ContaminantDB: Ureidoisobutyric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:17:14 UTC

Update Date

2026-04-06 12:41:23 UTC

Accession Number

CHEM003261

Identification

Common Name

Ureidoisobutyric acid

Class

Small Molecule

Description

Beta-ureidoisobutyrate (betaUIB) is increased in the urine of patients with beta-ureidopropionase deficiency [EC 3.5.1.6] Ureidoisobutyric acid can be used to predict patient's individual phenotypes of enzyme deficiencies in pyrimidine metabolism when associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil (1, 2).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amide
Amine
Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-((Aminocarbonyl)amino)-2-methylpropanoic acid	ChEBI
3-Ureidoisobutyrate	ChEBI
beta-UBA	ChEBI
beta-Ureidoisobutyric acid	ChEBI
3-((Aminocarbonyl)amino)-2-methylpropanoate	Generator
3-Ureidoisobutyric acid	Generator
b-UBA	Generator
Β-uba	Generator
b-Ureidoisobutyrate	Generator
b-Ureidoisobutyric acid	Generator
beta-Ureidoisobutyrate	Generator
Β-ureidoisobutyrate	Generator
Β-ureidoisobutyric acid	Generator
Ureidoisobutyrate	Generator
3-carbamoylamino-2-Methylpropanoate	HMDB
3-carbamoylamino-2-Methylpropanoic acid	HMDB
DL-beta-Ureidoisobutyrate	HMDB
DL-beta-Ureidoisobutyric acid	HMDB
N-Carbamyl-amino isobutyrate	HMDB
N-Carbamyl-b-aminoisobutyric acid	HMDB
N-Carbamyl-beta-aminoisobutyric acid	HMDB

Chemical Formula

C₅H₁₀N₂O₃

Average Molecular Mass

146.145 g/mol

Monoisotopic Mass

146.069 g/mol

CAS Registry Number

2905-86-4

IUPAC Name

3-(carbamoylamino)-2-methylpropanoic acid

Traditional Name

β-ureidoisobutyric acid

SMILES

CC(CNC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10)

InChI Key

PHENTZNALBMCQD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Ureas

Alternative Parents

Substituents

Urea
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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

ureidocarboxylic acid (CHEBI:1670 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Pyrimidine Metabolism	SMP00046	map00240
Beta Ureidopropionase Deficiency	SMP00172	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	46.1 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-0.88	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.4 m³·mol⁻¹	ChemAxon
Polarizability	13.81 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9100000000-5fb552346f153d8b9141	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9510000000-6396a4042b792437e39a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ug1-4900000000-57fe49b6570a3a56075e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9400000000-d75bc53f6bd893972265	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-505e1e587ff8e3f47c4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-6900000000-d0e112adeac57b5cc676	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfu-9600000000-38cc35413fc058ff2f4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-46efbc5db1bc9c62db04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-8900000000-51286b64a41bad89fd80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05gi-9100000000-835c9b02eecbd89baac8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-40f2b4e3a071943603ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-9dfc177176195ee47192	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9000000000-0f56471f86b7f2230673	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-60a7db0ec3c9213e9347	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0304156

FooDB ID

FDB030465

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

3-UREIDO-ISOBUTYRATE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

141172

ChEBI ID

1670

PubChem Compound ID

Not Available

Kegg Compound ID

C05100

YMDB ID

Not Available

ECMDB ID

ECMDB02031

References

Synthesis Reference

Evans, W. R.; Tsai, Chi Shiun; Axelrod, Bernard. Origin of b-aminoisobutyric acid in iris. Nature (London, United Kingdom) (1961), 190 809.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11675655

Ureidoisobutyric acid (CHEM003261)

Structure for CHEM003261: Ureidoisobutyric acid