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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:39:13 UTC

Update Date

2021-09-23 22:39:13 UTC

HMDB ID

HMDB0303019

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxaluric acid

Description

Oxalureate, also known as monooxalylurea or oxaluric acid, is a member of the class of compounds known as N-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom. Oxalureate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxalureate can be found in cocoa bean, which makes oxalureate a potential biomarker for the consumption of this food product. Oxalureate may be a unique E.coli metabolite.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monooxalylurea	ChEBI
Onooxalylurea	ChEBI
Oxal	ChEBI
Oxalurate	ChEBI
Ureido(oxo)acetic acid	ChEBI
Oxaluric acid	Kegg
N-Carbamoyl-2-oxoglycine	Kegg
Ureido(oxo)acetate	Generator
Oxalate	Generator
Oxalic acid	Generator
Oxalureic acid	Generator
Oxalureate	ChEBI
Carbamoyloxamic acid	MeSH

Chemical Formula

C₃H₄N₂O₄

Average Molecular Weight

132.0749

Monoisotopic Molecular Weight

132.017106626

IUPAC Name

2-hydroxy-2-[(C-hydroxycarbonimidoyl)imino]acetic acid

Traditional Name

oxalureate

CAS Registry Number

Not Available

SMILES

OC(=N)N=C(O)C(O)=O

InChI Identifier

InChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9)

InChI Key

UWBHMRBRLOJJAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-carbamoyl-alpha amino acids

Alternative Parents

Substituents

N-carbamoyl-alpha-amino acid
N-acyl urea
Ureide
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ureas (CHEBI:16582 )
2-oxo monocarboxylic acid (CHEBI:16582 )

Ontology

Not Available

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

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	-0.95	ALOGPS
logP	-0.83	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.67	ChemAxon
pKa (Strongest Basic)	2.25	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.96 m³·mol⁻¹	ChemAxon
Polarizability	10.18 Å³	ChemAxon
Number of Rings	0	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
AllCCS	[M+H]+	131.587	32859911
AllCCS	[M+H-H2O]+	127.494	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M+NH4]+	135.401	32859911
AllCCS	[M-H]-	121.933	32859911
AllCCS	[M+Na-2H]-	124.625	32859911
AllCCS	[M+HCOO]-	127.61	32859911
DeepCCS	[M+H]+	122.414	30932474
DeepCCS	[M-H]-	119.178	30932474
DeepCCS	[M-2H]-	156.043	30932474
DeepCCS	[M+Na]+	131.018	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxaluric acid,4TMS,isomer #1	C[Si](C)(C)N=C(N=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1587.0	Semi standard non polar	33892256
Oxaluric acid,4TMS,isomer #1	C[Si](C)(C)N=C(N=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1560.5	Standard non polar	33892256
Oxaluric acid,4TMS,isomer #1	C[Si](C)(C)N=C(N=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2075.9	Standard polar	33892256
Oxaluric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2344.3	Semi standard non polar	33892256
Oxaluric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2208.0	Standard non polar	33892256
Oxaluric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2420.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxaluric acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2022-08-08	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 - Oxaluric acid 10V, Positive-QTOF	splash10-001l-6900000000-89b582944cfa9e667b3e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 20V, Positive-QTOF	splash10-0006-9200000000-79e0dd9893858427f593	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 40V, Positive-QTOF	splash10-0006-9000000000-f8ad208f216969821a11	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 10V, Negative-QTOF	splash10-0016-9200000000-0d17e2737fb242f68e5d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 20V, Negative-QTOF	splash10-000i-9100000000-2977dfd713e2fe23805f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 40V, Negative-QTOF	splash10-0006-9000000000-359df73a651849f4c789	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 10V, Positive-QTOF	splash10-000x-9600000000-2b45bd093a0b05976381	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 20V, Positive-QTOF	splash10-0006-9000000000-3ad51a133db8e28f97c6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 40V, Positive-QTOF	splash10-0006-9000000000-ed34202536dafd502fa1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 10V, Negative-QTOF	splash10-000f-9000000000-f42c28ea78c3f31ed79d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 20V, Negative-QTOF	splash10-0006-9000000000-fe12a3892eeab52d5665	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxaluric acid 40V, Negative-QTOF	splash10-0006-9000000000-70ff4ec4b719b2aa2329	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16582

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

Not Available

Showing metabocard for Oxaluric acid (HMDB0303019)

MOL for HMDB0303019 (Oxaluric acid)

3D MOL for HMDB0303019 (Oxaluric acid)

3D SDF for HMDB0303019 (Oxaluric acid)

3D-SDF for HMDB0303019 (Oxaluric acid)

PDB for HMDB0303019 (Oxaluric acid)

3D PDB for HMDB0303019 (Oxaluric acid)

SMILES for HMDB0303019 (Oxaluric acid)

INCHI for HMDB0303019 (Oxaluric acid)

Structure for HMDB0303019 (Oxaluric acid)

3D Structure for HMDB0303019 (Oxaluric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra