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S-adenosyl methionine   Click here for help

GtoPdb Ligand ID: 4786

Synonyms: AdoMet | S-adenosyl-L-methionine | S-adenosylmethionine | SAM-e | SAMe
Compound class: Metabolite
Comment: This compound is sold as a nutritional supplement in the US and Canada and is approved as a prescription drug in some EU countries (approval date not available), where it is used to treat depression, liver disorders, fibromyalia and osteoarthritis.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 10
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 182.63
Molecular weight 399.15
XLogP -2.99
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C[S+](CC1OC(C(C1O)O)n1cnc2c1ncnc2N)CCC(C(=O)O)N
Isomeric SMILES C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N
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
InChI Key MEFKEPWMEQBLKI-AIRLBKTGSA-O

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
IUPAC Name Click here for help
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
International Nonproprietary Names Click here for help
INN number INN
5479 ademetionine
Synonyms Click here for help
AdoMet | S-adenosyl-L-methionine | S-adenosylmethionine | SAM-e | SAMe
Database Links Click here for help
CAS Registry No. 29908-03-0 (source: Scifinder)
ChEBI CHEBI:15414
ChEMBL Ligand CHEMBL224120
DrugBank Ligand DB00118
GtoPdb PubChem SID 178101488
PubChem CID 34756
Search Google for chemical match using the InChIKey MEFKEPWMEQBLKI-AIRLBKTGSA-O
Search Google for chemicals with the same backbone MEFKEPWMEQBLKI
Search PubMed clinical trials ademetionine
Search PubMed titles ademetionine
Search PubMed titles/abstracts ademetionine
UniChem Compound Search for chemical match using the InChIKey MEFKEPWMEQBLKI-AIRLBKTGSA-O
UniChem Connectivity Search for chemical match using the InChIKey MEFKEPWMEQBLKI-AIRLBKTGSA-O
Wikipedia S-Adenosylmethionine