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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:28 UTC

HMDB ID

HMDB0000026

Secondary Accession Numbers

HMDB00026
HMDB0062812
HMDB62812

Metabolite Identification

Common Name

Ureidopropionic acid

Description

Ureidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-beta-alanine, 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. Ureidopropionic acid is an intermediate in the metabolism of uracil. More specifically, it is a breakdown product of dihydrouracil and is produced by the enzyme dihydropyrimidase. It is further decomposed into beta-alanine via the enzyme beta-ureidopropionase. Ureidopropionic acid is essentially a urea derivative of beta-alanine. High levels of ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency (PMID: 11675655 ). Enzyme deficiencies in pyrimidine metabolism are associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil. Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheat, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-[(Aminocarbonyl)amino]propanoic acid	ChEBI
3-Ureidopropanoate	ChEBI
3-Ureidopropanoic acid	ChEBI
3-Ureidopropionate	ChEBI
3-Ureidopropionic acid	ChEBI
beta-Ureidopropionic acid	ChEBI
N-(AMINOCARBONYL)-BETA-alanine	ChEBI
Ureidopropanoic acid	ChEBI
N-Carbamoyl-beta-alanine	Kegg
3-[(Aminocarbonyl)amino]propanoate	Generator
b-Ureidopropionate	Generator
b-Ureidopropionic acid	Generator
beta-Ureidopropionate	Generator
Β-ureidopropionate	Generator
Β-ureidopropionic acid	Generator
N-(AMINOCARBONYL)-b-alanine	Generator
N-(AMINOCARBONYL)-β-alanine	Generator
Ureidopropanoate	Generator
N-Carbamoyl-b-alanine	Generator
N-Carbamoyl-β-alanine	Generator
Ureidopropionate	Generator
3-(carbamoylamino)Propanoate	HMDB
3-(carbamoylamino)Propanoic acid	HMDB
3-ureido-Propionate	HMDB
Carbamoyl-b-ala-OH	HMDB
Carbamoyl-beta-ala-OH	HMDB
N-(Aminocarbonyl)-'b-alanine	HMDB
N-Carbamyl-b-alanine	HMDB
N-Carbamyl-beta-alanine	HMDB
Ion(-1) OF N-carbamoyl-beta-alanine	MeSH, HMDB
Carbamoyl-beta-alanine	HMDB
Carbamoyl-β-alanine	HMDB
Carbamyl beta-alanine	HMDB
Carbamyl β-alanine	HMDB
beta-Ureidopropanoic acid	HMDB
β-Ureidopropanoic acid	HMDB

Chemical Formula

C₄H₈N₂O₃

Average Molecular Weight

132.1179

Monoisotopic Molecular Weight

132.053492132

IUPAC Name

3-(carbamoylamino)propanoic acid

Traditional Name

ureidopropionic acid

CAS Registry Number

462-88-4

SMILES

NC(=O)NCCC(O)=O

InChI Identifier

InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)

