxazol-5'-yl)acetic acidMeSH
gamma-CycloglutamateMeSH
Chemical FormulaC5H8N2O4
Average Molecular Weight160.128
Monoisotopic Molecular Weight160.048406754
IUPAC Name2-amino-2-(3-oxo-1,2-oxazolidin-5-yl)acetic acid
Traditional Nameamino(3-oxo-1,2-oxazolidin-5-yl)acetic acid
CAS Registry Number2644-49-7
SMILES
NC(C1CC(=O)NO1)C(O)=O
InChI Identifier
InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)
InChI KeyNTHMUJMQOXQYBR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Oxazolidinone
  • Isoxazolidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility272 g/LALOGPS
logP-3ALOGPS
logP-4ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)1.69ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.3 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-2ae3d33bd3ac15132534View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-5900000000-ca909240062aa058b343View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-3900000000-2fdbdc09190e2cf9c5a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-3d0d338cd1012094f63eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-bce89ee41b291071c29aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3900000000-fbf04f7cc4552e29f616View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-9300000000-965212c5cb22527a1b2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e83ae7ca4d6a8acf12aaView in 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 IDFDB002274
KNApSAcK IDC00001395
Chemspider ID133122
KEGG Compound IDC08298
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151031
PDB IDNot Available
ChEBI ID529821
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.. .