Showing NP-Card for Ureidosuccinic acid (NP0000333)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:41:26 UTC
NP-MRD IDNP0000333
Secondary Accession NumbersNone
Natural Product 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 acids and derivatives. Aspartic acids 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 also classified as a carbamate derivative. It is a solid that is soluble in water. Ureidosuccinic acid exists in all living species, ranging from bacteria to plants to humans. Ureidosuccinic acid can be biosynthesized from carbamoyl phosphate and L-aspartic acid through the action of the enzyme known as aspartate carbamoyltransferase (ACTase) and serves as an intermediate in pyrimidine biosynthesis. In humans, a drop in the level of urinary ureidosuccinic acid is associated with bladder cancer (PMID: 25562196 ). It is also involved in the metabolic disorder called Canavan disease.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000333 (Ureidosuccinic acid)

  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0000333 (Ureidosuccinic acid)

HMDB0000828
     RDKit          3D
Ureidosuccinic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    3.0110    1.2510   -0.5389 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    0.8763    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828    1.2218    1.6276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.1093    0.0922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -0.2768    1.0714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4272    0.3712    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615    0.0008   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -1.1040   -0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600    0.8485   -1.6348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -1.7402    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5388   -2.4708    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -2.3574    2.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    0.5727   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900    2.2390   -0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -0.1757   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.1437    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198    1.4691    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216    0.0237    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    1.8237   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -2.8261    1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  1
  6 17  1  0
  6 18  1  0
  9 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000333 (Ureidosuccinic acid)

  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000333

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C5H8N2O5

> <MOLECULAR_WEIGHT>
176.1274

> <EXACT_MASS>
176.043321376

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.723969618976081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(carbamoylamino)butanedioic acid

> <ALOGPS_LOGP>
-1.12

> <JCHEM_LOGP>
-1.7352221553333331

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.2526016307709105

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.333225520739885

> <JCHEM_PKA_STRONGEST_BASIC>
-2.589637248709309

> <JCHEM_POLAR_SURFACE_AREA>
129.72000000000003

> <JCHEM_REFRACTIVITY>
34.653200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbamylaspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000333 (Ureidosuccinic acid)

HMDB0000828
     RDKit          3D
Ureidosuccinic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    3.0110    1.2510   -0.5389 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    0.8763    0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828    1.2218    1.6276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.1093    0.0922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -0.2768    1.0714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4272    0.3712    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615    0.0008   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -1.1040   -0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600    0.8485   -1.6348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -1.7402    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5388   -2.4708    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -2.3574    2.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    0.5727   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900    2.2390   -0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -0.1757   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.1437    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198    1.4691    0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216    0.0237    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836    1.8237   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -2.8261    1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  1
  6 17  1  0
  6 18  1  0
  9 19  1  0
 12 20  1  0
M  END
Download

PDB for NP0000333 (Ureidosuccinic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       3.286   3.437   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.954   3.437   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.954   0.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000333 (Ureidosuccinic acid)

COMPND    HMDB0000828
HETATM    1  N1  UNL     1       3.011   1.251  -0.539  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.046   0.876   0.422  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.183   1.222   1.628  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.898   0.109   0.092  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.093  -0.277   1.071  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.427   0.371   0.777  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.961   0.001  -0.545  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.529  -1.104  -0.722  1.00  0.00           O  
HETATM    9  O3  UNL     1      -1.860   0.849  -1.635  1.00  0.00           O  
HETATM   10  C5  UNL     1      -0.178  -1.740   1.138  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.539  -2.471   0.416  1.00  0.00           O  
HETATM   12  O5  UNL     1      -1.072  -2.357   2.018  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.703   0.573  -0.943  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.090   2.239  -0.906  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.790  -0.176  -0.913  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.247   0.144   2.054  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.320   1.469   0.874  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.122   0.024   1.592  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.084   1.824  -1.601  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.860  -2.826   1.569  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   10   16
CONECT    6    7   17   18
CONECT    7    8    8    9
CONECT    9   19
CONECT   10   11   11   12
CONECT   12   20
END
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SMILES for NP0000333 (Ureidosuccinic acid)

NC(=O)N[C@@H](CC(O)=O)C(O)=O
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INCHI for NP0000333 (Ureidosuccinic acid)

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
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View in JSmol
Synonyms
Chemical FormulaC5H8N2O5
Average Mass176.1274 Da
Monoisotopic Mass176.04332 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-07View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
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
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
Good Scents IDNot Available
References
General References
  1. Shen C, Sun Z, Chen D, Su X, Jiang J, Li G, Lin B, Yan J: Developing urinary metabolomic signatures as early bladder cancer diagnostic markers. OMICS. 2015 Jan;19(1):1-11. doi: 10.1089/omi.2014.0116. [PubMed:25562196 ]