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Showing metabocard for Ureidosuccinic acid (HMDB0000828)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:39 UTC
HMDB IDHMDB0000828
Secondary Accession Numbers
  • HMDB00828
Metabolite Identification
Common NameUreidosuccinic acid
DescriptionUreidosuccinic 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
Data?1582752159
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Carbamyl-L-aspartic acidChEBI
L-Ureidosuccinic acidChEBI
N-(Aminocarbonyl)-L-aspartic acidChEBI
N-Carbamoyl-L-aspartateChEBI
N-Carbamoyl-S-aspartic acidChEBI
Carbamyl-L-aspartateGenerator
L-UreidosuccinateGenerator
N-(Aminocarbonyl)-L-aspartateGenerator
N-Carbamoyl-L-aspartic acidGenerator
N-Carbamoyl-S-aspartateGenerator
UreidosuccinateGenerator
2-UreidobutanedioateHMDB
2-Ureidobutanedioic acidHMDB
Carbamoylaspartic acidHMDB
Carbamylaspartic acidHMDB
L-N-Carbamoylaspartic acidHMDB
N-CarbamoylaspartateHMDB
N-Carbamoylaspartic acidHMDB
NCDHMDB
Carbamyl-DL-aspartateHMDB
Ureidosuccinic acid, (D)-isomerHMDB
Ureidosuccinic acid, maganeese (+2), (1:1) saltHMDB
Ureidosuccinic acid, zinc (1:1) salt, (L)-isomerHMDB
N-Carbamoyl-D-aspartic acidHMDB
Ureidosuccinic acid, (L)-isomerHMDB
Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomerHMDB
Chemical FormulaC5H8N2O5
Average Molecular Weight176.1274
Monoisotopic Molecular Weight176.043321376
IUPAC Name(2S)-2-(carbamoylamino)butanedioic acid
Traditional Namecarbamylaspartic acid
CAS Registry Number13184-27-5
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 KeyHLKXYZVTANABHZ-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.7 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility21.3 g/LALOGPS
logP-1.1ALOGPS
logP-1.7ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability14.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f89-3940000000-f6b458a8d8c1bb66550aSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03di-1910000000-8a8dd39c35aa7c99f81aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0920000000-cdbae9a5c80fb0023f8eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f89-3940000000-f6b458a8d8c1bb66550aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1910000000-8a8dd39c35aa7c99f81aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0016-9600000000-c3f9041273a7b07c96adSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9661000000-59d277eae56bc52aa7faSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-2900000000-8579bc85efea27463b1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-bfd715a5dec069d32aeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-17769f0943f627a57c64Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0059-0900000000-d1e136c596eda61fdad6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-d9c4b6edb79ec7db500cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9500000000-8a0f02bbd32fdd0af067Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-c1e7be64cc9ef25c1291Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d90115a5ff29ff776135Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-0900000000-d1e136c596eda61fdad6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-d9c4b6edb79ec7db500cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-ec02387ba0107a9f05cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-c1e7be64cc9ef25c1291Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d90115a5ff29ff776135Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057i-1900000000-e642a1d611b0cd263a5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0310-8900000000-0ed6a7e85a30fafb07b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9100000000-48fee59912455e39938aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-6900000000-9bae4efc52500be1a047Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001c-9400000000-0fc35cb79f71cc7fbdf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-27e270ecc918b43d4a41Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Prostate Tissue
  • Saliva
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)Both
Prostate Cancer		 details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. 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
DrugBank IDDB04252
Phenol Explorer Compound IDNot Available
FooDB IDFDB031033
KNApSAcK IDC00007265
Chemspider ID84022
KEGG Compound IDC00438
BioCyc IDCARBAMYUL-L-ASPARTATE
BiGG ID34984
Wikipedia LinkCarbamoyl_aspartic_acid
METLIN ID5791
PubChem Compound93072
PDB IDNot Available
ChEBI ID15859
Food Biomarker OntologyNot Available
VMH IDCBASP
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 aciddetails
L-Dihydroorotic acid + Water → Ureidosuccinic aciddetails