S-adenosyl-L-homocysteine (CHEBI:16680)

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CHEBI:16680 - S-adenosyl-L-homocysteine

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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	ChemicalBook:CB9454820, eMolecules:530768, Selleckchem:pmsf-phenylmethylsulfonyl-fluoride, ZINC000008220691

Download	Molfile XML SDF

more structures >>

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reading 46 atoms

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Wikipedia	License
In biochemistry, phenylmethylsulfonyl fluoride (PMSF) is a serine protease inhibitor (serine hydrolase inactivator) commonly used in the preparation of cell lysates. PMSF does not inactivate all serine proteases. The effective concentration of PMSF is between 0.1 - 1 mM. The half-life is short in aqueous solutions (110 min at pH 7, 55 min at pH 7.5, and 35 min at pH 8, all at 25 °C). At 4˚C, pH 8, PMSF is almost completely degraded after 1 day. Stock solutions are usually made up in anhydrous ethanol, isopropanol, or corn oil and diluted immediately before use. PMSF reacts specifically with the active site serine residue in serine hydrolases. It does not bind to any other serine residues in the protein. This is a result of the hyperactivity of that serine residue caused by the specific environmental conditions in the enzyme's active site (catalytic triad). Because PMSF bonds covalently to the enzyme, the complex can be viewed by X-ray crystallography; it can therefore be used as a chemical label to identify an essential active site serine in an enzyme. Enzyme(active)Ser-O-H + F-SO2CH2C6H5 → EnzymeSer-O-SO2CH2C6H5 + HF Serine protease + PMSF → Irreversible enzyme-PMS complex + HF The median lethal dose between 150–215 mg/kg (acetylcholine esterase inactivator). PMSF should be handled only inside a fume hood and while wearing gloves. DMSO is sometimes recommended as solvent for stock solutions, but should not be used as it makes intact skin permeable to PMSF.
Read full article at Wikipedia

Formula

C14H20N6O5S

Net Charge

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

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

CHEBI:16680 - S-adenosyl-L-homocysteine

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