Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:20 UTC |
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Update Date | 2023-05-30 20:56:00 UTC |
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HMDB ID | HMDB0002931 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Acetylserine |
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Description | N-Acetyl-L-serine or N-Acetylserine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylserine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylserine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-serine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylserine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free serine can also occur. Excessive amounts N-acetyl amino acids including N-acetylserine (as well as N-acetylglycine, N-acetylglutamine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylserine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). |
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Structure | InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1 |
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Synonyms | Value | Source |
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Acetylserine | HMDB | N-Acetyl-L-serine | HMDB | (2S)-2-Acetamido-3-hydroxypropanoic acid | HMDB | (2S)-2-Acetamido-3-hydroxypropionic acid | HMDB | (S)-2-Acetamido-3-hydroxypropanoic acid | HMDB | (S)-2-Acetamido-3-hydroxypropionic acid | HMDB | N-Acetylserine | MeSH |
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Chemical Formula | C5H9NO4 |
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Average Molecular Weight | 147.1293 |
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Monoisotopic Molecular Weight | 147.053157781 |
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IUPAC Name | (2S)-2-acetamido-3-hydroxypropanoic acid |
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Traditional Name | acetylserine |
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CAS Registry Number | 16354-58-8 |
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SMILES | CC(=O)N[C@@H](CO)C(O)=O |
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InChI Identifier | InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1 |
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InChI Key | JJIHLJJYMXLCOY-BYPYZUCNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-l-alpha-amino acid
- Serine or derivatives
- Beta-hydroxy acid
- Hydroxy acid
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 207.6 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Acetylserine,1TMS,isomer #1 | CC(=O)N[C@@H](CO[Si](C)(C)C)C(=O)O | 1391.3 | Semi standard non polar | 33892256 | N-Acetylserine,1TMS,isomer #2 | CC(=O)N[C@@H](CO)C(=O)O[Si](C)(C)C | 1415.4 | Semi standard non polar | 33892256 | N-Acetylserine,1TMS,isomer #3 | CC(=O)N([C@@H](CO)C(=O)O)[Si](C)(C)C | 1436.9 | Semi standard non polar | 33892256 | N-Acetylserine,2TMS,isomer #1 | CC(=O)N[C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1479.7 | Semi standard non polar | 33892256 | N-Acetylserine,2TMS,isomer #2 | CC(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1506.9 | Semi standard non polar | 33892256 | N-Acetylserine,2TMS,isomer #3 | CC(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1437.0 | Semi standard non polar | 33892256 | N-Acetylserine,3TMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1539.0 | Semi standard non polar | 33892256 | N-Acetylserine,3TMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1558.9 | Standard non polar | 33892256 | N-Acetylserine,3TMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1643.3 | Standard polar | 33892256 | N-Acetylserine,1TBDMS,isomer #1 | CC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O | 1636.0 | Semi standard non polar | 33892256 | N-Acetylserine,1TBDMS,isomer #2 | CC(=O)N[C@@H](CO)C(=O)O[Si](C)(C)C(C)(C)C | 1653.4 | Semi standard non polar | 33892256 | N-Acetylserine,1TBDMS,isomer #3 | CC(=O)N([C@@H](CO)C(=O)O)[Si](C)(C)C(C)(C)C | 1696.8 | Semi standard non polar | 33892256 | N-Acetylserine,2TBDMS,isomer #1 | CC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1909.6 | Semi standard non polar | 33892256 | N-Acetylserine,2TBDMS,isomer #2 | CC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 1958.5 | Semi standard non polar | 33892256 | N-Acetylserine,2TBDMS,isomer #3 | CC(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1923.2 | Semi standard non polar | 33892256 | N-Acetylserine,3TBDMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2190.2 | Semi standard non polar | 33892256 | N-Acetylserine,3TBDMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2202.8 | Standard non polar | 33892256 | N-Acetylserine,3TBDMS,isomer #1 | CC(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2089.7 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - N-Acetylserine GC-MS (2 TMS) | splash10-0v4r-1910000000-55bfa57992b993e5736a | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Acetylserine GC-MS (Non-derivatized) | splash10-0v4r-1910000000-55bfa57992b993e5736a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetylserine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9300000000-6b0aa9c8cd5d65af598e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetylserine GC-MS (2 TMS) - 70eV, Positive | splash10-00dl-9640000000-e19818dfd1f671358afc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetylserine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Acetylserine 20V, Negative-QTOF | splash10-00ec-9000000000-ea3c1cb050105f5513c0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Acetylserine 10V, Negative-QTOF | splash10-00ea-9300000000-ecc32dc021c318a085a1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Acetylserine 30V, Negative-QTOF | splash10-006x-9000000000-ec47f807a87862b61560 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Acetylserine 40V, Negative-QTOF | splash10-0006-9000000000-6b0d326c6e06fd4000da | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 10V, Positive-QTOF | splash10-001j-2900000000-cbbd7e861694a1b35ef0 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 20V, Positive-QTOF | splash10-0il9-9500000000-450a2fd0cc806534a001 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 40V, Positive-QTOF | splash10-001c-9000000000-92b250da801d4279b0ce | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 10V, Negative-QTOF | splash10-0f6t-2900000000-4a518dea349294701f1d | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 20V, Negative-QTOF | splash10-0ugs-9800000000-1fd980296f0d35c624aa | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 40V, Negative-QTOF | splash10-0a4l-9100000000-b2ff3e9d761c45d69c15 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 10V, Positive-QTOF | splash10-0bt9-7900000000-2b2025d17af2e7713b6d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 20V, Positive-QTOF | splash10-03dr-9200000000-168efcb7664c27577d54 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 40V, Positive-QTOF | splash10-03dl-9000000000-5f40a5d675fc08643864 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 10V, Negative-QTOF | splash10-00di-9300000000-9296333e726065a0a297 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 20V, Negative-QTOF | splash10-05fr-9100000000-04b2db5af6f8b258f271 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylserine 40V, Negative-QTOF | splash10-0006-9000000000-e1a13303be43e1757dfa | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 5.02 (2.63-8.14) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Urine | Detected and Quantified | 104 (99-111) umol/mmol creatinine | Adult (>18 years old) | Not Specified | Aminoacylase I deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Aminoacylase I deficiency |
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- Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
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Associated OMIM IDs | - 609924 (Aminoacylase I deficiency)
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External Links |
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DrugBank ID | DB02340 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000970 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 58744 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | O-Acetylserine |
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METLIN ID | 308 |
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PubChem Compound | 65249 |
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PDB ID | Not Available |
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ChEBI ID | 45441 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Tsurumi, Kohti; Yamada, Sakae. L-Serine from D-glucosamine. Tohoku Journal of Experimental Medicine (1955), 62 329-31. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
- Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
- Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
- Boesgaard S, Aldershvile J, Poulsen HE, Christensen S, Dige-Petersen H, Giese J: N-acetylcysteine inhibits angiotensin converting enzyme in vivo. J Pharmacol Exp Ther. 1993 Jun;265(3):1239-44. [PubMed:8389858 ]
- Lynch AS, Tyrrell R, Smerdon SJ, Briggs GS, Wilkinson AJ: Characterization of the CysB protein of Klebsiella aerogenes: direct evidence that N-acetylserine rather than O-acetylserine serves as the inducer of the cysteine regulon. Biochem J. 1994 Apr 1;299 ( Pt 1):129-36. [PubMed:8166630 ]
- Gerlo E, Van Coster R, Lissens W, Winckelmans G, De Meirleir L, Wevers R: Gas chromatographic-mass spectrometric analysis of N-acetylated amino acids: the first case of aminoacylase I deficiency. Anal Chim Acta. 2006 Jul 7;571(2):191-9. Epub 2006 May 5. [PubMed:17723438 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
- Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
- Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
- Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
- Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
- Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]
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