S-ADENOSYL-L-HOMOCYSTEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H20N6O5S
Molecular Weight	384.411
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C(N)N=CN=C23)C(O)=O

InChI

InChIKey=ZJUKTBDSGOFHSH-WFMPWKQPSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15057524 | https://www.ncbi.nlm.nih.gov/pubmed/28684218 | https://www.ncbi.nlm.nih.gov/pubmed/10400831

S-Adenosyl-L-homocysteine (SAH), a potent methyltransferase inhibitor and a substrate of the s-adenosylhomocysteine hydrolase, is an amino acid derivative and an intermediator or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It was shown, that the plasma SAH might be a novel biomarker for the early clinical identification of cardiovascular disease. In addition, the elevated SAH in Alzheimer's brain was related to markers of disease progression and cognitive impairment.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosylhomocysteinase 5 Target ID: P23526 Gene ID: 191.0 Gene Symbol: AHCY Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28933241	Substrate 661
Phosphatidylethanolamine N-methyltransferase 1 Target ID: Q9UBM1\|\|\|Q9Y6V9 Gene ID: 10400.0 Gene Symbol: PEMT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7278517	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28684218	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15057524	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis, mechanism of action, and antiviral activity of a new series of covalent mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase.	2001 Aug 16	11495586
DNA (cytosine) methyltransferase overexpression is associated with acquired drug resistance of murine neuroblastoma cells.	2001 Feb	11172599
Homocysteine metabolism in children with Down syndrome: in vitro modulation.	2001 Jul	11391481
Effects of methylmercury and organic acid mercurials on the disposition of exogenous selenium in rats.	2001 Jul 15	11446833
Blood determinations of S-adenosylmethionine, S-adenosylhomocysteine, and homocysteine: correlations with diet.	2001 Jun	11401915
Identification of the active oligomeric state of an essential adenine DNA methyltransferase from Caulobacter crescentus.	2001 May 4	11278726
Targeting "hydrolytic" activity of the S-adenosyl-L-homocysteine hydrolase.	2001 Sep	12369977
Increasing levels of dietary homocystine with carotid endarterectomy produced proportionate increases in plasma homocysteine and intimal hyperplasia.	2001 Sep	11500183
High dietary folate supplementation: effects on diet utilization and methionine metabolism in aged rats.	2002	11813082
RNA:(guanine-N2) methyltransferases RsmC/RsmD and their homologs revisited--bioinformatic analysis and prediction of the active site based on the uncharacterized Mj0882 protein structure.	2002 Apr 3	11929612
Altered levels of S-adenosylmethionine and S-adenosylhomocysteine in the brains of L-isoaspartyl (D-Aspartyl) O-methyltransferase-deficient mice.	2002 Aug 2	12023972
3-deazaneplanocin A induces massively increased interferon-alpha production in Ebola virus-infected mice.	2002 Jul	12076759
Quantification of plasma S-adenosylmethionine and S-adenosylhomocysteine as their fluorescent 1,N(6)-etheno derivatives: an adaptation of previously described methodology.	2002 Jul 31	12093531
Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase.	2002 Jun	12084826
Catechol-O-Methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: importance in pathophysiology and pathogenesis.	2002 Jun	12083324
Interaction of S-adenosylhomocysteine hydrolase of Xenopus laevis with mRNA(guanine-7-)methyltransferase: implication on its nuclear compartmentalisation and on cap methylation of hnRNA.	2002 Jun 12	12063172
Catalytic mechanism of S-adenosylhomocysteine hydrolase. Site-directed mutagenesis of Asp-130, Lys-185, Asp-189, and Asn-190.	2002 Jun 21	11927587
Diethanolamine induces hepatic choline deficiency in mice.	2002 May	11961214
Characterization of human soluble high and low activity catechol-O-methyltransferase catalyzed catechol estrogen methylation.	2002 Oct	12360102

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

S-ADENOSYL-L-HOMOCYSTEINE

Common Name

English

S-ADENOSYL-L-HOMOCYSTEINE [USP-RS]

Common Name

English

L-HOMOCYSTEINE, S-(5'-DEOXYADENOSIN-5'-YL)-

Systematic Name

English

S-(5'-ADENOSYL)-L-HOMOCYSTEINE

Systematic Name

English

ADENOSYLHOMOCYSTEINE

Common Name

English

Classification Tree Code System Code

LOINC

80174-6