ECMDB: Ureidosuccinic acid (ECMDB00828) (M2MDB000189)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (1103)

Record Information

Version

2.0

Creation Date

2012-05-31 13:01:23 -0600

Update Date

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

Secondary Accession Numbers

ECMDB00828

Identification

Name:

Ureidosuccinic acid

Description

Ureidosuccinic acid is an intermediary product in pyrimidine metabolism. It is generated by the action of dihydroorotase which catalyzes the following reaction: 4,5-Dihydroorotic acid + Water <=> Ureidosuccinic acid + H+

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

2-Ureidobutanedioate
2-Ureidobutanedioic acid
Carbamoyl-Asp
Carbamoyl-aspartate
Carbamoyl-aspartic acid
Carbamoylaspartate
Carbamoylaspartic acid
Carbamyl-aspartate
Carbamyl-aspartic acid
Carbamyl-L-aspartate
Carbamyl-L-aspartic acid
Carbamylaspartate
Carbamylaspartic acid
Carbamyul-aspartate
Carbamyul-aspartic acid
Carbamyul-L-aspartate
Carbamyul-L-aspartic acid
L-N-Carbamoylaspartate
L-N-Carbamoylaspartic acid
L-Ureidosuccinate
L-Ureidosuccinic acid
N-(Aminocarbonyl)-L-aspartate
N-(Aminocarbonyl)-L-aspartic acid
N-Carbamoyl-L-aspartate
N-Carbamoyl-L-aspartic acid
N-Carbamoyl-S-aspartate
N-Carbamoyl-S-aspartic acid
N-Carbamoylaspartate
N-Carbamoylaspartic acid
NCD
Ureidosuccinate

Chemical Formula:

C₅H₈N₂O₅

Weight:

Average: 176.1274
Monoisotopic: 176.043321376

InChI Key:

HLKXYZVTANABHZ-REOHCLBHSA-N

InChI:

InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1

CAS number:

13184-27-5

IUPAC Name:

(2S)-2-(carbamoylamino)butanedioic acid

Traditional IUPAC Name:

carbamylaspartic acid

SMILES:

NC(=O)N[C@@H](CC(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Isourea
Carboximidamide
Carboxylic acid
Carboximidic acid derivative
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-aspartic acid derivative (CHEBI:15859 )
N-carbamoyl-L-amino acid (CHEBI:15859 )
N-carbamoylaspartic acid (CHEBI:15859 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

174 - 175 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	3.7 mg/mL [BEILSTEIN]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	21.3 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.7	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.65 m³·mol⁻¹	ChemAxon
Polarizability	14.72 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:

SMPDB Pathways:

Pyrimidine metabolism

PW000942

KEGG Pathways:

Alanine, aspartate and glutamate metabolism ec00250
Metabolic pathways eco01100
Pyrimidine metabolism ec00240

EcoCyc Pathways:

uridine-5'-phosphate biosynthesis PWY-5686

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
590± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
90± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
27± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
562± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f89-3940000000-f6b458a8d8c1bb66550a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-03di-1910000000-8a8dd39c35aa7c99f81a	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0920000000-cdbae9a5c80fb0023f8e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f89-3940000000-f6b458a8d8c1bb66550a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-1910000000-8a8dd39c35aa7c99f81a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-9600000000-c3f9041273a7b07c96ad	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9661000000-59d277eae56bc52aa7fa	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 (TMS_1_1) - 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 (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-2900000000-8579bc85efea27463b1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-bfd715a5dec069d32aea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-17769f0943f627a57c64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0059-0900000000-d1e136c596eda61fdad6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-1900000000-d9c4b6edb79ec7db500c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9500000000-8a0f02bbd32fdd0af067	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000i-9100000000-c1e7be64cc9ef25c1291	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d90115a5ff29ff776135	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-0900000000-d1e136c596eda61fdad6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1900000000-d9c4b6edb79ec7db500c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9500000000-ec02387ba0107a9f05cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-c1e7be64cc9ef25c1291	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d90115a5ff29ff776135	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001r-3900000000-6d42697f12c0ea7cb5ca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9600000000-29b7d3e00a4f3a870861	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004r-9300000000-e33705943fe244cfa023	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-9400000000-89114ed1862c7416a016	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-1900000000-e642a1d611b0cd263a5b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0310-8900000000-0ed6a7e85a30fafb07b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9100000000-48fee59912455e39938a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001l-6900000000-9bae4efc52500be1a047	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001c-9400000000-0fc35cb79f71cc7fbdf1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-27e270ecc918b43d4a41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02a9-7900000000-58b14b371a249024f2f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9300000000-1c5b264ddc49bbfb87f1	View in MoNA
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
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
van Kuilenburg AB, van Lenthe H, Loffler M, van Gennip AH: Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clin Chem. 2004 Nov;50(11):2117-24. Epub 2004 Sep 16. Pubmed: 15375016

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	15859
HMDB ID	HMDB00828
Pubchem Compound ID	93072
Kegg ID	C00438
ChemSpider ID	84022
Wikipedia	Carbamoyl_aspartic_acid
BioCyc ID	CARBAMYUL-L-ASPARTATE
EcoCyc ID	CARBAMYUL-L-ASPARTATE
Ligand Expo	NCD

Enzymes

Protein Details

1. Dihydroorotase

General function:: Involved in hydrolase activity
Specific function:: (S)-dihydroorotate + H(2)O = N-carbamoyl-L- aspartate
Gene Name:: pyrC
Uniprot ID:: P05020
Molecular weight:: 38827

Reactions

(S)-dihydroorotate + H(2)O = N-carbamoyl-L-aspartate.

Protein Details

2. Aspartate carbamoyltransferase catalytic chain

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate
Gene Name:: pyrB
Uniprot ID:: P0A786
Molecular weight:: 34427

Reactions

Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate.

Protein Details

3. Aspartate carbamoyltransferase regulatory chain

General function:: Involved in 'de novo' pyrimidine base biosynthetic process
Specific function:: Involved in allosteric regulation of aspartate carbamoyltransferase
Gene Name:: pyrI
Uniprot ID:: P0A7F3
Molecular weight:: 17121

Ureidosuccinic acid (ECMDB00828) (M2MDB000189)

Structure for #<Compound:0xa8fba628>

Enzymes

Reactions

Reactions