Ureidoisobutyric acid (CHEM003261)

Record Information
Version1.0
Creation Date2014-08-29 06:17:14 UTC
Update Date2026-04-06 12:41:23 UTC
Accession NumberCHEM003261
Identification
Common NameUreidoisobutyric acid
ClassSmall 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-((Aminocarbonyl)amino)-2-methylpropanoic acidChEBI
3-UreidoisobutyrateChEBI
beta-UBAChEBI
beta-Ureidoisobutyric acidChEBI
3-((Aminocarbonyl)amino)-2-methylpropanoateGenerator
3-Ureidoisobutyric acidGenerator
b-UBAGenerator
Β-ubaGenerator
b-UreidoisobutyrateGenerator
b-Ureidoisobutyric acidGenerator
beta-UreidoisobutyrateGenerator
Β-ureidoisobutyrateGenerator
Β-ureidoisobutyric acidGenerator
UreidoisobutyrateGenerator
3-carbamoylamino-2-MethylpropanoateHMDB
3-carbamoylamino-2-Methylpropanoic acidHMDB
DL-beta-UreidoisobutyrateHMDB
DL-beta-Ureidoisobutyric acidHMDB
N-Carbamyl-amino isobutyrateHMDB
N-Carbamyl-b-aminoisobutyric acidHMDB
N-Carbamyl-beta-aminoisobutyric acidHMDB
Chemical FormulaC5H10N2O3
Average Molecular Mass146.145 g/mol
Monoisotopic Mass146.069 g/mol
CAS Registry Number2905-86-4
IUPAC Name3-(carbamoylamino)-2-methylpropanoic acid
Traditional Nameβ-ureidoisobutyric acid
SMILESCC(CNC(N)=O)C(O)=O
InChI IdentifierInChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10)
InChI KeyPHENTZNALBMCQD-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentUreas
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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046 map00240
Beta Ureidopropionase DeficiencySMP00172 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility46.1 g/LALOGPS
logP-0.86ALOGPS
logP-0.88ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.4 m³·mol⁻¹ChemAxon
Polarizability13.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0304156
FooDB IDFDB030465
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID3-UREIDO-ISOBUTYRATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID141172
ChEBI ID1670
PubChem Compound IDNot Available
Kegg Compound IDC05100
YMDB IDNot Available
ECMDB IDECMDB02031
References
Synthesis ReferenceEvans, W. R.; Tsai, Chi Shiun; Axelrod, Bernard. Origin of b-aminoisobutyric acid in iris. Nature (London, United Kingdom) (1961), 190 809.
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11675655