Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:55:54 UTC |
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Updated at | 2020-11-18 16:39:08 UTC |
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CannabisDB ID | CDB004971 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | S-Hydroxymethylglutathione |
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Description | S-(Hydroxymethyl)glutathione, also known as sergsh, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. S-(Hydroxymethyl)glutathione is a very strong basic compound (based on its pKa). An S-substituted glutathione that is glutathione in which the mercapto hydrogen has been replaced by a hydroxymethyl group. S-(Hydroxymethyl)glutathione exists in all living species, ranging from bacteria to humans. S-Hydroxymethylglutathione is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACID | ChEBI, HMDB | S-Hydroxymethylglutathione | ChEBI | 2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrate | Generator, HMDB | 2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrate | Generator, HMDB | 2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acid | Generator, HMDB | S-Hydroxymethyl-glutathione | HMDB | SerGSH | MeSH, HMDB | Formaldehyde-glutathione thiohemiacetal | HMDB | Glutathione-formaldehyde thiohemiacetal | HMDB | L-gamma-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine | HMDB | L-γ-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine | HMDB | S-(Hydroxymethyl)glutathione | HMDB |
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Chemical Formula | C11H19N3O7S |
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Average Molecular Weight | 337.35 |
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Monoisotopic Molecular Weight | 337.0944 |
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IUPAC Name | (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid |
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Traditional Name | S-hydroxymethylglutathione |
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CAS Registry Number | 32260-87-0 |
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SMILES | N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 |
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InChI Key | PIUSLWSYOYFRFR-BQBZGAKWSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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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 | Oligopeptides |
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Alternative Parents | |
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Substituents | - Alpha-oligopeptide
- Gamma-glutamyl alpha peptide
- Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Cysteine or derivatives
- Alpha-amino acid
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Fatty amide
- Fatty acyl
- Fatty acid
- N-acyl-amine
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Secondary carboxylic acid amide
- Sulfenyl compound
- Carboxylic acid
- Organopnictogen compound
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Amine
- Organic oxide
- Primary amine
- Organosulfur compound
- Organonitrogen compound
- Organooxygen compound
- 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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Disposition | Biological location: Source: |
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Role | Industrial application: |
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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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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | S-Hydroxymethylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01po-6291000000-700a78b68cd3c72dace0 | Spectrum | Predicted GC-MS | S-Hydroxymethylglutathione, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ukl-9410370000-758e7d3d20ef5e803fa9 | Spectrum | Predicted GC-MS | S-Hydroxymethylglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00du-0195000000-0fb852c5aa71ebfacbc3 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0570-4690000000-74c4fbcadf9e75cea5e6 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-4920000000-a75d217a2989134725ab | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052r-5089000000-0963b985ed393a77403b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05di-5393000000-80626db3d68b3e84d33f | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03fu-9200000000-c770bc62700bd5b4872c | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0029000000-9285be543171793a7f61 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6u-1941000000-3b0ed9e0505deb83df54 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9400000000-cdcded7632edf6274abf | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05g0-0193000000-b9ae6fff6991f7a74ac1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03e9-9440000000-4e976999daadff083f1c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dl-9400000000-49e525bdebda32941d94 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | HMDB0004662 |
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DrugBank ID | DB04153 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023393 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 394301 |
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KEGG Compound ID | C14180 |
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BioCyc ID | S-HYDROXYMETHYLGLUTATHIONE |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 7068 |
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PubChem Compound | 447123 |
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PDB ID | AHE |
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ChEBI ID | 48926 |
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References |
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General References | Not Available |
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