CHEBI:16680 - S-adenosyl-L-homocysteine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name S-adenosyl-L-homocysteine
ChEBI ID CHEBI:16680
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
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
InChIKey ZJUKTBDSGOFHSH-WFMPWKQPSA-N
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: yeast.sf.net 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.
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).
EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of cyclopropane fatty acid synthase (EC 2.1.1.79).
EC 2.1.1.72 [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 2.1.1.72.
epitope
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 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor (CHEBI:65065)
S-adenosyl-L-homocysteine (CHEBI:16680) has role EC 2.1.1.79 (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)
IUPAC Name
S-(5'-deoxyadenosin-5'-yl)-L-homocysteine
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-ADENOSYL-L-HOMOCYSTEINE PDBeChem
S-Adenosylhomocysteine KEGG COMPOUND
SAH MetaCyc
Manual Xrefs Databases
ADENOSYL-HOMO-CYS MetaCyc
C00007230 KNApSAcK
C00021 KEGG COMPOUND
DB01752 DrugBank
HMDB0000939 HMDB
S-Adenosyl-L-homocysteine Wikipedia
SAH PDBeChem
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
11700066 PubMed citation Europe PMC
11746687 PubMed citation Europe PMC
11961214 PubMed citation Europe PMC
11997462 PubMed citation Europe PMC
12767735 PubMed citation Europe PMC
15026045 PubMed citation Europe PMC
15057524 PubMed citation Europe PMC
15542683 PubMed citation Europe PMC
15645450 PubMed citation Europe PMC
16109423 PubMed citation Europe PMC
16197293 PubMed citation Europe PMC
16197315 PubMed citation Europe PMC
16253211 PubMed citation Europe PMC
16423634 PubMed citation Europe PMC
16519522 PubMed citation Europe PMC
17044778 PubMed citation Europe PMC
17172447 PubMed citation Europe PMC
17300772 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
17726531 PubMed citation Europe PMC
18976670 PubMed citation Europe PMC
19249293 PubMed citation Europe PMC
19357721 PubMed citation Europe PMC
21837278 PubMed citation Europe PMC
22225784 PubMed citation Europe PMC
22455498 PubMed citation Europe PMC
24145794 PubMed citation Europe PMC
Last Modified
08 March 2017