Showing Compound Card for Ureidosuccinic acid (CDB004866)

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Record Information
Version1.0
Created at2020-04-17 18:44:52 UTC
Updated at2020-11-18 16:38:53 UTC
CannabisDB IDCDB004866
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameUreidosuccinic acid
DescriptionUreidosuccinic acid, also known as carbamyl-L-aspartate or L-ureidosuccinate, 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; which is catalyzed by 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 chervils, agars, cabbages, swamp cabbages, and safflowers. This could make ureidosuccinic acid a potential biomarker for the consumption of these foods. The L-enantiomer N-carbamoylaspartic acid. Ureidosuccinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight176.13
Monoisotopic Molecular Weight176.0433
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:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSUreidosuccinic acid, 4 TMS, GC-MS Spectrumsplash10-0f89-3940000000-f6b458a8d8c1bb66550aSpectrum
GC-MSUreidosuccinic acid, 3 TMS, GC-MS Spectrumsplash10-03di-1910000000-8a8dd39c35aa7c99f81aSpectrum
GC-MSUreidosuccinic acid, non-derivatized, GC-MS Spectrumsplash10-03di-0920000000-cdbae9a5c80fb0023f8eSpectrum
GC-MSUreidosuccinic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-3940000000-f6b458a8d8c1bb66550aSpectrum
GC-MSUreidosuccinic acid, non-derivatized, GC-MS Spectrumsplash10-03di-1910000000-8a8dd39c35aa7c99f81aSpectrum
Predicted GC-MSUreidosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0016-9600000000-c3f9041273a7b07c96adSpectrum
Predicted GC-MSUreidosuccinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9661000000-59d277eae56bc52aa7faSpectrum
Predicted GC-MSUreidosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUreidosuccinic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-2900000000-8579bc85efea27463b1a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-bfd715a5dec069d32aea2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-17769f0943f627a57c642012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0059-0900000000-d1e136c596eda61fdad62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-d9c4b6edb79ec7db500c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9500000000-8a0f02bbd32fdd0af0672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-c1e7be64cc9ef25c12912012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d90115a5ff29ff7761352012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-0900000000-d1e136c596eda61fdad62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-d9c4b6edb79ec7db500c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-ec02387ba0107a9f05cb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-c1e7be64cc9ef25c12912017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d90115a5ff29ff7761352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001r-3900000000-6d42697f12c0ea7cb5ca2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9600000000-29b7d3e00a4f3a8708612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004r-9300000000-e33705943fe244cfa0232021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000i-9400000000-89114ed1862c7416a0162021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057i-1900000000-e642a1d611b0cd263a5b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0310-8900000000-0ed6a7e85a30fafb07b22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9100000000-48fee59912455e39938a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-6900000000-9bae4efc52500be1a0472016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001c-9400000000-0fc35cb79f71cc7fbdf12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-27e270ecc918b43d4a412016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02a9-7900000000-58b14b371a249024f2f72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9300000000-1c5b264ddc49bbfb87f12021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aspartate--tRNA ligase, cytoplasmicDARS2q21.3P14868 details
Glutamate decarboxylase 1GAD12q31Q99259 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
CAD proteinCAD2p22-p21P27708 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000828
DrugBank IDDB04252
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

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