S-Adenosylmethionine

Basic Info

Common NameS-Adenosylmethionine(F05383)
2D Structure
Description

Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed).
S-Adenosylmethionine is only found in individuals that have used or taken this drug. It is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.

FRCD IDF05383
CAS Number29908-03-0
PubChem CID34756
FormulaC15H23N6O5S+
IUPAC Name

[(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium

InChI Key

MEFKEPWMEQBLKI-AIRLBKTGSA-O

InChI

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

Canonical SMILES

C[S+](CCC(C(=O)O)N)CC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O

Isomeric SMILES

C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)O

WikipediaS-Adenosylmethionine
Synonyms
        
            S-adenosyl methionine
        
            S-adenosyl-L-methionine
        
            S-adenosylmethionine
        
            SAMe
        
            Donamet
        
            adenosylmethionine
        
            Active methionine
        
            29908-03-0
        
            S-(5'-Adenosyl)-L-methionine
        
            CHEBI:15414
Classifies
                

                  
                    Animal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Subclass5'-deoxy-5'-thionucleosides
Intermediate Tree NodesNot available
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents5'-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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight399.446
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Complexity533
Monoisotopic Mass399.145
Exact Mass399.145
XLogP-3.5
Formal Charge1
Heavy Atom Count27
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

References

TitleJournalDatePubmed ID
Impact of prenatal arsenic exposure on chronic adult diseases.Syst Biol Reprod Med2018 Jun 629873257
Nutritional management can assist a significant role in alleviation of arsenicosis.J Trace Elem Med Biol2018 Jan29173466
The <i>Aspergillus flavus</i> Spermidine Synthase (<i>spds</i>) Gene, Is Required for Normal Development, Aflatoxin Production, and Pathogenesis During Infection of Maize Kernels.Front Plant Sci201829616053
Acute and long-term administration of palmitoylcarnitine induces muscle-specific insulin resistance in mice.Biofactors2017 Sep 1028759135
Proteomics analysis of Fusarium proliferatum under various initial pH during fumonisin production.J Proteomics2017 Jul 528522339
Accumulation of Palmitoylcarnitine and Its Effect on Pro-Inflammatory Pathwaysand Calcium Influx in Prostate Cancer.Prostate2016 Oct27403764
DHA at nutritional doses restores insulin sensitivity in skeletal muscle bypreventing lipotoxicity and inflammation.J Nutr Biochem2015 Sep26007287
Hepatopathy following consumption of a commercially available blue-green algae dietary supplement in a dog.BMC Vet Res2015 Jun 1926087767
Trans-sulfuration Pathway Seleno-amino Acids Are Mediators of Selenomethionine Toxicity in Saccharomyces cerevisiae.J Biol Chem2015 Apr 2425745108
Crystallization and preliminary X-ray crystallographic studies of CrArsM, an arsenic(III) S-adenosylmethionine methyltransferase from Chlamydomonas reinhardtii.Acta Crystallogr F Struct Biol Commun2014 Oct25286945
Response of the hepatic transcriptome to aflatoxin B1 in domestic turkey (Meleagris gallopavo).PLoS One201424979717
Autism: metabolism, mitochondria, and the microbiome.Glob Adv Health Med2013 Nov24416709
Engineering the soil bacterium Pseudomonas putida for arsenic methylation.Appl Environ Microbiol2013 Jul23645194
Comparative proteomics and physiological characterization of Arabidopsis thaliana seedlings in responses to Ochratoxin A.Plant Mol Biol2013 Jul23625346
Bioavailability of S-adenosyl methionine and impact on response in a randomized, double-blind, placebo-controlled trial in major depressive disorder.J Clin Psychiatry2012 Jun22687580
Stevia rebaudiana Bertoni extract supplementation improves lipid and carnitineprofiles in C57BL/6J mice fed a high-fat diet.J Sci Food Agric2010 May20393989
Evidence for a lineage of virulent bacteriophages that target Campylobacter.BMC Genomics2010 Mar 3020353581
Evaluations of the trans-sulfuration pathway in multiple liver toxicity studies.Toxicol Appl Pharmacol2009 Feb 1519103213
Liposome dependent delivery of S-adenosyl methionine to cells by liposomes: a potential treatment for liver disease.J Pharm Sci2009 Feb18642386
Serum carnitine concentrations correlated to clinical outcome parameters inchronic hemodialysis patients.Clin Nutr2004 Feb14757390

