Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:40:13 UTC |
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Updated at | 2022-03-10 22:22:18 UTC |
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NP-MRD ID | NP0044260 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | S-Adenosylmethionine |
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Description | S-Adenosylmethionine, also known as SAM or adomet, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-Adenosylmethionine is a very strong basic compound (based on its pKa). S-Adenosylmethionine exists in all living species, ranging from bacteria to humans. Within humans, S-adenosylmethionine participates in a number of enzymatic reactions. In particular, S-adenosylmethionine and glycine can be converted into S-adenosylhomocysteine and sarcosine; which is catalyzed by the enzyme dna (cytosine-5)-methyltransferase 1. In addition, S-adenosylmethionine can be converted into S-adenosylmethioninamine; which is catalyzed by the enzyme S-adenosylmethionine decarboxylase proenzyme. In humans, S-adenosylmethionine is involved in the metabolic disorder called the glycine n-methyltransferase deficiency pathway. Outside of the human body, S-Adenosylmethionine has been detected, but not quantified in, several different foods, such as malabar plums, sunflowers, purple mangosteens, cherry tomato, and pigeon pea. This could make S-adenosylmethionine a potential biomarker for the consumption of these foods. S-Adenosylmethionine is a potentially toxic compound. A sulfonium compound that is the S-adenosyl derivative of L-methionine. S-Adenosylmethionine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1 |
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Synonyms | Value | Source |
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(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt | ChEBI | [1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium | ChEBI | Acylcarnitine | ChEBI | AdoMet | ChEBI | S-(5'-Deoxyadenosin-5'-yl)-L-methionine | ChEBI | SAM | ChEBI | SAMe | ChEBI | (3S)-5'-[(3-Amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine, inner salt | Generator | [1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium | Generator | [1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium | Generator | [1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium | Generator | [1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium | Generator | [1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium | Generator | (3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine | HMDB | 2-S-Adenosyl-L-methionine | HMDB | 5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate | HMDB | 5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate | HMDB | Active methionine | HMDB | Ademetionine | HMDB | Adenosylmethionine | HMDB | Donamet | HMDB | L-S-Adenosylmethionine | HMDB | S-(5'-Adenosyl)-L-methionine | HMDB | S-Adenosyl methionine | HMDB | S-Adenosyl-L-methionine | HMDB | S-Adenosyl-L-methionine disulfate tosylate | HMDB | S-Adenosyl-L-methionine disulphate tosylate | HMDB | S-Adenosyl-methionine | HMDB | ASTA medica brand OF ademetionine tosilate disulfate | HMDB | S Adenosylmethionine sulfate tosylate | HMDB | S-Adenosylmethionine sulfate tosylate | HMDB | Sulfate tosylate, S-adenosylmethionine | HMDB | Ademetionine europharma brand | HMDB | Amet, S | HMDB | Europharma brand OF ademetionine | HMDB | Gumbaral | HMDB | Knoll brand OF brand OF ademetionine tosilate disulfate | HMDB | S Adenosylmethionine | HMDB | S Amet | HMDB | Samyr | HMDB | Tosylate, S-adenosylmethionine sulfate | HMDB | S Adenosyl L methionine | HMDB | SAM-e | HMDB |
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Chemical Formula | C15H23N6O5S |
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Average Mass | 399.4450 Da |
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Monoisotopic Mass | 399.14506 Da |
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IUPAC Name | [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium |
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Traditional Name | SAMe |
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CAS Registry Number | 485-80-3 |
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SMILES | C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N |
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InChI Identifier | InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1 |
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InChI Key | MEFKEPWMEQBLKI-AIRLBKTGSA-O |
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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 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | 5'-deoxyribonucleosides |
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Sub Class | 5'-deoxy-5'-thionucleosides |
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Direct Parent | 5'-deoxy-5'-thionucleosides |
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Alternative Parents | |
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Substituents | - 5'-deoxy-5'-thionucleoside
- Methionine or derivatives
- N-glycosyl compound
- Glycosyl compound
- Pentose monosaccharide
- 6-aminopurine
- Alpha-amino acid
- L-alpha-amino acid
- Alpha-amino acid or derivatives
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Hydroxy fatty acid
- Thia fatty acid
- N-substituted imidazole
- Fatty acyl
- Monosaccharide
- Imidolactam
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Tetrahydrofuran
- Amino acid or derivatives
- 1,2-diol
- Amino acid
- Secondary alcohol
- Oxacycle
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic oxide
- Organopnictogen compound
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Primary aliphatic amine
- Amine
- Organonitrogen compound
- Organic cation
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Koeberl DD, Young SP, Gregersen NS, Vockley J, Smith WE, Benjamin DK Jr, An Y, Weavil SD, Chaing SH, Bali D, McDonald MT, Kishnani PS, Chen YT, Millington DS: Rare disorders of metabolism with elevated butyryl- and isobutyryl-carnitine detected by tandem mass spectrometry newborn screening. Pediatr Res. 2003 Aug;54(2):219-23. Epub 2003 May 7. [PubMed:12736383 ]
- Struys EA, Jansen EE, de Meer K, Jakobs C: Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry. Clin Chem. 2000 Oct;46(10):1650-6. [PubMed:11017945 ]
- Chamberlin ME, Ubagai T, Mudd SH, Wilson WG, Leonard JV, Chou JY: Demyelination of the brain is associated with methionine adenosyltransferase I/III deficiency. J Clin Invest. 1996 Aug 15;98(4):1021-7. doi: 10.1172/JCI118862. [PubMed:8770875 ]
- Scalabrino G, Pigatto P, Ferioli ME, Modena D, Puerari M, Caru A: Levels of activity of the polyamine biosynthetic decarboxylases as indicators of degree of malignancy of human cutaneous epitheliomas. J Invest Dermatol. 1980 Mar;74(3):122-4. doi: 10.1111/1523-1747.ep12535012. [PubMed:7359002 ]
- Kaneoka H, Uesugi N, Moriguchi A, Hirose S, Takayanagi M, Yamaguchi S, Shigematsu Y, Yasuno T, Sasatomi Y, Saito T: Carnitine palmitoyltransferase II deficiency due to a novel gene variant in a patient with rhabdomyolysis and ARF. Am J Kidney Dis. 2005 Mar;45(3):596-602. doi: 10.1053/j.ajkd.2004.12.006. [PubMed:15754283 ]
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