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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:51 UTC |
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Update Date | 2020-02-26 21:24:07 UTC |
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HMDB ID | HMDB0002381 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Acetylcystathionine |
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Description | N-Acetylcystathionine, also known as nac-cysta, 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-Acetylcystathionine is a very strong basic compound (based on its pKa). N-Acetylcystathionine, with regard to humans, has been linked to the inborn metabolic disorder cystathioninuria. |
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Structure | |
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Synonyms | Value | Source |
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N-Monoacetylcystathionine | HMDB | Nac-cysta | HMDB | S-(2-(Acetylamino)-2-carboxyethyl)-L-homocysteine | HMDB | S-(L-2-(Acetylamino)-2-carboxyethyl)-L-homocysteine | HMDB | (2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)butanoate | HMDB | (2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)butanoate | HMDB | (2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)butanoic acid | HMDB |
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Chemical Formula | C9H16N2O5S |
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Average Molecular Weight | 264.299 |
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Monoisotopic Molecular Weight | 264.077992322 |
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IUPAC Name | (2S)-2-amino-4-[(2-carboxy-2-acetamidoethyl)sulfanyl]butanoic acid |
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Traditional Name | (2S)-2-amino-4-[(2-carboxy-2-acetamidoethyl)sulfanyl]butanoic acid |
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CAS Registry Number | 20619-80-1 |
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SMILES | CC(=O)NC(CSCC[C@H](N)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C9H16N2O5S/c1-5(12)11-7(9(15)16)4-17-3-2-6(10)8(13)14/h6-7H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t6-,7?/m0/s1 |
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InChI Key | QWACVTVBTRSCRL-PKPIPKONSA-N |
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Chemical Taxonomy |
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Description | 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. |
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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-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Cysteine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Thia fatty acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Fatty acyl
- Acetamide
- Amino acid
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Dialkylthioether
- Thioether
- Sulfenyl compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organic oxide
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-006x-9220000000-72ff365709580fd404f5 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-006x-9311000000-ad841d4cc92e0e5ed39b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0590000000-db0ea3d4b6872a696df6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05px-7930000000-14a2bb074489a863d8c0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f8i-8900000000-a064391c7ff453f93812 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1790000000-5e1a61a1973e6b217935 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3940000000-b45c7441294a69453464 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0540-9400000000-1c9a833247eb0f22dd70 | 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 | Not Available |
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Pathways | |
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Normal Concentrations |
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Urine | Detected and Quantified | <40 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 20.0 (8.8-31.0) umol/mmol creatinine | Children (1-13 years old) | Both | Gamma-Cystathionase deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Cystathioninuria |
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- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022987 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 134252 |
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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 | Not Available |
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METLIN ID | 6656 |
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PubChem Compound | 152314 |
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PDB ID | Not Available |
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ChEBI ID | 88610 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Watanabe H, Fujita Y, Sugahara K, Kodama H, Ohmori S: Identification of NAc-HCPC and NAc-beta-CEC, and qualitative analyses of sulphur amino acids in the urine of a patient with cystathioninuria using liquid chromatography/atmospheric pressure ionization mass spectrometry. Biol Mass Spectrom. 1991 Oct;20(10):602-8. [PubMed:1793738 ]
- Ito O, Zhang J, Zhang M, Sagara Y, Masuoka N, Ubuka T, Kodama H: Priming effect of N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine in human neutrophils and tyrosyl phosphorylation of 45 kDa protein. Clin Chim Acta. 1997 Oct 31;266(2):93-104. [PubMed:9437538 ]
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