Targets

Target Details

S-adenosylmethionine synthase isoform type-1

General Function:
Methionine adenosyltransferase activity
Specific Function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT1A
Uniprot ID:
Q00266
Molecular Weight:
43647.6 Da
References
  1. Martinez-Chantar ML, Latasa MU, Varela-Rey M, Lu SC, Garcia-Trevijano ER, Mato JM, Avila MA: L-methionine availability regulates expression of the methionine adenosyltransferase 2A gene in human hepatocarcinoma cells: role of S-adenosylmethionine. J Biol Chem. 2003 May 30;278(22):19885-90. Epub 2003 Mar 26. [12660248 ]
Target Details

S-adenosylmethionine decarboxylase proenzyme

General Function:
Putrescine binding
Specific Function:
Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
Gene Name:
AMD1
Uniprot ID:
P17707
Molecular Weight:
38339.335 Da
References
  1. Dudkowska M, Stachurska A, Grzelakowska-Sztabert B, Manteuffel-Cymborowska M: Up-regulation of spermidine/spermine N1-acetyltransferase (SSAT) expression is a part of proliferative but not anabolic response of mouse kidney. Acta Biochim Pol. 2002;49(4):969-77. [12545203 ]
Target Details

S-adenosylmethionine synthase isoform type-2

General Function:
Methionine adenosyltransferase activity
Specific Function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT2A
Uniprot ID:
P31153
Molecular Weight:
43660.37 Da
References
  1. Mudd SH, Cerone R, Schiaffino MC, Fantasia AR, Minniti G, Caruso U, Lorini R, Watkins D, Matiaszuk N, Rosenblatt DS, Schwahn B, Rozen R, LeGros L, Kotb M, Capdevila A, Luka Z, Finkelstein JD, Tangerman A, Stabler SP, Allen RH, Wagner C: Glycine N-methyltransferase deficiency: a novel inborn error causing persistent isolated hypermethioninaemia. J Inherit Metab Dis. 2001 Aug;24(4):448-64. [11596649 ]
Target Details

Catechol O-methyltransferase

General Function:
O-methyltransferase activity
Specific Function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular Weight:
30036.77 Da
References
  1. Lee BW, Sun HG, Zang T, Kim BJ, Alfaro JF, Zhou ZS: Enzyme-catalyzed transfer of a ketone group from an S-adenosylmethionine analogue: a tool for the functional analysis of methyltransferases. J Am Chem Soc. 2010 Mar 24;132(11):3642-3. doi: 10.1021/ja908995p. [20196537 ]
Target Details

Methionine synthase

General Function:
Zinc ion binding
Specific Function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular Weight:
140525.91 Da
References
  1. Wolthers KR, Scrutton NS: Protein interactions in the human methionine synthase-methionine synthase reductase complex and implications for the mechanism of enzyme reactivation. Biochemistry. 2007 Jun 12;46(23):6696-709. Epub 2007 May 4. [17477549 ]
Target Details

Phenylethanolamine N-methyltransferase

General Function:
Phenylethanolamine n-methyltransferase activity
Specific Function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular Weight:
30854.745 Da
References
  1. Wu Q, Gee CL, Lin F, Tyndall JD, Martin JL, Grunewald GL, McLeish MJ: Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase. J Med Chem. 2005 Nov 17;48(23):7243-52. [16279783 ]
Target Details

