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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB001159 |
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Identification |
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| Name: |
Decarboxy-SAM |
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| Description: | dcSAM is a member of the chemical class known as Purine Nucleosides and Analogues. These are compounds comprising a purine base attached to a sugar. [2-(Amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium+ ++, the amino-oxy analogue of decarboxylated S-adenosylmethionine, is a potent irreversible inhibitor of Pseudomonas aeruginosa S-adenosylmethionine decarboxylase [Khomutov, Zavalova, Syrku, Artamonova & Khomutov (1983) Bioorg. (PMID 1872800) |
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Structure |
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| Synonyms: | - (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt
- (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt
- 3-amino-propyl-S-adenosine
- 3-Amino-propyl-S-adenosine
- S-adenosylmethioninamine
- S-methyl-S-adenosyl homocysteamine
- Dadomet
- DcSAM
- Decarboxylated adomet
- Decarboxylated S-adenosylmethionine
- Decarboxylated sam
- S-Adenosyl-(5')-3-methylthiopropylamine
- S-Adenosyl-L-methioninamine
- S-Adenosylmethioninamine
- S-Methyl-S-adenosyl homocysteamine
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Chemical Formula: |
C14H24N6O3S |
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| Average Molecular Weight: |
356.444 |
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| Monoisotopic Molecular
Weight: |
356.163059354 |
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| InChI Key: |
ZUNBITIXDCPNSD-LSRJEVITSA-O |
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| InChI: | InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/p+1/t8-,10-,11-,14-,24?/m1/s1 |
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| CAS
number: |
Not Available |
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| IUPAC Name: | {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-azaniumylpropyl)methylsulfanium |
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Traditional IUPAC Name: |
S-adenosylmethioninaminium |
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| SMILES: | [H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether). |
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Kingdom |
Organic compounds |
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| Super Class | Organooxygen compounds |
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Class |
Carbohydrates and carbohydrate conjugates |
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| Sub Class | Glycosyl compounds |
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Direct Parent |
Glycosylamines |
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| Alternative Parents |
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| Substituents |
- N-glycosyl compound
- 6-aminopurine
- Purine
- Imidazopyrimidine
- Aminopyrimidine
- Imidolactam
- Pyrimidine
- Primary aromatic amine
- N-substituted imidazole
- Monosaccharide
- Heteroaromatic compound
- Quaternary ammonium salt
- Oxolane
- Imidazole
- Azole
- Secondary alcohol
- 1,2-diol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Primary amine
- Organosulfur compound
- Organonitrogen compound
- Amine
- Alcohol
- 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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| Charge: | 2 |
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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: |
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Weitkamp, E. L., Dixon, H. B., Khomutov, A. R., Khomutov, R. M. (1991). "Effect of magnesium ions on the inhibition of S-adenosylmethionine decarboxylase from Escherichia coli by [2-(amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium ." Biochem J 277 ( Pt 3):643-645. Pubmed: 1872800
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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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