Human Metabolome Database: Showing metabocard for Ureidosuccinic acid (HMDB0000828)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-02-26 21:22:39 UTC

HMDB ID

HMDB0000828

Secondary Accession Numbers

HMDB00828

Metabolite Identification

Common Name

Ureidosuccinic acid

Description

Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, 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. Ureidosuccinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ureidosuccinic acid exists in all living species, ranging from bacteria to humans. ureidosuccinic acid can be biosynthesized from carbamoyl phosphate and L-aspartic acid through the action of the enzyme cad protein. In humans, ureidosuccinic acid is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Ureidosuccinic acid has been detected, but not quantified in, several different foods, such as pigeon pea, bog bilberries, yardlong beans, carobs, and lemon balms. This could make ureidosuccinic acid a potential biomarker for the consumption of these foods. The L-enantiomer N-carbamoylaspartic acid.

Structure

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

Synonyms

Value	Source
Carbamyl-L-aspartic acid	ChEBI
L-Ureidosuccinic acid	ChEBI
N-(Aminocarbonyl)-L-aspartic acid	ChEBI
N-Carbamoyl-L-aspartate	ChEBI
N-Carbamoyl-S-aspartic acid	ChEBI
Carbamyl-L-aspartate	Generator
L-Ureidosuccinate	Generator
N-(Aminocarbonyl)-L-aspartate	Generator
N-Carbamoyl-L-aspartic acid	Generator
N-Carbamoyl-S-aspartate	Generator
Ureidosuccinate	Generator
2-Ureidobutanedioate	HMDB
2-Ureidobutanedioic acid	HMDB
Carbamoylaspartic acid	HMDB
Carbamylaspartic acid	HMDB
L-N-Carbamoylaspartic acid	HMDB
N-Carbamoylaspartate	HMDB
N-Carbamoylaspartic acid	HMDB
NCD	HMDB
Carbamyl-DL-aspartate	HMDB
Ureidosuccinic acid, (D)-isomer	HMDB
Ureidosuccinic acid, maganeese (+2), (1:1) salt	HMDB
Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer	HMDB
N-Carbamoyl-D-aspartic acid	HMDB
Ureidosuccinic acid, (L)-isomer	HMDB
Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer	HMDB

Chemical Formula

C₅H₈N₂O₅

Average Molecular Weight

176.1274

Monoisotopic Molecular Weight

176.043321376

IUPAC Name

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

Traditional Name

carbamylaspartic acid

CAS Registry Number

13184-27-5

SMILES

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

InChI Identifier

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

InChI Key

HLKXYZVTANABHZ-REOHCLBHSA-N

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	174 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.7 mg/mL	Not Available
LogP	Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f89-3940000000-f6b458a8d8c1bb66550a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-03di-1910000000-8a8dd39c35aa7c99f81a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0920000000-cdbae9a5c80fb0023f8e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f89-3940000000-f6b458a8d8c1bb66550a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-1910000000-8a8dd39c35aa7c99f81a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-9600000000-c3f9041273a7b07c96ad	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9661000000-59d277eae56bc52aa7fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-2900000000-8579bc85efea27463b1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-bfd715a5dec069d32aea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-17769f0943f627a57c64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0059-0900000000-d1e136c596eda61fdad6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-1900000000-d9c4b6edb79ec7db500c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9500000000-8a0f02bbd32fdd0af067	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000i-9100000000-c1e7be64cc9ef25c1291	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d90115a5ff29ff776135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-0900000000-d1e136c596eda61fdad6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1900000000-d9c4b6edb79ec7db500c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9500000000-ec02387ba0107a9f05cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-c1e7be64cc9ef25c1291	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d90115a5ff29ff776135	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-1900000000-e642a1d611b0cd263a5b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0310-8900000000-0ed6a7e85a30fafb07b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9100000000-48fee59912455e39938a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001l-6900000000-9bae4efc52500be1a047	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001c-9400000000-0fc35cb79f71cc7fbdf1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-27e270ecc918b43d4a41	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Prostate Tissue
Saliva

Tissue Locations

Prostate

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyrimidine Metabolism
Aspartate Metabolism
Canavan Disease		Not Available
Hypoacetylaspartia		Not Available
Beta Ureidopropionase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Prostate Tissue	Detected and Quantified	0.5 (0.0-1.0) umol/g tissue	Adult (>18 years old)	Both	Prostate Cancer	19212411	details

Associated Disorders and Diseases

Disease References

Prostate cancer

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. doi: 10.1038/nature07762. [PubMed:19212411 ]

Associated OMIM IDs

176807 (Prostate cancer)

External Links

DrugBank ID

DB04252

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

CARBAMYUL-L-ASPARTATE

BiGG ID

34984

Wikipedia Link

Carbamoyl_aspartic_acid

METLIN ID

5791

PubChem Compound

93072

PDB ID

Not Available

ChEBI ID

15859

Food Biomarker Ontology

Not Available

VMH ID

CBASP

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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. doi: 10.1038/nature07762. [PubMed:19212411 ]

Enzymes

Enzyme Details

1. Aspartate--tRNA ligase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: Catalyzes the specific attachment of an amino acid to its cognate tRNA in a 2 step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of the tRNA.
Gene Name:: DARS
Uniprot ID:: P14868
Molecular weight:: 57135.8

Enzyme Details

2. Glutamate decarboxylase 1

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the production of GABA.
Gene Name:: GAD1
Uniprot ID:: Q99259
Molecular weight:: 66896.065

Enzyme Details

3. CAD protein

General function:: Involved in hydrolase activity
Specific function:: This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:: CAD
Uniprot ID:: P27708
Molecular weight:: 242981.73

Reactions

Carbamoyl phosphate + L-Aspartic acid → Phosphate + Ureidosuccinic acid	details
L-Dihydroorotic acid + Water → Ureidosuccinic acid	details

Showing metabocard for Ureidosuccinic acid (HMDB0000828)

Structure for HMDB0000828 (Ureidosuccinic acid)

Enzymes

Reactions