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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:38 UTC

Update Date

2022-03-07 02:52:32 UTC

HMDB ID

HMDB0030412

Secondary Accession Numbers

HMDB30412

Metabolite Identification

Common Name

Tricholomic acid

Description

Tricholomic 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 has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make tricholomic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Tricholomic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tricholomate	Generator
alpha-Amino-3-oxo-5-isoxazolidineacetic acid	MeSH
alpha-Amino-3-oxo-5-isoxazolidineacetic acid, (r,s)-isomer	MeSH
gamma-Cycloglutamate	MeSH
(2S)-amino[(5S)-3-Oxoisoxazolidin-5-yl]acetic acid	HMDB
2-(3-oxo-5-Isoxazolidinyl)glycine	HMDB
a-amino-3-oxo-5-Isoxazolidineacetic acid, 9ci	HMDB
alpha-Cycloglutamate	MeSH, HMDB
amino-(3'-Hydroxy-4',5'-dihydroisoxazol-5'-yl)acetic acid	MeSH, HMDB
2-Amino-2-(3-hydroxy-4,5-dihydro-1,2-oxazol-5-yl)acetate	Generator
Tricholomic acid	MeSH

Chemical Formula

C₅H₈N₂O₄

Average Molecular Weight

160.128

Monoisotopic Molecular Weight

160.048406754

IUPAC Name

2-amino-2-(3-oxo-1,2-oxazolidin-5-yl)acetic acid

Traditional Name

amino(3-oxo-1,2-oxazolidin-5-yl)acetic acid

CAS Registry Number

2644-49-7

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 Key

NTHMUJMQOXQYBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030412)
Cytoplasm (HMDB: HMDB0030412)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030412)

Source

Endogenous

Endogenous (HMDB: HMDB0030412)

Plant

Plant (HMDB: HMDB0030412)

