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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB001689 |
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Identification |
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| Name: |
Selenodiglutathione |
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| Description: | Selenodiglutathione is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Selenium compounds like selenite (SeO3(2-) may form a covalent adduct with glutathione (GSH) in the form of selenodiglutathione (GS-Se-SG), which is assumed to be important in the metabolism of selenium. GS-Se-SG to be a very efficient oxidant of reduced thioredoxin from Pseudomonas aeruginosa [PMID:1569062] |
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Structure |
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| Synonyms: | |
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Chemical Formula: |
C20H32N6O12S2Se |
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| Average Molecular Weight: |
691.59 |
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| Monoisotopic Molecular
Weight: |
692.068483726 |
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| InChI Key: |
GJEZZQVPWMCGSB-BJDJZHNGSA-N |
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| InChI: | InChI=1S/C20H32N6O12S2Se/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-41-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 |
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| CAS
number: |
33944-90-0 |
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| IUPAC Name: | (2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid |
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Traditional IUPAC Name: |
(2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}selanyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid |
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| SMILES: | N[C@@H](CCC(=O)N[C@@H](CS[Se]SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. |
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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 |
Peptides |
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| Alternative Parents |
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| Substituents |
- Alpha peptide
- N-acyl-aliphatic-alpha amino acid
- Tetracarboxylic acid or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- L-alpha-amino acid
- D-alpha-amino acid
- Alpha-amino acid or derivatives
- Alpha-amino acid
- Amino fatty acid
- Fatty acyl
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Sulfenyl compound
- Carboxylic acid
- Carboximidic acid derivative
- Carboximidic acid
- Hydrocarbon derivative
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- 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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| Charge: | -1 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Cytoplasm |
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| Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Bjornstedt, M., Kumar, S., Holmgren, A. (1992). "Selenodiglutathione is a highly efficient oxidant of reduced thioredoxin and a substrate for mammalian thioredoxin reductase." J Biol Chem 267:8030-8034. Pubmed: 1569062
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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