InChI Key

JSJWCHRYRHKBBW-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

beta-alanine derivative (CHEBI:18261 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	20.9 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	52.7 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-1.4	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-2	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	28.82 m³·mol⁻¹	ChemAxon
Polarizability	12.07 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
DarkChem	[M+H]+	128.114	31661259
DarkChem	[M+H]+	128.114	31661259
DarkChem	[M-H]-	122.326	31661259
DarkChem	[M-H]-	122.326	31661259
AllCCS	[M+H]+	130.82	32859911
AllCCS	[M-H]-	126.421	32859911
DeepCCS	[M+H]+	128.636	30932474
DeepCCS	[M-H]-	125.717	30932474
DeepCCS	[M-2H]-	162.136	30932474
DeepCCS	[M+Na]+	137.2	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.7	32859911
AllCCS	[M+NH4]+	134.6	32859911
AllCCS	[M+Na]+	135.7	32859911
AllCCS	[M-H]-	126.4	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.5 minutes	32390414
Predicted by Siyang on May 30, 2022	8.6447 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	371.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	400.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	43.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	205.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	221.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	860.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	555.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	37.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	649.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	757.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	529.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	370.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ureidopropionic acid	NC(=O)NCCC(O)=O	2311.6	Standard polar	33892256
Ureidopropionic acid	NC(=O)NCCC(O)=O	1450.7	Standard non polar	33892256
Ureidopropionic acid	NC(=O)NCCC(O)=O	1734.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ureidopropionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(N)=O	1590.3	Semi standard non polar	33892256
Ureidopropionic acid,1TMS,isomer #2	C[Si](C)(C)NC(=O)NCCC(=O)O	1614.3	Semi standard non polar	33892256
Ureidopropionic acid,1TMS,isomer #3	C[Si](C)(C)N(CCC(=O)O)C(N)=O	1609.2	Semi standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #1	C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C	1675.0	Semi standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #1	C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C	1475.1	Standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #1	C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C	2282.5	Standard polar	33892256
Ureidopropionic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C	1585.2	Semi standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C	1559.0	Standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C	2393.3	Standard polar	33892256
Ureidopropionic acid,2TMS,isomer #3	C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C	1727.3	Semi standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #3	C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C	1609.8	Standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #3	C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C	2317.0	Standard polar	33892256
Ureidopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C	1701.1	Semi standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C	1661.7	Standard non polar	33892256
Ureidopropionic acid,2TMS,isomer #4	C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C	2219.5	Standard polar	33892256
Ureidopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	1719.3	Semi standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	1597.6	Standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	1982.7	Standard polar	33892256
Ureidopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1671.7	Semi standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1619.3	Standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1935.4	Standard polar	33892256
Ureidopropionic acid,3TMS,isomer #3	C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1745.9	Semi standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #3	C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1787.0	Standard non polar	33892256
Ureidopropionic acid,3TMS,isomer #3	C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1926.1	Standard polar	33892256
Ureidopropionic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1756.3	Semi standard non polar	33892256
Ureidopropionic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1769.4	Standard non polar	33892256
Ureidopropionic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1725.3	Standard polar	33892256
Ureidopropionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(N)=O	1832.7	Semi standard non polar	33892256
Ureidopropionic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O	1867.0	Semi standard non polar	33892256
Ureidopropionic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(N)=O	1813.5	Semi standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C	2114.6	Semi standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C	1865.0	Standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C	2284.7	Standard polar	33892256
Ureidopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C	2029.9	Semi standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C	1970.3	Standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C	2477.1	Standard polar	33892256
Ureidopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C	2156.4	Semi standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C	1999.9	Standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C	2282.3	Standard polar	33892256
Ureidopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C	2138.6	Semi standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C	2002.2	Standard non polar	33892256
Ureidopropionic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C	2263.9	Standard polar	33892256
Ureidopropionic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2368.8	Semi standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2207.1	Standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2227.0	Standard polar	33892256
Ureidopropionic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2333.2	Semi standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2193.4	Standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2242.2	Standard polar	33892256
Ureidopropionic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2387.9	Semi standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2311.4	Standard non polar	33892256
Ureidopropionic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2223.3	Standard polar	33892256
Ureidopropionic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2615.6	Semi standard non polar	33892256
Ureidopropionic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2520.6	Standard non polar	33892256
Ureidopropionic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2209.5	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
beta-Alanine metabolism	Not Available
Pyrimidine metabolism	Not Available
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 0.5 uM	Children (1-13 years old)	Not Specified	Normal	17383919	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	2.23 (1.48 - 2.81) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16513432	details
Urine	Detected and Quantified	2.09 (1.23–4.80) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12798197	details
Urine	Detected and Quantified	0.88 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12798197	details
Urine	Detected and Quantified	<3.2 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.5 (0.0-1.0) uM	Children (1-13 years old)	Both	Dihydropyrimidinase deficiency	17383919	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Dihydropyrimidinase deficiency
van Kuilenburg AB, Meijer J, Dobritzsch D, Meinsma R, Duran M, Lohkamp B, Zoetekouw L, Abeling NG, van Tinteren HL, Bosch AM: Clinical, biochemical and genetic findings in two siblings with a dihydropyrimidinase deficiency. Mol Genet Metab. 2007 Jun;91(2):157-64. Epub 2007 Mar 26. [PubMed:17383919 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

222748 (Dihydropyrimidinase deficiency)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021879

