Livestock Metabolome Database: Showing metabocard for Ureidopropionic acid (LMDB00008)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:22:15 UTC

Update Date

2016-07-20 20:48:21 UTC

Lmdb

LMDB00008

Secondary Accession Numbers

None

Metabolite Identification

Common 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

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected and Quantified	347 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	615 umol/mmol creatinine	Not Available	Porcine	23741447	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0062812

FooDB ID

FDB021879

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

3-UREIDO-PROPIONATE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

3-Ureidopropionic_acid

Chemspider ID

109

ChEBI ID

18261

PubChem Compound ID

Not Available

Kegg Compound ID

C02642

YMDB ID

Not Available

ECMDB ID

ECMDB00026

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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. [11675655 ]

Showing metabocard for Ureidopropionic acid (LMDB00008)

Structure for LMDB00008 (Ureidopropionic acid)