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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:44:28 UTC

Update Date

2021-09-26 23:06:28 UTC

HMDB ID

HMDB0253330

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ibotenic acid

Description

2-amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetic acid 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). Based on a literature review very few articles have been published on 2-amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ibotenic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ibotenic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetate	Generator
(+/-)-ibotenic acid	ChEMBL
(+/-)-ibotenate	Generator
Ibotenate	Generator
Acid, ibotenic	MeSH

Chemical Formula

C₅H₆N₂O₄

Average Molecular Weight

158.113

Monoisotopic Molecular Weight

158.032756681

IUPAC Name

2-amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetic acid

Traditional Name

ibotenic acid

CAS Registry Number

Not Available

SMILES

NC(C(O)=O)C1=CC(O)=NO1

InChI Identifier

InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)

InChI Key

IRJCBFDCFXCWGO-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
Aralkylamine
Azole
Isoxazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:5854 )
Mushroom toxins (C10600 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0253330)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	-2.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	1	ChemAxon
pKa (Strongest Basic)	6.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.98 m³·mol⁻¹	ChemAxon
Polarizability	13.4 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
DeepCCS	[M+H]+	131.622	30932474
DeepCCS	[M-H]-	129.015	30932474
DeepCCS	[M-2H]-	165.417	30932474
DeepCCS	[M+Na]+	140.506	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	138.3	32859911
AllCCS	[M+Na]+	139.5	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	130.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ibotenic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	1717.5	Semi standard non polar	33892256
Ibotenic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	1590.0	Standard non polar	33892256
Ibotenic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	2755.1	Standard polar	33892256
Ibotenic acid,1TMS,isomer #2	C[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	1685.7	Semi standard non polar	33892256
Ibotenic acid,1TMS,isomer #2	C[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	1522.0	Standard non polar	33892256
Ibotenic acid,1TMS,isomer #2	C[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	3074.9	Standard polar	33892256
Ibotenic acid,1TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	1839.3	Semi standard non polar	33892256
Ibotenic acid,1TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	1582.7	Standard non polar	33892256
Ibotenic acid,1TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	2890.6	Standard polar	33892256
Ibotenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C)=NO1	1639.2	Semi standard non polar	33892256
Ibotenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C)=NO1	1663.3	Standard non polar	33892256
Ibotenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C)=NO1	2401.2	Standard polar	33892256
Ibotenic acid,2TMS,isomer #2	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O)=NO1	1806.9	Semi standard non polar	33892256
Ibotenic acid,2TMS,isomer #2	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O)=NO1	1678.6	Standard non polar	33892256
Ibotenic acid,2TMS,isomer #2	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O)=NO1	2275.6	Standard polar	33892256
Ibotenic acid,2TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C)=NO1	1719.9	Semi standard non polar	33892256
Ibotenic acid,2TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C)=NO1	1634.2	Standard non polar	33892256
Ibotenic acid,2TMS,isomer #3	C[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C)=NO1	2375.0	Standard polar	33892256
Ibotenic acid,2TMS,isomer #4	C[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C	1960.1	Semi standard non polar	33892256
Ibotenic acid,2TMS,isomer #4	C[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C	1767.7	Standard non polar	33892256
Ibotenic acid,2TMS,isomer #4	C[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C	2481.1	Standard polar	33892256
Ibotenic acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O[Si](C)(C)C)=NO1	1724.4	Semi standard non polar	33892256
Ibotenic acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O[Si](C)(C)C)=NO1	1710.4	Standard non polar	33892256
Ibotenic acid,3TMS,isomer #1	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC(O[Si](C)(C)C)=NO1	2044.8	Standard polar	33892256
Ibotenic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C)[Si](C)(C)C	1900.0	Semi standard non polar	33892256
Ibotenic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C)[Si](C)(C)C	1848.1	Standard non polar	33892256
Ibotenic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C)[Si](C)(C)C	2141.5	Standard polar	33892256
Ibotenic acid,3TMS,isomer #3	C[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1871.3	Semi standard non polar	33892256
Ibotenic acid,3TMS,isomer #3	C[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1777.9	Standard non polar	33892256