KNApSAcK ID

Not Available

Chemspider ID

109

KEGG Compound ID

C02642

BioCyc ID

3-UREIDO-PROPIONATE

BiGG ID

Not Available

Wikipedia Link

3-Ureidopropionic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18261

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

w-Ureido carboxylic acids. (1962), 3 pp. GB 913713 19621228 CAN 58:72975 AN 1963:72975

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Moolenaar SH, Gohlich-Ratmann G, Engelke UF, Spraul M, Humpfer E, Dvortsak P, Voit T, Hoffmann GF, Brautigam C, van Kuilenburg AB, van Gennip A, Vreken P, Wevers RA: beta-Ureidopropionase deficiency: a novel inborn error of metabolism discovered using NMR spectroscopy on urine. Magn Reson Med. 2001 Nov;46(5):1014-7. [PubMed:11675655 ]
Sparidans RW, Bosch TM, Jorger M, Schellens JH, Beijnen JH: Liquid chromatography-tandem mass spectrometric assay for the analysis of uracil, 5,6-dihydrouracil and beta-ureidopropionic acid in urine for the measurement of the activities of the pyrimidine catabolic enzymes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jul 24;839(1-2):45-53. Epub 2006 Feb 28. [PubMed:16513432 ]
Ito S, Kawamura T, Inada M, Inoue Y, Hirao Y, Koga T, Kunizaki J, Shimizu T, Sato H: Physiologically based pharmacokinetic modelling of the three-step metabolism of pyrimidine using C-uracil as an in vivo probe. Br J Clin Pharmacol. 2005 Dec;60(6):584-93. [PubMed:16305582 ]
Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. [PubMed:12798197 ]
Malet-Martino MC, Armand JP, Lopez A, Bernadou J, Beteille JP, Bon M, Martino R: Evidence for the importance of 5'-deoxy-5-fluorouridine catabolism in humans from 19F nuclear magnetic resonance spectrometry. Cancer Res. 1986 Apr;46(4 Pt 2):2105-12. [PubMed:2936452 ]
Desmoulin F, Gilard V, Malet-Martino M, Martino R: Metabolism of capecitabine, an oral fluorouracil prodrug: (19)F NMR studies in animal models and human urine. Drug Metab Dispos. 2002 Nov;30(11):1221-9. [PubMed:12386128 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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

Reactions

Dihydrouracil + Water → Ureidopropionic acid	details

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

Reactions

Ureidopropionic acid + Water → beta-Alanine + CO(2) + Ammonia	details
Ureidopropionic acid + Water → beta-Alanine + Carbon dioxide + Ammonia	details

References

Moolenaar SH, Gohlich-Ratmann G, Engelke UF, Spraul M, Humpfer E, Dvortsak P, Voit T, Hoffmann GF, Brautigam C, van Kuilenburg AB, van Gennip A, Vreken P, Wevers RA: beta-Ureidopropionase deficiency: a novel inborn error of metabolism discovered using NMR spectroscopy on urine. Magn Reson Med. 2001 Nov;46(5):1014-7. [PubMed:11675655 ]

Enzyme Details

3. Dihydropyrimidinase-related protein 3

General function:: Involved in hydrolase activity
Specific function:: Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:: DPYSL3
Uniprot ID:: Q14195
Molecular weight:: 61962.8

Enzyme Details

4. Dihydropyrimidinase-related protein 2

General function:: Nucleotide transport and metabolism
Specific function:: Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:: DPYSL2
Uniprot ID:: Q16555
Molecular weight:: 62293.1

Showing metabocard for Ureidopropionic acid (HMDB0000026)

MOL for HMDB0000026 (Ureidopropionic acid)

3D MOL for HMDB0000026 (Ureidopropionic acid)

3D SDF for HMDB0000026 (Ureidopropionic acid)

3D-SDF for HMDB0000026 (Ureidopropionic acid)

PDB for HMDB0000026 (Ureidopropionic acid)

3D PDB for HMDB0000026 (Ureidopropionic acid)

SMILES for HMDB0000026 (Ureidopropionic acid)

INCHI for HMDB0000026 (Ureidopropionic acid)

Structure for HMDB0000026 (Ureidopropionic acid)

3D Structure for HMDB0000026 (Ureidopropionic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

References