CHEBI:16680 - S-adenosyl-L-homocysteine

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ChEBI Name S-adenosyl-L-homocysteine
ChEBI ASCII Name S-adenosyl-L-homocysteine
Definition An organic sulfide that is the S-adenosyl derivative of L-homocysteine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45495, CHEBI:8945, CHEBI:12741, CHEBI:12759, CHEBI:12761, CHEBI:22034
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Formula C14H20N6O5S
Net Charge 0
Average Mass 384.41204
Monoisotopic Mass 384.12159
InChI InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
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).
EC (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of cyclopropane fatty acid synthase (EC
EC [site-specific DNA-methyltransferase (adenine-specific)] inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of site-specific DNA-methyltransferase (adenine-specific), EC
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing S-adenosyl-L-homocysteine (CHEBI:16680) has role cofactor (CHEBI:23357)
S-adenosyl-L-homocysteine (CHEBI:16680) has role EC [site-specific DNA-methyltransferase (adenine-specific)] inhibitor (CHEBI:65065)
S-adenosyl-L-homocysteine (CHEBI:16680) has role EC (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor (CHEBI:65064)
S-adenosyl-L-homocysteine (CHEBI:16680) has role epitope (CHEBI:53000)
S-adenosyl-L-homocysteine (CHEBI:16680) has role fundamental metabolite (CHEBI:78675)
S-adenosyl-L-homocysteine (CHEBI:16680) is a adenosines (CHEBI:22260)
S-adenosyl-L-homocysteine (CHEBI:16680) is a homocysteine derivative (CHEBI:136505)
S-adenosyl-L-homocysteine (CHEBI:16680) is a homocysteines (CHEBI:24610)
S-adenosyl-L-homocysteine (CHEBI:16680) is a organic sulfide (CHEBI:16385)
S-adenosyl-L-homocysteine (CHEBI:16680) is conjugate acid of S-adenosyl-L-homocysteinate (CHEBI:67009)
S-adenosyl-L-homocysteine (CHEBI:16680) is tautomer of S-adenosyl-L-homocysteine zwitterion (CHEBI:57856)
Incoming S-adenosyl-L-homocysteinate (CHEBI:67009) is conjugate base of S-adenosyl-L-homocysteine (CHEBI:16680)
S-adenosyl-L-homocysteine zwitterion (CHEBI:57856) is tautomer of S-adenosyl-L-homocysteine (CHEBI:16680)
Synonyms Sources
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid PDBeChem
2-S-adenosyl-L-homocysteine HMDB
Adenosyl-L-homocysteine HMDB
adenosylhomocysteine MetaCyc
AdoHcy ChEBI
S-(5'-adenosyl)-L-homocysteine HMDB
S-(5'-adenosyl)-L-homocysteine ChEBI
S-[1-(adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteine IUPAC
S-Adenosyl-L-homocysteine KEGG COMPOUND
S-Adenosylhomocysteine KEGG COMPOUND
SAH MetaCyc
Manual Xrefs Databases
C00007230 KNApSAcK
DB01752 DrugBank
HMDB0000939 HMDB
S-Adenosyl-L-homocysteine Wikipedia
View more database links
Registry Numbers Types Sources
692100 Gmelin Registry Number Gmelin
979-92-0 CAS Registry Number KEGG COMPOUND
979-92-0 CAS Registry Number ChemIDplus
99188 Reaxys Registry Number Reaxys
99188 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
08 March 2017