Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:07 UTC |
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Updated at | 2022-03-10 22:22:29 UTC |
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NP-MRD ID | NP0044293 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Selenohomocysteine |
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Description | Selenohomocysteine 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. Selenohomocysteine is a very strong basic compound (based on its pKa). Within humans, selenohomocysteine participates in a number of enzymatic reactions. In particular, L-serine and selenohomocysteine can be converted into selenocystathionine; which is catalyzed by the enzyme cystathionine beta-synthase. In addition, selenohomocysteine and adenosine can be biosynthesized from se-adenosylselenohomocysteine; which is mediated by the enzyme adenosylhomocysteinase. In humans, selenohomocysteine is involved in selenoamino acid metabolism. A selenoamino acid that is the selenium analogue of L-homocysteine. Selenohomocysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1 |
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Synonyms | Value | Source |
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Seleno-L-homocysteine | ChEBI | (2S)-2-Amino-4-selanylbutanoic acid | HMDB | (2S)-2-Amino-4-selenylbutanoic acid | HMDB | 2-Amino-4-selenobutanoic acid | HMDB | L-Selenohomocysteine | HMDB | Selenohomocysteine | ChEBI |
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Chemical Formula | C4H9NO2Se |
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Average Mass | 182.0920 Da |
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Monoisotopic Mass | 182.97985 Da |
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IUPAC Name | (2S)-2-amino-4-selanylbutanoic acid |
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Traditional Name | (2S)-2-amino-4-selanylbutanoic acid |
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CAS Registry Number | 29475-60-3 |
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SMILES | N[C@@H](CC[SeH])C(O)=O |
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InChI Identifier | InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1 |
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InChI Key | RCWCGLALNCIQNM-VKHMYHEASA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 | |
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Substituents | - L-alpha-amino acid
- Fatty acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Selenol
- Primary amine
- Organoselenium compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Soda K, Oikawa T, Esaki N: Vitamin B6 enzymes participating in selenium amino acid metabolism. Biofactors. 1999;10(2-3):257-62. doi: 10.1002/biof.5520100225. [PubMed:10609891 ]
- Liu G, Nellaiappan K, Kagan HM: Irreversible inhibition of lysyl oxidase by homocysteine thiolactone and its selenium and oxygen analogues. Implications for homocystinuria. J Biol Chem. 1997 Dec 19;272(51):32370-7. doi: 10.1074/jbc.272.51.32370. [PubMed:9405445 ]
- Esaki N, Nakamura T, Tanaka H, Suzuki T, Morino Y, Soda K: Enzymatic synthesis of selenocysteine in rat liver. Biochemistry. 1981 Jul 21;20(15):4492-6. doi: 10.1021/bi00518a039. [PubMed:6456763 ]
- Esaki N, Seraneeprakarn V, Tanaka H, Soda K: Purification and characterization of Clostridium sticklandii D-selenocystine alpha, beta-lyase. J Bacteriol. 1988 Feb;170(2):751-6. doi: 10.1128/jb.170.2.751-756.1988. [PubMed:3338973 ]
- Zhou ZS, Smith AE, Matthews RG: L-Selenohomocysteine: one-step synthesis from L-selenomethionine and kinetic analysis as substrate for methionine synthases. Bioorg Med Chem Lett. 2000 Nov 6;10(21):2471-5. doi: 10.1016/s0960-894x(00)00498-4. [PubMed:11078203 ]
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