Protein-L-isoaspartate(D-aspartate) O-methyltransferase

General Function:
Protein-l-isoaspartate (d-aspartate) o-methyltransferase activity
Specific Function:
Catalyzes the methyl esterification of L-isoaspartyl and D-aspartyl residues in peptides and proteins that result from spontaneous decomposition of normal L-aspartyl and L-asparaginyl residues. It plays a role in the repair and/or degradation of damaged proteins. Acts on EIF4EBP2, microtubule-associated protein 2, calreticulin, clathrin light chains a and b, Ubiquitin carboxyl-terminal hydrolase isozyme L1, phosphatidylethanolamine-binding protein 1, stathmin, beta-synuclein and alpha-synuclein.
Gene Name:
PCMT1
Uniprot ID:
P22061
Molecular Weight:
24636.21 Da
References
  1. Barton DH, Gero SD, Lawrence F, Robert-Gero M, Quiclet-Sire B, Samadi M: Total synthesis of uracil analogues of sinefungin. J Med Chem. 1992 Jan;35(1):63-7. [1732534 ]
Target Details

Glycine N-methyltransferase

General Function:
Glycine n-methyltransferase activity
Specific Function:
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular Weight:
32742.0 Da
References
  1. Rowling MJ, Schalinske KL: Retinoid compounds activate and induce hepatic glycine N-methyltransferase in rats. J Nutr. 2001 Jul;131(7):1914-7. [11435507 ]
Target Details

Cystathionine beta-synthase

General Function:
Ubiquitin protein ligase binding
Specific Function:
Hydro-lyase catalyzing the first step of the transsulfuration pathway, where the hydroxyl group of L-serine is displaced by L-homocysteine in a beta-replacement reaction to form L-cystathionine, the precursor of L-cysteine. This catabolic route allows the elimination of L-methionine and the toxic metabolite L-homocysteine (PubMed:23981774, PubMed:20506325, PubMed:23974653). Also involved in the production of hydrogen sulfide, a gasotransmitter with signaling and cytoprotective effects on neurons (By similarity).
Gene Name:
CBS
Uniprot ID:
P35520
Molecular Weight:
60586.05 Da
References
  1. Janosik M, Kery V, Gaustadnes M, Maclean KN, Kraus JP: Regulation of human cystathionine beta-synthase by S-adenosyl-L-methionine: evidence for two catalytically active conformations involving an autoinhibitory domain in the C-terminal region. Biochemistry. 2001 Sep 4;40(35):10625-33. [11524006 ]
Target Details

Protein arginine N-methyltransferase 1

General Function:
Protein-arginine omega-n asymmetric methyltransferase activity
Specific Function:
Arginine methyltransferase that methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues present in proteins such as ESR1, histone H2, H3 and H4, PIAS1, HNRNPA1, HNRNPD, NFATC2IP, SUPT5H, TAF15 and EWS. Constitutes the main enzyme that mediates monomethylation and asymmetric dimethylation of histone H4 'Arg-4' (H4R3me1 and H4R3me2a, respectively), a specific tag for epigenetic transcriptional activation. Together with dimethylated PIAS1, represses STAT1 transcriptional activity, in the late phase of interferon gamma (IFN-gamma) signaling. May be involved in the regulation of TAF15 transcriptional activity, act as an activator of estrogen receptor (ER)-mediated transactivation, play a key role in neurite outgrowth and act as a negative regulator of megakaryocytic differentiation, by modulating p38 MAPK pathway. Methylates FOXO1 and retains it in the nucleus increasing its transcriptional activity.
Gene Name:
PRMT1
Uniprot ID:
Q99873
Molecular Weight:
41515.2 Da
References
  1. Dowden J, Hong W, Parry RV, Pike RA, Ward SG: Toward the development of potent and selective bisubstrate inhibitors of protein arginine methyltransferases. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2103-5. doi: 10.1016/j.bmcl.2010.02.069. Epub 2010 Feb 20. [20219369 ]