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Basic information
- CAS
485-80-3- Standard SMILES
C[S+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O- InChIKey
MEFKEPWMEQBLKI-AIRLBKTGSA-O- Molecular formula
- C15H23N6O5S+
- Average molar mass
- 399.4 g/mol
- Monoisotopic mass
- 399.14451526
Overview
S-adenosyl-L-methionine is a sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine. It has a role as a Mycoplasma genitalium metabolite, a coenzyme, a cofactor, a micronutrient, a nutraceutical, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a conjugate acid of a S-adenosyl-L-methioninate. It is an enantiomer of a S-adenosyl-D-methionine. It is a tautomer of a S-adenosyl-L-methionine zwitterion.
Names & identifiers
- Preferred name
- S-adenosyl-L-methionine
- IUPAC
- [(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium
Names & synonyms
S-adenosyl-L-methionine485-80-3SAMeadenosylmethionineCHEMBL224120Methionine, S-adenosyl-S-(5'-Adenosyl)-L-methionineCHEBI:15414(R)-S-adenosyl-L-methionine(S)-S-adenosyl-L-methionine((S)-3-Amino-3-carboxypropyl)(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)sulfoniumS-(5'-deoxyadenosin-5'-yl)-L-methionine
Show more names
(R,S)-AdoMet(S,S)-AdoMet2-S-adenosyl-L-methionineSAMNCGC00167546-02ademethionineAdoMeAdenosine, 5'-[[(3S)-3-amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-
Database identifiers
- CAS
485-80-3- PubChem CID
- 34756
- DTXSID
DTXSID20110014- ChEMBL
CHEMBL224120- ChEBI
CHEBI:15414- Nikkaji
- J260.469H
Properties
Computed structural propertiesFilling in
- XLogP
- -3.5
- Topological polar surface area
- 184 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 1
- Complexity
- 533
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP-5.3
Boiling Point78 °C
Physical DescriptionSolid
Collision Cross Section185.6 Ų [M+H]+
Safety & regulation
Toxicology
Exposure RoutesS-Adenosylmethionine is absorbed from the small intestine following oral intake. As absorption is affected by food, it is best to take on an empty stomach. Bioavailability is low following oral intake.
Toxicity Summary
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
ATC CodeQA - Alimentary tract and metabolism
Metabolism/Metabolites
Significant first-pass metabolism in the liver. Approximately 50% of S-Adenosylmethionine (SAMe) is metabolized in the liver. SAMe is metabolized to S-adenosylhomocysteine, which is then metabolized to homocysteine. Homocysteine can either be metabolized to cystathionine and then cysteine or to methionine. The cofactor in the metabolism of homocysteine to cysteine is vitamin B6. Cofactors for the metabolism of homocysteine to methionine are folic acid, vitamin B12 and betaine.
Tissue LocationsEpidermis
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
Uses
S-Adenosylmethionine (SAMe) is used as a drug in Europe for the treatment of depression, liver disorders, fibromyalgia, and osteoarthritis. It has also been introduced into the United States market as a dietary supplement for the support of bone and joint health, as well as mood and emotional well being.
Related reactions
3 records
Compound notes
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