2-Acetamido-3-hydroxypropanoic acid
PubChem CID: 352294
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| Compound Synonyms | 2-acetamido-3-hydroxypropanoic acid, 97-14-3, N-Acetyl-DL-serine, 2-Acetylamino-3-hydroxypropanoic acid, DL-Serine, N-acetyl-, 2-Acetylamino-3-hydroxy-propionic acid, N-Acetylserine #, MFCD00037248, N-Acetyl-D,L-serine, Serine, N-acetyl-, L-, SCHEMBL79541, CERAPP_36229, DTXSID60326233, DTXSID70864671, CHEBI:170015, 2-acetamido-3-hydroxypropanoicacid, NSC525646, 2-acetamido-3-oxidanyl-propanoic acid, AKOS000129548, FS-5616, HY-W142092, NSC-525646, DB-020341, CS-0201876, NS00014885, EN300-316982, F11099, A845685, Z239132792, 676EABE8-2F90-470B-A595-03DB023DE676 |
|---|---|
| Topological Polar Surface Area | 86.6 |
| Hydrogen Bond Donor Count | 3.0 |
| Inchi Key | JJIHLJJYMXLCOY-UHFFFAOYSA-N |
| Rotatable Bond Count | 3.0 |
| State | Solid |
| Substituent Name | N-acyl-aliphatic-alpha amino acid, Beta-hydroxy acid, Hydroxy acid, Organic 1,3-dipolar compound, Propargyl-type 1,3-dipolar organic compound, Monocarboxylic acid or derivatives, Carboxylic acid, Carboximidic acid derivative, Carboximidic acid, Hydrocarbon derivative, Primary alcohol, Organooxygen compound, Organonitrogen compound, Carbonyl group, Alcohol, Aliphatic acyclic compound |
| Synonyms | Acetylserine, L-serine, n-acetyl-, N-Acetyl-L-serine, N-acetylserine, Serine, n-acetyl-, l- |
| Heavy Atom Count | 10.0 |
| Compound Name | 2-Acetamido-3-hydroxypropanoic acid |
| Kingdom | Organic compounds |
| Description | Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians,80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians, 80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. N-acetylated proteins are catabolized in the cytosol by the ATP-ubiquitin-dependent proteasomal pathway. Several types of aminoacylases can be distinguished on the basis of substrate specificity. Aminoacylase I (ACY1, EC 3.5.1.14), the most abundant type, is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. It is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that comprises 15 exons (OMIM 609924). Preferred substrates of ACY1 are aliphatic amino acids with a short-chain acyl moiety, especially N-acetyl-methionine. However, ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Functional aminoacylase I is crucial in the last step in this degradation as it catalyzes the hydrolysis of N-acetylated amino acids into acetate and the free amino acid. Although N-acetylation occurs in many metabolic pathways and N-acetylated metabolites are known to accumulate in several inborn errors, there are only a few reports on N-acetylated amino acids detected in urine. Identification of N-acetylated amino acids by routine GC-MS may be problematic for several reasons. The major problem is linked to the identification strategy itself. Identification of an unknown compound in mass spectrometry is usually based on comparison of its spectrum against a library of reference spectra. (PMID: 16465618, 16274666, 17723438). N-Acetyl-L-serine is found in watermelon. |
| Exact Mass | 147.053 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 147.053 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 145.0 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 147.13 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Enzyme Uniprot Id | Q6IB77, Q969I3, Q8WU03 |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 2-acetamido-3-hydroxypropanoic acid |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Class | Carboxylic acids and derivatives |
| Inchi | InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10) |
| Smiles | CC(=O)NC(CO)C(=O)O |
| Xlogp | -1.2 |
| Superclass | Organic acids and derivatives |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Amino acids, peptides, and analogues |
| Molecular Formula | C5H9NO4 |
- 1. Outgoing r'ship
FOUND_INto/from Citrullus Lanatus (Plant) Rel Props:Source_db:fooddb_chem_all