Showing Metabocard for N-carbamoyl-L-aspartate (BASm0001855)
| Common Name | N-carbamoyl-l-aspartate | ||||||||||||||||||
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| Description | Ureidosuccinic 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 | |||||||||||||||||||
| Molecular Formula | C5H8N2O5 | ||||||||||||||||||
| Average Mass | 176.12740 | ||||||||||||||||||
| Monoisotopic Mass | 176.04332 | ||||||||||||||||||
| IUPAC Name | (2S)-2-(carbamoylamino)butanedioic acid | ||||||||||||||||||
| Traditional Name | N-carbamoyl-l-aspartate | ||||||||||||||||||
| 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 | ||||||||||||||||||
| CHEBI ID | CHEBI:32814 | ||||||||||||||||||
| HMDB ID | HMDB0000828 | ||||||||||||||||||
| Pathways |
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| State | Not Available | ||||||||||||||||||
| Water Solubility | 2.13e+01 g/l | ||||||||||||||||||
| logP | -1.12 | ||||||||||||||||||
| logS | -0.92 | ||||||||||||||||||
| pKa (Strongest Acidic) | 3.33 | ||||||||||||||||||
| pKa (Strongest Basic) | -2.59 | ||||||||||||||||||
| Hydrogen Acceptor Count | 5 | ||||||||||||||||||
| Hydrogen Donor Count | 4 | ||||||||||||||||||
| Polar Surface Area | 129.72 Ų | ||||||||||||||||||
| Rotatable Bond Count | 4 | ||||||||||||||||||
| Physiological Charge | -2 | ||||||||||||||||||
| Formal Charge | 0 | ||||||||||||||||||
| Refractivity | 34.65 m³·mol⁻¹ | ||||||||||||||||||
| Polarizability | 14.62 |