Exogenous

Food

Food (HMDB: HMDB0030412)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0030412)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0030412)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	272 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.3 m³·mol⁻¹	ChemAxon
Polarizability	13.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.87	31661259
DarkChem	[M-H]-	128.985	31661259
DeepCCS	[M+H]+	127.786	30932474
DeepCCS	[M-H]-	124.052	30932474
DeepCCS	[M-2H]-	161.396	30932474
DeepCCS	[M+Na]+	136.528	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.1	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	130.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tricholomic acid	NC(C1CC(=O)NO1)C(O)=O	2572.7	Standard polar	33892256
Tricholomic acid	NC(C1CC(=O)NO1)C(O)=O	1596.6	Standard non polar	33892256
Tricholomic acid	NC(C1CC(=O)NO1)C(O)=O	2254.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tricholomic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1CC(=O)NO1	1700.3	Semi standard non polar	33892256
Tricholomic acid,1TMS,isomer #2	C[Si](C)(C)NC(C(=O)O)C1CC(=O)NO1	1746.9	Semi standard non polar	33892256
Tricholomic acid,1TMS,isomer #3	C[Si](C)(C)N1OC(C(N)C(=O)O)CC1=O	1816.6	Semi standard non polar	33892256
Tricholomic acid,2TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC(=O)NO1	1805.5	Semi standard non polar	33892256
Tricholomic acid,2TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC(=O)NO1	1787.5	Standard non polar	33892256
Tricholomic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)C1CC(=O)N([Si](C)(C)C)O1	1759.0	Semi standard non polar	33892256
Tricholomic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)C1CC(=O)N([Si](C)(C)C)O1	1747.5	Standard non polar	33892256
Tricholomic acid,2TMS,isomer #3	C[Si](C)(C)N(C(C(=O)O)C1CC(=O)NO1)[Si](C)(C)C	1888.4	Semi standard non polar	33892256
Tricholomic acid,2TMS,isomer #3	C[Si](C)(C)N(C(C(=O)O)C1CC(=O)NO1)[Si](C)(C)C	1873.0	Standard non polar	33892256
Tricholomic acid,2TMS,isomer #4	C[Si](C)(C)NC(C(=O)O)C1CC(=O)N([Si](C)(C)C)O1	1876.6	Semi standard non polar	33892256
Tricholomic acid,2TMS,isomer #4	C[Si](C)(C)NC(C(=O)O)C1CC(=O)N([Si](C)(C)C)O1	1783.6	Standard non polar	33892256
Tricholomic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1CC(=O)NO1)N([Si](C)(C)C)[Si](C)(C)C	1910.6	Semi standard non polar	33892256
Tricholomic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1CC(=O)NO1)N([Si](C)(C)C)[Si](C)(C)C	1896.0	Standard non polar	33892256
Tricholomic acid,3TMS,isomer #2	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC(=O)N([Si](C)(C)C)O1	1887.3	Semi standard non polar	33892256
Tricholomic acid,3TMS,isomer #2	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC(=O)N([Si](C)(C)C)O1	1862.7	Standard non polar	33892256
Tricholomic acid,3TMS,isomer #3	C[Si](C)(C)N1OC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC1=O	1937.4	Semi standard non polar	33892256
Tricholomic acid,3TMS,isomer #3	C[Si](C)(C)N1OC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC1=O	1929.5	Standard non polar	33892256
Tricholomic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1CC(=O)N([Si](C)(C)C)O1)N([Si](C)(C)C)[Si](C)(C)C	1992.9	Semi standard non polar	33892256
Tricholomic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1CC(=O)N([Si](C)(C)C)O1)N([Si](C)(C)C)[Si](C)(C)C	1980.7	Standard non polar	33892256
Tricholomic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1CC(=O)NO1	1945.6	Semi standard non polar	33892256
Tricholomic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1CC(=O)NO1	1991.5	Semi standard non polar	33892256
Tricholomic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1OC(C(N)C(=O)O)CC1=O	1997.4	Semi standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)NO1	2252.8	Semi standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)NO1	2221.5	Standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2201.0	Semi standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2221.1	Standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1CC(=O)NO1)[Si](C)(C)C(C)(C)C	2298.3	Semi standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1CC(=O)NO1)[Si](C)(C)C(C)(C)C	2292.6	Standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2271.6	Semi standard non polar	33892256
Tricholomic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2224.2	Standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1CC(=O)NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2532.1	Semi standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1CC(=O)NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2535.2	Standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2496.3	Semi standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)N([Si](C)(C)C(C)(C)C)O1	2496.5	Standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1OC(C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=O	2537.5	Semi standard non polar	33892256
Tricholomic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1OC(C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=O	2555.6	Standard non polar	33892256
Tricholomic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1CC(=O)N([Si](C)(C)C(C)(C)C)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2761.2	Semi standard non polar	33892256
Tricholomic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1CC(=O)N([Si](C)(C)C(C)(C)C)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2777.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tricholomic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-2ae3d33bd3ac15132534	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tricholomic acid GC-MS (1 TMS) - 70eV, Positive	splash10-014i-5900000000-ca909240062aa058b343	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tricholomic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 10V, Positive-QTOF	splash10-01ox-3900000000-2fdbdc09190e2cf9c5a5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 20V, Positive-QTOF	splash10-014i-5900000000-3d0d338cd1012094f63e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 40V, Positive-QTOF	splash10-056r-9000000000-bce89ee41b291071c29a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 10V, Negative-QTOF	splash10-0a4i-3900000000-fbf04f7cc4552e29f616	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 20V, Negative-QTOF	splash10-001r-9300000000-965212c5cb22527a1b2e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 40V, Negative-QTOF	splash10-0006-9000000000-e83ae7ca4d6a8acf12aa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 10V, Negative-QTOF	splash10-0pb9-2900000000-44c6b3bf8d78352efcec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 20V, Negative-QTOF	splash10-052f-9100000000-a1365ee6fa433766a246	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 40V, Negative-QTOF	splash10-0016-9000000000-2f765aae3dc736509ad5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 10V, Positive-QTOF	splash10-014i-2900000000-24fa730ca065fbdf614b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 20V, Positive-QTOF	splash10-014j-9800000000-6e5f27be11e012f95838	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricholomic acid 40V, Positive-QTOF	splash10-0aba-9000000000-678251846addb4cd4cb6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tricholomic acid

METLIN ID

Not Available

PubChem Compound

151031

PDB ID

Not Available

ChEBI ID

529821

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Tricholomic acid (HMDB0030412)

MOL for HMDB0030412 (Tricholomic acid)

3D MOL for HMDB0030412 (Tricholomic acid)

3D SDF for HMDB0030412 (Tricholomic acid)

3D-SDF for HMDB0030412 (Tricholomic acid)

PDB for HMDB0030412 (Tricholomic acid)

3D PDB for HMDB0030412 (Tricholomic acid)

SMILES for HMDB0030412 (Tricholomic acid)

INCHI for HMDB0030412 (Tricholomic acid)

Structure for HMDB0030412 (Tricholomic acid)

3D Structure for HMDB0030412 (Tricholomic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra