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:CB1413658, ChemicalBook:CB24796965, ChemicalBook:CB61261439, eMolecules:27677450, eMolecules:474380, ZINC000013550868

Download	Molfile XML SDF

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reading 46 atoms

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46 atoms created

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Wikipedia	License
Paracetamol, or acetaminophen, is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol. Paracetamol relieves pain in both acute mild migraine and episodic tension headache. At a standard dose, paracetamol slightly reduces fever; it is inferior to ibuprofen in that respect, and the benefits of its use for fever are unclear, particularly in the context of fever of viral origins. The aspirin/paracetamol/caffeine combination also helps with both conditions where the pain is mild and is recommended as a first-line treatment for them. Paracetamol is effective for post-surgical pain, but it is inferior to ibuprofen. The paracetamol/ibuprofen combination provides further increase in potency and is superior to either drug alone. The pain relief paracetamol provides in osteoarthritis is small and clinically insignificant. The evidence in its favor for the use in low back pain, cancer pain, and neuropathic pain is insufficient. In the short term, paracetamol is safe and effective when used as directed. Short term adverse effects are uncommon and similar to ibuprofen, but paracetamol is typically safer than nonsteroidal anti-inflammatory drugs (NSAIDs) for long-term use. Paracetamol is also often used in patients who cannot tolerate NSAIDs like ibuprofen. Chronic consumption of paracetamol may result in a drop in hemoglobin level, indicating possible gastrointestinal bleeding, and abnormal liver function tests. The recommended maximum daily dose for an adult is three to four grams. Higher doses may lead to toxicity, including liver failure. Paracetamol poisoning is the foremost cause of acute liver failure in the Western world, and accounts for most drug overdoses in the United States, the United Kingdom, Australia, and New Zealand. Paracetamol was first made in 1878 by Harmon Northrop Morse or possibly in 1852 by Charles Frédéric Gerhardt. It is the most commonly used medication for pain and fever in both the United States and Europe. It is on the World Health Organization's List of Essential Medicines. Paracetamol is available as a generic medication, with brand names including Tylenol and Panadol among others. In 2022, it was the 114th most commonly prescribed medication in the United States, with more than 5 million prescriptions.
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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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