CHEBI:15414 - S-adenosyl-L-methionine

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ChEBI Name S-adenosyl-L-methionine
ChEBI ID CHEBI:15414
ChEBI ASCII Name S-adenosyl-L-methionine
Definition A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45607, CHEBI:10833, CHEBI:12742, CHEBI:12760, CHEBI:12757, CHEBI:22036, CHEBI:10786, CHEBI:8946, CHEBI:527887
Supplier Information ChemicalBook:CB2852025, ChemicalBook:CB61017625, ChemicalBook:CB4362168, eMolecules:475725, ZINC000005133329
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Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
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Formula C15H23N6O5S
Net Charge +1
Average Mass 399.44500
Monoisotopic Mass 399.14452
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
InChIKey MEFKEPWMEQBLKI-AIRLBKTGSA-O
SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12
Metabolite of Species Details
Mycoplasma genitalium (NCBI:txid2097) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Mycoplasma genitalium metabolite
Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
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ChEBI Ontology
Outgoing S-adenosyl-L-methionine (CHEBI:15414) has role Mycoplasma genitalium metabolite (CHEBI:131604)
S-adenosyl-L-methionine (CHEBI:15414) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
S-adenosyl-L-methionine (CHEBI:15414) has role coenzyme (CHEBI:23354)
S-adenosyl-L-methionine (CHEBI:15414) has role cofactor (CHEBI:23357)
S-adenosyl-L-methionine (CHEBI:15414) has role human metabolite (CHEBI:77746)
S-adenosyl-L-methionine (CHEBI:15414) has role micronutrient (CHEBI:27027)
S-adenosyl-L-methionine (CHEBI:15414) has role nutraceutical (CHEBI:50733)
S-adenosyl-L-methionine (CHEBI:15414) is a sulfonium compound (CHEBI:26830)
S-adenosyl-L-methionine (CHEBI:15414) is conjugate acid of S-adenosyl-L-methioninate (CHEBI:67040)
S-adenosyl-L-methionine (CHEBI:15414) is enantiomer of S-adenosyl-D-methionine (CHEBI:156255)
S-adenosyl-L-methionine (CHEBI:15414) is tautomer of S-adenosyl-L-methionine zwitterion (CHEBI:59789)
Incoming S-adenosyl-S-carboxymethyl-L-homocysteine (CHEBI:136699) has functional parent S-adenosyl-L-methionine (CHEBI:15414)
(R)-S-adenosyl-L-methionine (CHEBI:33440) is a S-adenosyl-L-methionine (CHEBI:15414)
(S)-S-adenosyl-L-methionine (CHEBI:33442) is a S-adenosyl-L-methionine (CHEBI:15414)
S-adenosyl-L-methioninate (CHEBI:67040) is conjugate base of S-adenosyl-L-methionine (CHEBI:15414)
S-adenosyl-D-methionine (CHEBI:156255) is enantiomer of S-adenosyl-L-methionine (CHEBI:15414)
S-adenosyl-L-methionine zwitterion (CHEBI:59789) is tautomer of S-adenosyl-L-methionine (CHEBI:15414)
IUPAC Name
[(3S)-3-amino-3-carboxypropyl](5'-deoxyadenosin-5'-yl)(methyl)sulfonium
Synonyms Sources
(3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt ChemIDplus
[1-(adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium IUPAC
Acylcarnitine KEGG COMPOUND
AdoMet JCBN
S-(5'-deoxyadenosin-5'-yl)-L-methionine JCBN
S-Adenosyl-L-methionine KEGG COMPOUND
S-adenosyl-L-methionine ChEBI
S-Adenosylmethionine KEGG COMPOUND
S-adenosylmethionine ChEBI
SAM JCBN
SAMe ChemIDplus
Manual Xrefs Databases
C00007347 KNApSAcK
C00019 KEGG COMPOUND
DB00118 DrugBank
HMDB0001185 HMDB
MOL000172 COMe
S-Adenosyl_methionine Wikipedia
S-ADENOSYLMETHIONINE MetaCyc
View more database links
Registry Numbers Types Sources
29908-03-0 CAS Registry Number KEGG COMPOUND
29908-03-0 CAS Registry Number ChemIDplus
3576439 Beilstein Registry Number Beilstein
3919754 Reaxys Registry Number Reaxys
Citations Types Sources
11017945 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
Last Modified
26 July 2019