ECMDB: Ureidopropionic acid (ECMDB00026) (M2MDB000006)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (141)

Record Information

Version

2.0

Creation Date

2012-05-31 09:55:28 -0600

Update Date

2015-09-13 12:56:05 -0600

Secondary Accession Numbers

ECMDB00026

Identification

Name:

Ureidopropionic acid

Description

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 to 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-ureidopropionate
β-ureidopropionic acid
3-(Carbamoylamino)propanoate
3-(Carbamoylamino)propanoic acid
3-Ureido-propionate
3-Ureido-propionic acid
3-Ureidopropanoate
3-Ureidopropanoic acid
3-Ureidopropionate
3-Ureidopropionic acid
N-carbamoyl-β-alanine
b-Ureidopropionate
b-Ureidopropionic acid
Beta-Ureidopropionate
Beta-Ureidopropionic acid
Carbamoyl-b-Ala-OH
Carbamoyl-beta-Ala-OH
Carbamoyl-β-ala-OH
N-(Aminocarbonyl)-'b-Alanine
N-(Aminocarbonyl)-b-alanine
N-(Aminocarbonyl)-beta-Alanine
N-(Aminocarbonyl)-β-alanine
n-Carbamoyl-β-alanine
N-Carbamoyl-b-alanine
N-Carbamoyl-beta-alanine
N-Carbamoyl-β-alanine
N-Carbamyl-b-alanine
N-Carbamyl-beta-alanine
N-Carbamyl-β-alanine
Ureidopropionate
Ureidopropionic acid
β-Ureidopropionate
β-Ureidopropionic acid

Chemical Formula:

C₄H₈N₂O₃

Weight:

Average: 132.1179
Monoisotopic: 132.053492132

InChI Key:

JSJWCHRYRHKBBW-UHFFFAOYSA-N

InChI:

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

CAS number:

462-88-4

IUPAC Name:

3-(carbamoylamino)propanoic acid

Traditional IUPAC Name:

ureidopropionic acid

SMILES:

NC(=O)NCCC(O)=O

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 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

170 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	20.9 mg/mL [BEILSTEIN]	PhysProp

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Dihydrouracil + Water <> Ureidopropionic acid

SMPDB Pathways:

Pantothenate and CoA biosynthesis	PW000828
Pyrimidine metabolism	PW000942
beta-Alanine metabolism	PW000896

KEGG Pathways:

Drug metabolism - other enzymes ec00983
Metabolic pathways eco01100
Pantothenate and CoA biosynthesis ec00770
Pyrimidine metabolism ec00240
beta-Alanine metabolism ec00410

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-3910000000-bbd51b3bb30ff8d230d3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00n0-5900000000-00dc280a63401c96ec2a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-2930000000-fcdce5cf4a20023c403a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0hr0-2900000000-8a898fc59206b3f30a13	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-3910000000-bbd51b3bb30ff8d230d3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00n0-5900000000-00dc280a63401c96ec2a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-2930000000-fcdce5cf4a20023c403a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0hr0-2900000000-8a898fc59206b3f30a13	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udj-1910000000-83ab1eb4328f8caae993	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0v01-0900000000-aeacd84d8e0e91418232	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-f7cdf5fc49adf0b5e726	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9300000000-7b12845cd5bc4d02874c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00r6-9500000000-7ea8c95e3dc6296a07e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9100000000-7b61b087fbf6c821bdd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0596-9200000000-79dfb7a1a6838745e178	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014l-8900000000-9bfe2297b9071d10d7e5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001i-2900000000-e1e9196162c1cd0606e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001r-5900000000-0e75c38978d4fd27ad1b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001r-8900000000-d71c6b65e5ea4a2b98a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0019-9600000000-995ba80b11e5e2fdbed6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9300000000-efa2833fbedc0d3bd746	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9200000000-92bf1d8bc142b2e065f4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9100000000-e52a09e58825a4f43bbb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9000000000-0a7fa362cd3cbcf81534	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-9000000000-88ef7f8836542c76d47b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-9000000000-223a7c6bd0e90d91dacf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-000i-9000000000-eefd307fa9aedb8dbaaa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-000i-9000000000-ae89b554e34311f8358b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-000i-9000000000-1cfc112d7baf56aa65ab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 9V, negative	splash10-000i-9100000000-97d06beb4575ef6147d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 9V, negative	splash10-0a4i-9000000000-08bac9ac1941233e516c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-7900000000-684d9877d084bfc7c955	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9100000000-0b6f9ea311703e9ecf13	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-9000000000-1cb23a8265b882313309	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001c-9300000000-2cec50bd5b226a288c82	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9100000000-63ecd2f9ef02c677503d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-396bc860a5f8f06ff7c5	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
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
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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
Moolenaar, S. H., Gohlich-Ratmann, G., Engelke, U. F., Spraul, M., Humpfer, E., Dvortsak, P., Voit, T., Hoffmann, G. F., Brautigam, C., van Kuilenburg, A. B., van Gennip, A., Vreken, P., Wevers, R. A. (2001). "beta-Ureidopropionase deficiency: a novel inborn error of metabolism discovered using NMR spectroscopy on urine." Magn Reson Med 46:1014-1017. Pubmed: 11675655
Patel BN, West TP. 1987. "Degradation of the pyrimidine bases uracil and thymine by Escherichia coli B." Microbios 49(199):107-13 Pubmed: 3553866
Simaga S, Kos E. 1978. "Uracil catabolism by Escherichia coli K12S." Z Naturforsch C 33(11-12):1006-8 Pubmed: 154218
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

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)

Links

External Links:

Resource	Link
CHEBI ID	18261
HMDB ID	HMDB00026
Pubchem Compound ID	111
Kegg ID	C02642
ChemSpider ID	109
Wikipedia ID	3-Ureidopropionic_acid
BioCyc ID	3-UREIDO-PROPIONATE
EcoCyc ID	3-UREIDO-PROPIONATE
Ligand Expo	URP

Enzymes

Protein Details

1. D-phenylhydantoinase

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:: Catalyzes the stereospecific hydrolysis of the cyclic amide bond of D-hydantoin derivatives with an aromatic side chains at the 5'-position. Has no activity on dihydropyrimidines. The physiological function is unknown
Gene Name:: hyuA
Uniprot ID:: Q46806
Molecular weight:: 51025

Protein Details

2. Uncharacterized oxidoreductase yeiT

General function:: Involved in oxidoreductase activity
Specific function:: Specific function unknown
Gene Name:: yeiT
Uniprot ID:: P76440
Molecular weight:: 44329

Reactions

5,6-dihydrouracil + NAD(+) = uracil + NADH.
5,6-dihydrothymine + NAD(+) = thymine + NADH.

Ureidopropionic acid (ECMDB00026) (M2MDB000006)

Structure for #<Compound:0xa184ae58>

Enzymes

Reactions