MiMeDB: Showing metabocard for Oxamate (MMDBc0030326)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:03:36 UTC

Update Date

2022-08-31 17:43:43 UTC

Metabolite ID

MMDBc0030326

Metabolite Identification

Common Name

Oxamate

Description

Oxamate is an amino-substituted glyoxylic acid derivative. It is believed to be a product of Allantoin degradation in E. coli. Enteric bacteria such as E. coli are able to utilize allantoin as a sole source of nitrogen under anaerobic conditions, but can not utilize it as a sole source of carbon. The first step in allantoin degradation is the opening of the aromatic ring, yielding allantoate, performed by allantoinase. In the next step allantoate is hydrolyzed to S-ureidoglycine by allantoate amidohydrolase. Ureidoglycolate dehydrogenase then oxidizes ureidoglycolate to oxalurate. It is believed oxalurate is converted into oxamate and carbamoyl-phosphate, which can be further metabolized to CO2, ammonia and ATP.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amino(oxo)acetic acid	ChEBI
Oxalic monoamide	ChEBI
Oxamic acid	Kegg
Amino(oxo)acetate	Generator
Acid, oxamidic	MeSH
Aminooxoacetic acid	MeSH
Oxalamic acid	MeSH
Oxamidic acid	MeSH
Acid, oxamic	MeSH
Acid, aminooxoacetic	MeSH
Acid, oxalamic	MeSH

Molecular Formula

C₂H₃NO₃

Average Mass

89.0501

Monoisotopic Mass

89.011292967

IUPAC Name

carbamoylformic acid

Traditional Name

oxamic acid

CAS Registry Number

471-47-6

SMILES

NC(=O)C(O)=O

InChI Identifier

InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)

InChI Key

SOWBFZRMHSNYGE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

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 and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Primary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid monoamide (CHEBI:18058 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	108 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.1	ChemAxon
logS	0.08	ALOGPS
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	16.26 m³·mol⁻¹	ChemAxon
Polarizability	6.65 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-01b9-4900000000-a5c7d6900f929f7102bf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-b801e8d1b363f91332ad	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-45810f38453748a2d26f	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e87e076e2ffe6d08a16b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000f-9000000000-b870b26a5ebffe4dffa5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-371fe3b6dd3cc4f2cd1a	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-68b3969cef554dca4e23	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-785f3a8aab8f2ac5f598	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4f5256271ccf6a7d0e19	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-1348db048c59f511f37f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-7ed633dbb477c19204b2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f3903e56dedef1549964	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010941	Oxalureate	Carbamoylphosphate	Not Available		VMH	30371894
MMDBr0016549	Water	Ammonium	Oxamate amidohydrolase proenzyme	Hydrolysis of bond	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	5	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Bacteroidetes	14	Human feces; Human appendix biopsy; Human stool	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

DB03940

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01444

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxamate

METLIN ID

Not Available

PubChem Compound

974

PDB ID

Not Available

ChEBI ID

18058

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Oxamate (MMDBc0030326)

MOL for #<Metabolite:0x000055e070bec4a8>

3D MOL for #<Metabolite:0x000055e070bec4a8>

3D SDF for #<Metabolite:0x000055e070bec4a8>

3D-SDF for #<Metabolite:0x000055e070bec4a8>

PDB for #<Metabolite:0x000055e070bec4a8>

3D PDB for #<Metabolite:0x000055e070bec4a8>

SMILES for #<Metabolite:0x000055e070bec4a8>

INCHI for #<Metabolite:0x000055e070bec4a8>

Structure for #<Metabolite:0x000055e070bec4a8>

3D Structure for #<Metabolite:0x000055e070bec4a8>