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Showing NP-Card for carbamoyl aspartic acid (NP0327772)

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Record Information
Version2.0
Created at2022-09-12 10:39:30 UTC
Updated at2022-09-12 10:39:31 UTC
NP-MRD IDNP0327772
Secondary Accession NumbersNone
Natural Product Identification
Common Namecarbamoyl aspartic acid
DescriptionN-carbamoylaspartic acid, also known as 2-ureidobutanedioic acid or ureidosuccinic acid, 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. carbamoyl aspartic acid is found in Arabidopsis thaliana. carbamoyl aspartic acid was first documented in 1952 (PMID: 14920504). N-carbamoylaspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 131912) (PMID: 13831) (PMID: 13882306) (PMID: 14367323).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0327772 (carbamoyl aspartic acid)


  Mrv1652310071712352D          

 12 11  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
M  END
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3D MOL for NP0327772 (carbamoyl aspartic acid)

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3D SDF for NP0327772 (carbamoyl aspartic acid)

  Mrv1652310071712352D          

 12 11  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(NC(O)=N)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)

> <INCHI_KEY>
HLKXYZVTANABHZ-UHFFFAOYSA-N

> <FORMULA>
C5H8N2O5

> <MOLECULAR_WEIGHT>
176.128

> <EXACT_MASS>
176.043321366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.728524636216193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(carbamoylamino)butanedioic acid

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-1.7352221553333331

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.252601630770911

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.333225520739887

> <JCHEM_PKA_STRONGEST_BASIC>
-2.589637248709309

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
34.6532

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ureidosuccinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0327772 (carbamoyl aspartic acid)
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PDB for NP0327772 (carbamoyl aspartic acid)
HEADER    PROTEIN                                 07-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-OCT-17         0                                  
HETATM    1  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.875   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.206   0.770   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       8.208   0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.875  -1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.541  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    7                                                  
CONECT    3    1    8    9                                                  
CONECT    4    2   10   11                                                  
CONECT    5    6    7   12                                                  
CONECT    6    5                                                            
CONECT    7    2    5                                                       
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0327772 (carbamoyl aspartic acid)
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SMILES for NP0327772 (carbamoyl aspartic acid)
OC(=O)CC(NC(O)=N)C(O)=O
Download
INCHI for NP0327772 (carbamoyl aspartic 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)
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View in JSmol
Synonyms
ValueSource
2-Ureidobutanedioic acidChEBI
Carbamylaspartic acidChEBI
N-(Aminocarbonyl)-DL-aspartic acidChEBI
Ureidosuccinic acidChEBI
2-UreidobutanedioateGenerator
CarbamylaspartateGenerator
N-(Aminocarbonyl)-DL-aspartateGenerator
UreidosuccinateGenerator
N-CarbamoylaspartateGenerator
N-Carbamoyl-D-aspartic acidMeSH
N-Carbamoyl-L-aspartic acidMeSH
N-Carbamoylaspartic acidMeSH
Carbamyl-DL-aspartateMeSH
Ureidosuccinic acid, (D)-isomerMeSH
Ureidosuccinic acid, (L)-isomerMeSH
Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomerMeSH
Ureidosuccinic acid, maganeese (+2), (1:1) saltMeSH
Ureidosuccinic acid, zinc (1:1) salt, (L)-isomerMeSH
Chemical FormulaC5H8N2O5
Average Mass176.1280 Da
Monoisotopic Mass176.04332 Da
IUPAC Name2-(carbamoylamino)butanedioic acid
Traditional Nameureidosuccinic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC(NC(O)=N)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)
InChI KeyHLKXYZVTANABHZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-1.7ChemAxon
logS-1.7ALOGPS
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
Polarizability14.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0159928  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbamoyl_aspartic_acid  
METLIN IDNot Available
PubChem Compound279  
PDB IDNot Available
ChEBI ID64850  
Good Scents IDNot Available
References
General References
  1. Golovinsky EV, Maneva LS, Angelov II, Veljanova KD, Sniker DJ, Stankevich EK: Antibacterial and antitumor activity of some derivatives of ureidosuccinic acid. Neoplasma. 1976;23(1):43-6. [PubMed:131912  ] 
  2. Greth ML, Chevallier MR, Lacroute F: Ureidosuccinic acid permeation in Saccharomyces cerevisiae. Biochim Biophys Acta. 1977 Feb 14;465(1):138-51. doi: 10.1016/0005-2736(77)90362-5. [PubMed:13831  ] 
  3. CROKAERT R: [Carbamoyl derivatives of amino acids of biological importance. II. N-Carbamoylaspartic acid. Separation technics and determination in urine in rat and man]. Bull Soc Chim Biol (Paris). 1961;43:1331-8. [PubMed:13882306  ] 
  4. ANDERSON EP, YEN CY, MANDEL HG, SMITH PK: Ureidosuccinic acid as a precursor of nucleic acid pyrimidines in normal and tumor-bearing mice. J Biol Chem. 1955 Apr;213(2):625-33. [PubMed:14367323  ] 
  5. SPICER DS, LIEBERT KV, WRIGHT LD, HUFF JW: Study of ureidosuccinic acid and related compounds in pyrimidine synthesis by Lactobacillus bulgaricus 09. Proc Soc Exp Biol Med. 1952 Apr;79(4):587-8. doi: 10.3181/00379727-79-19455. [PubMed:14920504  ] 
  6. LOTUS database [Link]