Ibotenic acid,3TMS,isomer #3	C[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2165.0	Standard polar	33892256
Ibotenic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C)=NO1)N([Si](C)(C)C)[Si](C)(C)C	1880.8	Semi standard non polar	33892256
Ibotenic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C)=NO1)N([Si](C)(C)C)[Si](C)(C)C	1844.6	Standard non polar	33892256
Ibotenic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C)=NO1)N([Si](C)(C)C)[Si](C)(C)C	1971.7	Standard polar	33892256
Ibotenic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	1967.3	Semi standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	1801.3	Standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O)=NO1	2770.3	Standard polar	33892256
Ibotenic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	1914.3	Semi standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	1740.2	Standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NOC(C(N)C(=O)O)=C1	3100.7	Standard polar	33892256
Ibotenic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	2069.7	Semi standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	1793.2	Standard non polar	33892256
Ibotenic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O)=NO1	2843.1	Standard polar	33892256
Ibotenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2110.7	Semi standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2071.8	Standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2502.5	Standard polar	33892256
Ibotenic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O)=NO1	2262.7	Semi standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O)=NO1	2082.4	Standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O)=NO1	2414.5	Standard polar	33892256
Ibotenic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2205.3	Semi standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2044.1	Standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2487.3	Standard polar	33892256
Ibotenic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2392.8	Semi standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2143.3	Standard non polar	33892256
Ibotenic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2515.5	Standard polar	33892256
Ibotenic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2371.2	Semi standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2314.4	Standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC(O[Si](C)(C)C(C)(C)C)=NO1	2402.1	Standard polar	33892256
Ibotenic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2531.6	Semi standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2431.9	Standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2445.6	Standard polar	33892256
Ibotenic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2520.2	Semi standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2378.1	Standard non polar	33892256
Ibotenic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NOC(C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2445.0	Standard polar	33892256
Ibotenic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C(C)(C)C)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2681.9	Semi standard non polar	33892256
Ibotenic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C(C)(C)C)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2612.5	Standard non polar	33892256
Ibotenic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC(O[Si](C)(C)C(C)(C)C)=NO1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2430.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ibotenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9500000000-154d9c934b1fcfc59ea5	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibotenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibotenic 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 - Ibotenic acid 10V, Negative-QTOF	splash10-0a4i-2900000000-2fa11a28130d63bfa6a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibotenic acid 20V, Negative-QTOF	splash10-052f-9200000000-e40e2a21b5e03b8556e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibotenic acid 40V, Negative-QTOF	splash10-0k96-9000000000-a06a3fd0a2585ee8c394	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibotenic acid 10V, Positive-QTOF	splash10-0229-6900000000-6f67d14f55da68213134	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibotenic acid 20V, Positive-QTOF	splash10-03di-7900000000-55f60f015d2a30ac73a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibotenic acid 40V, Positive-QTOF	splash10-1003-9000000000-ac04fb7375d85137253d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00002345

Chemspider ID

1196

KEGG Compound ID

C10600

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1233

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1700111

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Ibotenic acid (HMDB0253330)

MOL for HMDB0253330 (Ibotenic acid)

3D MOL for HMDB0253330 (Ibotenic acid)

3D SDF for HMDB0253330 (Ibotenic acid)

3D-SDF for HMDB0253330 (Ibotenic acid)

PDB for HMDB0253330 (Ibotenic acid)

3D PDB for HMDB0253330 (Ibotenic acid)

SMILES for HMDB0253330 (Ibotenic acid)

INCHI for HMDB0253330 (Ibotenic acid)

Structure for HMDB0253330 (Ibotenic acid)

3D Structure for HMDB0253330 (Ibotenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra