Showing Compound Card for Ureidoisobutyric acid (CDB004933)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:51:58 UTC
Updated at2020-11-18 16:39:02 UTC
CannabisDB IDCDB004933
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameUreidoisobutyric acid
DescriptionUreidoisobutyric acid, also known as ureidoisobutyrate or beta-uba, 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. Ureidoisobutyric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, ureidoisobutyric acid participates in a number of enzymatic reactions. In particular, ureidoisobutyric acid can be biosynthesized from dihydrothymine; which is catalyzed by the enzyme dihydropyrimidinase. In addition, ureidoisobutyric acid can be converted into ureidoisobutyric acid; which is mediated by the enzyme Beta-ureidopropionase. In humans, ureidoisobutyric acid is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Ureidoisobutyric acid, with regard to humans, has been linked to the inborn metabolic disorder beta-ureidopropionase deficiency. Ureidoisobutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
UreidoisobutyrateGenerator
(2S)-3-[(C-Hydroxycarbonimidoyl)amino]-2-methylpropanoateHMDB
(2S)-3-(Carbamoylamino)-2-methylpropanoic acidHMDB
(2S)-3-(Carbamoylamino)-2-methylpropionic acidHMDB
3-((Aminocarbonyl)amino)-2-methylpropanoic acidHMDB
3-((Aminocarbonyl)amino)-2-methylpropionic acidHMDB
3-UreidoisobutyrateHMDB
3-[(Aminocarbonyl)amino]-2-methylpropanoic acidHMDB
3-[(Aminocarbonyl)amino]-2-methylpropionic acidHMDB
beta-UBAHMDB
beta-Ureidoisobutyric acidHMDB
Β-ubaHMDB
Β-ureidoisobutyric acidHMDB
Chemical FormulaC5H10N2O3
Average Molecular Weight146.14
Monoisotopic Molecular Weight146.0691
IUPAC Name(2S)-3-(carbamoylamino)-2-methylpropanoic acid
Traditional Name(2S)-3-(carbamoylamino)-2-methylpropanoic acid
CAS Registry Number19140-82-0
SMILES
C[C@@H](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)/t3-/m0/s1
InChI KeyPHENTZNALBMCQD-VKHMYHEASA-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
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability13.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSUreidoisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-8900000000-51286b64a41bad89fd802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gi-9100000000-835c9b02eecbd89baac82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-40f2b4e3a071943603ee2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-9dfc177176195ee471922021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-0f56471f86b7f22306732021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-60a7db0ec3c9213e93472021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
DihydropyrimidinaseDPYS8q22Q14117 details
Beta-ureidopropionaseUPB122q11.2Q9UBR1 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
DihydropyrimidinaseDPYS8q22Q14117 details
Beta-ureidopropionaseUPB122q11.2Q9UBR1 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002031
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022808
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05100
BioCyc ID3-UREIDO-ISOBUTYRATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88558720
PDB IDURQ
ChEBI IDNot Available
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dihydropyrimidinase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
Gene Name:
DPYS
Uniprot ID:
Q14117
Molecular weight:
56629.36
Enzyme Details
2. Beta-ureidopropionase
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:
Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:
UPB1
Uniprot ID:
Q9UBR1
Molecular weight:
43165.705