Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:38:41 UTC |
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Updated at | 2021-08-19 23:59:17 UTC |
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NP-MRD ID | NP0002718 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | L-Cysteic acid |
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Provided By | BMRB |
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Description | (R)-cysteate, also known as L-cysteic acid or 3-sulfoalanine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom (R)-cysteate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. L-Cysteic acid is found in Apis cerana, Claviceps purpurea, Pseudotsuga menziesii and Puccinia graminis. It was first documented in 1996 (PMID: 8981569). Based on a literature review a significant number of articles have been published on (R)-cysteate (PMID: 17984079) (PMID: 11750815) (PMID: 21719707) (PMID: 34364050) (PMID: 34269883) (PMID: 34268896). |
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Structure | N[C@@H](CS(O)(=O)=O)C(O)=O InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1 |
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Synonyms | Value | Source |
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(2R)-2-Amino-3-sulfopropanoic acid | ChEBI | 2-Amino-3-sulfopropionic acid | ChEBI | 3-SulfO-L-alanine | ChEBI | 3-Sulfoalanine | ChEBI | CYSTEINEsulfonIC ACID | ChEBI | L-Cysteate | ChEBI | L-Cysteic acid | Kegg | (2R)-2-Amino-3-sulfopropanoate | Generator | (2R)-2-Amino-3-sulphopropanoate | Generator | (2R)-2-Amino-3-sulphopropanoic acid | Generator | 2-Amino-3-sulfopropionate | Generator | 2-Amino-3-sulphopropionate | Generator | 2-Amino-3-sulphopropionic acid | Generator | 3-SulphO-L-alanine | Generator | 3-Sulphoalanine | Generator | CYSTEINEsulfonate | Generator | CYSTEINEsulphonate | Generator | CYSTEINEsulphonic acid | Generator | (R)-Cysteic acid | Generator | L-3-Sulfoalanine | HMDB | Cysteic acid | HMDB | 2-Amino-3-sulfopropanoic acid | HMDB | Cysteate | HMDB | DL-Cysteic acid | HMDB |
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Chemical Formula | C3H7NO5S |
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Average Mass | 169.1560 Da |
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Monoisotopic Mass | 169.00449 Da |
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IUPAC Name | (2R)-2-amino-3-sulfopropanoic acid |
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Traditional Name | cysteinesulfonic acid |
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CAS Registry Number | Not Available |
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SMILES | N[C@@H](CS(O)(=O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1 |
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InChI Key | XVOYSCVBGLVSOL-REOHCLBHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as l-alpha-amino acids. These are 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 | L-alpha-amino acids |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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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 | 1000000 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Eichhorn E, Leisinger T: Escherichia coli utilizes methanesulfonate and L-cysteate as sole sulfur sources for growth. FEMS Microbiol Lett. 2001 Dec 18;205(2):271-5. doi: 10.1111/j.1574-6968.2001.tb10960.x. [PubMed:11750815 ]
- Sasahara A, Nanatani K, Enomoto M, Kuwahara S, Abe K: Substrate specificity of the aspartate:alanine antiporter (AspT) of Tetragenococcus halophilus in reconstituted liposomes. J Biol Chem. 2011 Aug 19;286(33):29044-29052. doi: 10.1074/jbc.M111.260224. Epub 2011 Jun 30. [PubMed:21719707 ]
- Thompson GA, Kilpatrick IC: The neurotransmitter candidature of sulphur-containing excitatory amino acids in the mammalian central nervous system. Pharmacol Ther. 1996;72(1):25-36. doi: 10.1016/s0163-7258(96)00097-6. [PubMed:8981569 ]
- Gorican T, Ciber L, Petek N, Svete J, Novinec M: Synthesis and kinetic characterization of hyperbolic inhibitors of human cathepsins K and S based on a succinimide scaffold. Bioorg Chem. 2021 Jul 28;115:105213. doi: 10.1016/j.bioorg.2021.105213. [PubMed:34364050 ]
- Schwenk ES, Pradhan B, Nalamasu R, Stolle L, Wainer IW, Cirullo M, Olsen A, Pergolizzi JV, Torjman MC, Viscusi ER: Ketamine in the Past, Present, and Future: Mechanisms, Metabolites, and Toxicity. Curr Pain Headache Rep. 2021 Jul 16;25(9):57. doi: 10.1007/s11916-021-00977-w. [PubMed:34269883 ]
- Han ZZ, Dong T, Ming XX, Kuang F, Zhang CP: Synthesis and Biological Evaluation of CF3 Se-Substituted alpha-Amino Acid Derivatives. ChemMedChem. 2021 Jul 15. doi: 10.1002/cmdc.202100451. [PubMed:34268896 ]
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